Updated on 08.27.14

Piecing Through A Major Life Decision

Trent Hamm

Right now, I’m sitting at a crossroads as to the future direction of my career and, by extension, my life.

The Decision

Throughout my life, I’ve harbored a dream of being a professional writer. I’ve always felt a great deal of power and of emotional release in the written word, dating back literally to my early grade school years when I would write very long letters to relatives and to several pen pals that I had who were in nursing homes. A few key people along the way, namely my late great uncle and my high school English teacher, offered me the right kind of encouragement at the right time to keep that flame alive, but I made other choices in life and followed a completely different career path, one that I’m quite content with.

On a lark, I started The Simple Dollar, intending to just write about personal finance in my spare time. Somewhere along the way, it took off beyond my wildest dreams and now brings in about one and a half million page views a month just to the site alone, not counting the over 10,000 RSS subscribers and nearly 10,000 email subscribers. The sheer volume of visitors, which has come about without any advertising, without me having any sort of media presence at all, without any networking, or anything else, indicates that something is going on. What that something is, I don’t profess to fully understand, but something I am writing is striking a chord with someone somewhere.

Here’s the decision, then. Do I take that as a sign that I have enough value as a writer to make that my career, or do I follow the safe road and continue doing what I’m doing? It’s a debate that I’m struggling with a great deal internally, and one that is also challenging my wife, too.

What Making This Leap Would Entail

I’m a planner – I can’t help myself. I’ve carefully thought about and considered what I would do if I did decide to make the jump to a full-time writing career.

I’d continue The Simple Dollar, obviously

While I don’t make enough revenue from this site for me to ever feel “safe” about it, I do make a bit of revenue, enough so that with my wife’s salary and my frugal choices, we would be fine at home. However, my dreams for being a writer don’t revolve around sitting around all day just thinking of blog posts on personal finance issues.

I’m also currently involved in some offline writing projects

This includes contributions to several different print media sources. Most of these are paid opportunities, and I hope to build on them as time allows.

I also have a completed book proposal and am seeking a literary agent

I feel that I have a story worth telling that builds into some strong advice for people who were where I was at two years ago, advice that I haven’t really seen gel together in a book anywhere else. Again, this is something completely new to me and I’m learning about how such things work as I go along.

My next move would be to start an instruction-oriented cooking blog

In fact, that’s part of why I wrote an entry earlier this month about making a loaf of bread. It let me think about how I would want to write about food preparation in a blog form, while writing something instructional and relevant to the frugal-minded audience of The Simple Dollar. My idea is to write one entry a day in a format something like that bread recipe, with later entries building upon some of the content of earlier entries. This would enable me to extend my passion for cooking and also for writing.

I have some other projects on the far back burner as well, but this outlines my immediate plans if I were to make the leap.

Why I Should Make The Leap

1. My current responsibilities are causing me to burn the candle at both ends

I currently handle my real job during the day, spend time with my family in the early evening, and sleep a limited amount at night, and I squeeze in The Simple Dollar and other writing responsibilities in the slivers of time around this, mostly in the early morning when the house is quiet, late in the evening, in an hour or so slot after I get home but before my family does, and usually one afternoon a week. While I’ve not burnt out on this schedule yet, I feel that it could lead to burnout, and I’ve felt it coming close more than a few times.

2. My tentative plan involves me spending more time with my children

Our current plan not only would free up time that I could spend with them, but it also includes two days a week that I spend effectively as a stay at home dad. We would still take our children to daycare three days a week, but for the other two, the kids would stay home with me. I want to just spend a lot of quality time with them, taking them to the library, reading to them, playing outside with them, fixing them lunch, and so on. Plus, switching to this plan enables me to be there for them when they’re sick, rather than the constant battle my wife and I often have when one of us has to take time off for child care.

3. This whole plan reduces our costs drastically

A solid portion of our daycare cost vanishes. My transportation costs to and from work vanish. Our food costs go down, since we’d almost exclusively eat freshly prepared meals at home instead of the mix of home-cooked meals, take out, and other things that we eat now. My temptation to spend goes down drastically, too, since I’m not tempted by driving through commercial sections of cities near where I live any more.

4. The sky is the limit

How far could this really go? I don’t know, but I do know that giving it my full attention will provide more fuel than what I’m giving it right now.

Why I Shouldn’t Make The Leap

1. It’s a very sharp decrease in financial stability

Our income would become much less stable and we’d have to rely quite a bit on our own frugality to get us through. I think our financial pillow right now is pretty solid and our debts are melting away quite nicely right now (which further reduces required monthly expenses), but the loss of stability is unnerving, particularly with two children and a decent-sized mortgage.

2. I’m not sure how far my writing can take me

In the past when I’ve mentioned this idea, readers have immediately criticized my writing. To be fair, much of my writing for The Simple Dollar is not polished, finished writing. I often take what I’m feeling, organize the thoughts, give the sentences a quick review, and publish. To me, that’s how blog writing should be done, because blogs are about the idea churn, not about publishing finished pieces that you’d want to submit to The New Yorker. They need to be readable and accessible and logical, but grammatical perfection and ideal word choices aren’t always necessary here. In the print world, they’re much more important. Can I carry whatever knack I have for assembling written things here and carry it over to print media? I believe I can and I’ve seen early signs of it, but in many ways it is a different ball game.

3. I’m afraid of burn out and regret

I’ve been writing fervently here for more than a year and I feel like the fire is just getting started, but I’m betting the future on that fire continuing. Will it? I’m not certain.

4. To a great extent, I like what I’m doing now

here are intellectual and creative challenges there that I quite enjoy and I would deeply miss if I walked away. I have considered a part time approach, but I’m pretty sure that many of the aspects that I enjoy the most would vanish if I went that route, as the creative space would shrink quite a bit.

So What Do I Do?

To be quite honest, I’m not sure. I’m planning on spending this Thanksgiving doing some serious soul-searching and talking about these issues with the people whose opinions I value the most in my life, namely my wife, my parents, and my wife’s parents. I hope that by the end of the Thanksgiving weekend, I will have come to a decision on this. I know that it’s been the top issue on my mind for a while now and I need to really figure out what direction I’m going and put my full heart and soul behind it.

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  1. Heidi says:

    I admire what you’ve done in such a short time with TSD, but I don’t envy your position. As the primary earner in my family, I dream of the day that I can achieve FI and get off the treadmill and consult/speak at my leisure, but I think I am too chicken to ever give up my benefits (besides, I mostly love my job).

    You seem like a deliberate, thoughtful individual and no matter what choice you make, I know it will be the right one.

    Good luck.

  2. Joe says:

    Trent, if you want to quit your day job, you had better have ideas other than this website. While, I love thesimpledollar.com, there are only so many things in the personal finance world that you can write about and there are anyways tons of sites out there doing exactly the same thing as this one. At some point, you’re just not gonna be able to churn out meaningful content and there are only that many books that you can review…

  3. DebtyBetty says:

    Is your “day job” something that you could easily slip back into if your leap doesn’t work out as hoped?

  4. finkle says:

    Trent, how fortunate for you to be in such a pickle! This is a decision so many of us would love to have to face, and there is a measure of envy as I write this.
    When I made the decision to go to nursing school, I wondered if I was going to make it in such a competitive environment. I knew the rewards would be great, but I was apprehensive. After much discussion I realized I could count on only taxes and end of life to happen, everything else was a crap-shoot.
    Whatever your decision, I’ve no doubt it’s gonna be the right one! I’ve been reading you for some time now, and have faith in you!

  5. Mrs. Micah says:

    Well, at least you’re thinking the right things on both sides of the argument. DebtyBetty has a point as to whether you might be able to get back into your field if this doesn’t work out.

    And I think the step-by-step cooking blog sounds really cool! I enjoyed your bread recipe, it was straightforward and I bookmarked it just in case. :)

  6. dimes says:

    First of all, I would NOT do this if your household cannot float solely on your wife’s income. Is her job stable? Is she the primary breadwinner currently?
    Also, I’m confused about the childcare situation. Are you saying that if you pursued full-time blogging you’d still need childcare three days per week? Whatever for? Shouldn’t you be available all the time? (Granted, being a SAHP will not allow you to be anywhere near as effective time-wise as you might think, since kids require a lot of your attention.)
    Third, how big is your emergency fund? If you quite your job next week and then your wife got fired from hers on January 1, how long could you survive on your emergency fund (any blog revenue and tax refunds excluded)? If it’s not 3-6 months, you don’t have enough to make this leap right now.
    Fourth, have you considered compromise? Do you have a job you could cut back to part-time with? I don’t know what you do for a career, but if it’s something that you can slip to part-time, maybe you can free up more time for blogging while not sacrificing “guaranteed” income altogether. Alternatively, you could switch to a *different* job/career field and do that on a part-time basis. There’s no problem with working at Target 15 hours per week while pursuing another dream.
    Fifth, what kind of a writer are you hoping to be? A pump-and-dump romance writer? A Kiyosaki fraud-series writer? A Touched-by-the-Oprah writer, like Dr Phil or David Bach/Suze Orman? A publish it yourself and hope Simon and Schuster wants to make a gamble on you writer? A great American Novel writer? Some columnist for the Ottumwa Weekly? They’re all very different, and deciding what exactly you want to do will help you figure out the best way to try and get there.
    I think until you know WHAT you want to do, HOW you are going to do it, and have a solidly crafted PLAN (and a fat emergency fund), you shouldn’t give up your job for full-time writing. Once you have a plan AND have consulted with people qualified to give you advice (ie, a licensed financial planner and a literary agent/evaluator/critic), THEN you should consider forsaking all others to pursue this dream.

  7. Paul says:

    Man, do I really know how you feel. I am a stay at home dad (for the moment,) and my wife is the primary earner. We moved away from our pretty well set life in Tucson, AZ to live in a much smaller town in Illinois (and also a much less active job market,)and overall it has been a good change for us. I have picked up a lot of tips at TSD and we are living much more frugal then we ever did in AZ. Things are going well for us and I really believe that if you want something bad enough you can attain it. I now only work a PT night job a few nights a week and that gives me way more home time than I used to have.
    I guess what I’m really trying to say is I think you should go for it. Try it w/o working and if that isn’t going so well perhaps get a PT 20hr/wk job to supplement your income. If all else fails, you could always go back to a full time job.
    Somebody told me something once that has stuck w/me for years and perhaps it is worth writing here:
    “Live for today because yesterday is gone and tomorrow may never come.”

  8. Catherine says:

    “I think our financial pillow right now is pretty solid..”

    Watch those mixed metaphors! :)

  9. LC says:

    I don’t know what field you work in, but is there a possibility of working part time or job sharing with another person in the same situation? This way you still stay current in case you end up wanting to go back, or at the very least ease the transition to full time writing/staying home.

    I know many people who found that part time work was the perfect balance for them. If that isn’t possible at your company, is there another job you are qualified for that would allow you to work part time? Even if your company doesn’t have a set policy, it might be worth bringing it up with HR/your boss to see how they feel about it. Many times they would rather do this than lose a talented worker altogether.

    You have enough money sense to make it on a lower income, and maybe your wife could look for more opportunities. My advice would be to do what you know you will be more passionate about. If you are just going to work because it pays the bills, and you could easily survive if you chose to do something else, do something else. Life is too short to spend it doing something you don’t love if there is another option.

    In addition, those precious years while your children are young will be gone in just a little while. Enjoy it while you can, and then if you end up needing/wanting to go back to work when they are older, I think the decision will be easier.

    I wish you luck in your decision. I think you know deep down what the right solution is for your family.

  10. Beth says:

    Good luck with your planning ahead! It might be a good idea to get enough money set aside that your wife’s income and money taken from that account can cover you for the first 6-12 months, rather than planning on using money from TSD. On the other hand, you can plan and plan and plan but at some point you’ve got to fish or cut bait.

    And I think it’s smart to recognize that you’re quitting work but still need dedicated working time – it would be unfair to your kids to have them home every day only to be frustrated that they actually need attention :)

  11. Kim says:

    Sounds like your talking about working from home part time ( for yourself), and being the sah parent part time which is a nice compromise. If you can live off your wife’s income and potentially get back to your field if need be I say go for it. Your children will be in school fulltime very quickly and if the venture doesn’t go like you planned the worse that happens is that you have to go back and get that other job. Be forewarned that working for yourslf is totally addictive! Best Wishes!

  12. Writers Coin says:

    I’m curious about the type of writer you want to be too. Magazine articles? About finance and cooking? Or a literary writer? If it’s the latter, please please let us know.

    And welcome to the dark side.

  13. Mark says:

    This blog became successful for a reason, take that as a sign. An opportunity such as this does not come along very often.

  14. Erin says:

    Your arguments for making the move are pretty solid. The only item I didn’t see discussed is health insurance. Can you afford the additional cost of adding yourself to your wife’s health insurance plan? Are both children already on her plan? Can you afford the COBRA payments if she were to lose her job?

    You definitely don’t want to be without quality insurance with two young children. You never know when anyone in your family could suffer catastrophic illness or injury.

    Also keep in mind that advances for books aren’t usually very high and it takes a long time for royalties to be paid. For non-fiction, you’ll also be expected to do a lot of promotion, only some of which (if any) will be paid for by your publisher.

  15. Margaret says:

    What do you value most?
    Family? Career? Perhaps you can have both.

    Although leaving your day job may cause a temporary shake for your financial situation, I believe if you continue to work hard doing what you do so well and love so much (writing), that everything will be okay. You may, of course, want to discuss this with your family first, as there is a risk that the financial situation may, in the beginning, take a dip. Explain to them the effects this may have on them, and talk about the decision together.

    In the end, just consider that your kids will grow up, and if what you’re currently doing isn’t fulfilling you, then a change should be made so that it is. Is it this particular change? That’s your ultimate decision, but don’t let fear stand in the way of your dreams.

    Best of luck!

  16. Mike says:

    I’m convinced you can do it, Trent. The writing on TSD is compelling enough to bring me back day after day. Judging from the work you do here, I’d say your writing is much better than that in a large number of the books I buy.

    Would it be possible to take a one-year unpaid leave of absence from your job? I’ve known several people who have done so and have been surprised that their employers said yes. It’s worth a try; it would give you peace of mind to know you could go back to work if writing didn’t pay the bills or if you weren’t happy being home all the time.

  17. Ernesto says:

    I agree with Erin that the primary issue you’ll face is health care. If the wife unit can provide it through her work then you’re golden.

    If you take the plunge, you’ll discover the best kept secret of the US tax code: it was written by business people for business people. Everything that was a cost now becomes a expensable item. When I started my first business, I was shocked how much my tax bill dropped. Keep good records and you’ll need maybe half your current income to maintain your style of living.

    My advise, take the plunge; if it doesn’t work out, go get your corporate job back, it’ll still be there.

  18. Elizabeth says:

    What an exciting crossroads! Scaling down your hours at your current job might let you test the writing career waters some more while building up more of a cushion before you make a full jump.

    In addition to exploring the option of working part time for your current job, if it’s a business that has crunch times (especially foreseeable ones), you could also offer working as a seasonal contractor for them just during the crunch time. I do a combination of the 2: half-time most of the year (just enough for health insurance), with the understanding that during my company’s annual proposal-writing crunch my hours will go way up.

    The key to any of this is having a workplace that a) will work with flexible work schedules and b) adjusts expectations accordingly so that you don’t end up working 40 hours a week and getting paid for 20.

  19. vh says:

    Trent… Unless you have a source of income that will pay the mortgage and put food on your table and a spouse with a job that provides health insurance, think this through carefully. (That’s a way of saying “Stay away from the edge of the cliff!”)

    I am a professional writer. I made my living, after a fashion, as a writer for quite a few years. I’ve written a book on feature writing (one of several books published under my name and others’ that I’ve cranked out) and over the years have published more regional & national magazine and newspaper articles than I can count. The freelance writing gig was supported by a husband who earned in the six figures and could afford to support me, our kid, and himself in the style to which he intended to remain accustomed. The writing skills weaseled me into editorial jobs at my state’s largest city magazine and later at what was then the largest & most respected regional magazine in the U.S.

    HowEVer…. Once I made my escape from the gilded cage, m’dear: there was noooo chance on God’s green earth that I could support just myself (kid not included) on what I could earn as a writer. Income for fulltime freelance writers averages around 10 grand a year and hasn’t increased in 30 years.

    Why, you ask? Well, as an editor lemme tell you why: Because the woods are full of marginally bright ego-deprived folks who will write for free, or almost free, just for the privilege of seeing their names in print. You are competing for people who will work for NOTHING!

    In an environment like that, you cannot earn a living unless you live (alone, with no dependents, and about as close to the bone as Tight-Fisted Miser lives) in New York City.

    Luckily for me, I finished a Ph.D. while I was married to the corporate lawyer, and even more luckily, shortly after the escape I stumbled into a f/t nontenurable university teaching job that, by five years ago, paid a munificent 43 grand a year. You & your family probably can live on that…but I don’t live in the Midwest; I live in a pricey urb. After 10 years on the job, I managed to weasel into a quasi-administrative editorial job on a larger campus that pays about 15 thou more than I earned as a teacher and requires about half as much work. Pay is better, but with retirement looming I just make ends meet while I pack every extra pinched penny into savings but still am looking at a $10,000 cut in pay when I do retire in three years.

    Both these last two jobs provide health insurance, something that you will have a fine time getting for yourself as a freelance scribe in the Midwest. A couple of trade groups–Writer’s Guild and the American Society of Journalists & Authors–offer group insurance (put your wife to work so you can pay for it), but the providers tend to restrict coverage to the East Coast.

    Dear lord. Don’t quit your day job!

  20. Michael says:

    I would say The Simple Dollar is not yet successful enough.

  21. Kalieris says:

    No advice, just wishing you well on whatever you decide to do.

    (Ok, maybe a little advice: Dreams are important things, and if there is any way you can act on yours, do so. If worst comes to worst, you can always get another day job.)

  22. At some point in each of lives there comes a time when we must take a leap of faith towards something we believe in. You did it when you got married. You can do it again with making this site into a full time venture! God speed!

  23. Erica says:

    Jump now, fortune favours the brave.

    You can always go back to being an employee, the time may never be as ripe to branch out on your own.

    Good Luck

  24. I might get reamed by other readers, but let me comment from a spiritual perspective: Sometimes God asks us to do things that seem absolutely nuts to us. Think Noah or Abraham. But the end result is more than we could ever imagine. Doesn’t mean it’s always easy, but being obedient is always the best thing. My husband and I recently relocated here to the US. Before we left NZ we had no job to go to, no house to live in and about four months expenses saved up. People thought we were CRAZY. But it was the most joyous decision we have ever made.
    And something my dad has told me, a very financially wise man – it’s just money, you can make more.

  25. pc says:

    Monetary issues are very important to consider but I haven’t seen anyone address personal issues. At one point in my life, I encouraged my husband to quit his job [for several very valid reasons]. We could afford for him to do this because I have always made quite a bit more money than he has. He also did not quit without a plan – he took a year off to stay home with our daughter & evaluate his options and then another year to get a teaching credential. HOWEVER, even though I was the one who suggested he follow this path, at times I was jealous that he was able to be a SAHP and I couldn’t. In fact, to this day when he has holidays and summers off with our children, I am still jealous and wish it were me who could stay at home with them. Don’t get me wrong – I am very glad that at least one of us can do this. I just wish it could be me. Unfortunately, the disparity in salary between a teacher and an MBA is too great for that to happen.

    No matter how liberated, educated, or well-salaried a woman is, there is always a part of her [I believe] that wishes she could be a stay at home parent. So, my suggestion is that you discuss with your wife at length this aspect of your becoming a work-at-home parent, and make certain that you & she are prepared for that issue to arise.

  26. Pauline says:

    Trent — I’ve been reading your site for most of the past year and have forwarded links several times to my 20-somthing adult children who might learn from your experiences (yes, I’m old enough to be your mother…). My advice to you is: GO FOR IT! Build up your reserve fund to a level that you feel would handle any foreseeable house or medical crises, keep all of your insurance up to date, and make a contract with your wife to give it a solid try for 2 years, then re-evaluate. If you don’t, you’ll always wonder if you could have. Your children are very young; they will profit much more from your day-to-day presence in their lives than they will from whatever other money you will earn, and their needs are very simply met right now. There will not be another opportunity in your life that feels safer to make this leap for a long time. You have the potential to be a really good writer. DO IT.

  27. Diane says:

    Have you ever thought of charging a fee for the Simple Dollar? It could be free for the first month so people could see if they liked it. Then you could charge say 5 or10 bucks for a year. It could be like an online magazine with forums etc. That would create a little ching!

  28. J.D. says:

    Trent, I feel like you and I have had some good talks on this subject. Based on what you’ve shared of your situation, I’d say: MAKE THE LEAP! I know you don’t have the career safety net that I have, but you have other advantages.

    It’s been a couple weeks since I made my decision. It’s been liberating. Suddenly I have all sorts of personal goals that seem obvious, whereas before they were clouded by the need to work at the day job.

    I think your cooking blog idea is outstanding. It’s something you’re passionate about, and people obviously are drawn to your explanations. And you know the great thing about it? It’s also the kind of thing you wouldn’t have to write every day. Once or twice a week would be perfect.

    As always, I’m here to chat if you need it.

  29. holli jo says:

    What an exciting choice for you! I have loved your site ever since I found it, and I think you could definitely make it as a writer.

    I just made the leap two months ago to become freelance writer myself, and it’s been wonderful so far. (Though I did not have the benefit of time for planning and transitioning slowly into the lifestyle. I lost my job and didn’t find another one, so I was forced to make one of the best decisions I’ve ever made!)

    Anyway, you will know in your heart what the right answer is for you. Don’t let fear get in the way of your dreams. Do what is right for you and your family!

  30. I completely agree with Michele@Philoxenos. Where do you feel God is leading you? He gave you a talent as a writer, and that is demonstrated by how successful The Simple Dollar has become.

    If it’s always been a dream of yours to be a writer, don’t let fear hold you back. As stable as your current job seems, nothing is ever certain. I don’t know what you do for a living, but companies change owners, the economy changes, buildings burn down…nothing is certain.

    You can always go back to work doing something other than writing if the writing career doesn’t take off. But you don’t want to be an elderly man, looking back at your life wondering what would have happened if you had given it a try.

  31. DeeAnn says:

    Trent, I hope you don’t burn out, burning the candle at both ends. I enjoy your writing on the blog.

  32. Becky says:

    I’m new to this site, but I love it. I think you should go for it!!! My only question, are you really close to having those debts paid off (besides the mortgage)? It would be nice to go into something like this debt-free.

  33. SJean says:

    If you decided to do it, good luck!
    If you don’t do it YET, that doesn’t mean you can’t do it a little bit later on.

  34. girlrobot says:

    i say go for it. i really hope you start a frugal cooking blog as there is a definite need for a GOOD one out there! best of luck whichever route you go!

  35. debtheaven says:

    This is really funny because I’ve read either you saying you should read Get Rich Slowly more, or him say he should read The Simple Dollar more, because you’re both similar. Sorry, but I can’t remember who said it, I’m thinking that over time maybe both of you said it.

    As a reader of both blogs, I’m sometimes surprised at how often you both bounce off each other. I think it’s unconscious, and I’m sure you both show up regularly on Carnivals and such (which I don’t read).

    All this to say:
    – He just decided to trade in his day job for his blog. BUT he’s giving himself ONE YEAR TO DO THAT.

    – They don’t have kids, they don’t want kids. No kids = less expenses.

    – A few weeks ago you were talking about you or your wife eventually maybe becoming a SAHP. If you make this leap, then the decision is made, and possibly irrevocable. I’m assuming your wife is OK with that? That if and when you have your third child, she will pick up her briefcase and you’ll contentedly kiss her goodbye at the door?

    – I can’t help but wonder how offering your SIL to live with you permanently ties into this. Maybe it’s totally unrelated, but both questions came up extremely close in time.

    Good luck, whatever you decide!

  36. !wanda says:

    I second the idea of asking for an unpaid leave of absence for a year.

  37. Susy says:

    My husband left his job 5 years ago to start his own business. It was the best decision ever made.

    We would never give up working from home for a minute, we do however work more now than we ever did before.

    If you think you can swing it, do it. We wished we would have done it sooner.

    One piece of advice. If you are the kind of person that values security, having a large cushion will save much stress and make it much more enjoyable to be self-employed! We had to cut back on adding to our savings for a couple years, but we made it through and now our business is doing really well. We are at the point where we can max out our retirement and save a lot as well as pay all of our bills with no problem.

  38. MS says:

    No advice, but good luck (and wisdom) on your decision.

  39. RNA says:

    On CNBC yesterday, John Bogle put the chance of a recession at 75%. Maybe with the ethanol boom in Iowa, yours or your wife’s industry would be untouched, but be cautious of the timing.

    Also, I have to disagree that your experience going into and out of significant debt is very unique. And your debt-relief methodology has been derived from excellent books like “Your Money or Your Life”. What have you added that is original? You do have a Martha Stewart-like level of energy that might be what you need to rise above the thousands of other people writing in this space, and TSD website is much more organized and readable than others of its ilk. Good luck with your decision.

  40. miguel says:

    My advice to you is to take a few days off. Get away from all work for a few days, and try not to think about it for a few days. This will let you step back from your normal routine, and figure out what’s important.

  41. Maureen says:

    I’ve never left a comment on this site before, but had to come out of hiding for this post.

    I don’t remember when or how I stumbled upon The Simple Dollar, but at the time I wasn’t even really interested in personal finance. I kept coming back, and eventually became an RSS subscriber, because, well, you’ve got a gift. You write well, you’re able to pick compelling topics, you make what you write about relevant to a broad cross-section of people, you have a nice personal touch without being too personal; it all works together really well. Because of your blog, I’ve gotten interested in personal finance, checked out other resources, and made some good improvements in our family’s financial life. I imagine there are quite a few other people out there, among your approximately 20,000 or so regular readers(!), who would echo my comments.

    Now might not be the time, full-time might not end up being the way to go, etc. etc. No matter what you decide at this point, though, it seems that you like writing and that people like and appreciate what you write. So I hope you keep it up.

  42. tambo says:

    Trent, I have no idea if you’re considering a career writing fiction or non fiction – I hope it’s NF, because you definitely have a knack for that – but if it’s fiction, please, please, PLEASE take a good solid look at your life, finances, and family responsibilities before taking the leap. The fiction market can be rough, the pay stinks in comparison to the work, and the competition just to get noticed by an agent or editor is enormous. Add in the pressure to have each book earn more than the last, the demands of marketing, public appearances – all on your dime, not the publisher unless you’re a big name – and the sheer amount of TIME involved, it’s not an easy life for the writer or the writer’s family. MOST books lose money, MOST working writers make well under $5k a year, and MOST working writers spend a lot more than 40 hours a week on the job. Sure, we’ve all heard of Nora Roberts and Stephen King making tons of cash, but they’re the anomaly, not the norm. This is not a job that you can budget around, not unless you’re churning out several books a year. And you have two small children. Publishers don’t care if the kids have the flu or have decided to dismantle the kitchen, and kids don’t understand what a deadline or tele-marketing meeting is.

    I’m not saying it’s impossible, but writing a few blog posts a day is nothing like writing a book, on contract, with deadlines, length, and content specifications to meet, edits, another book due right after, marketing, interviews, travel, *and* keeping a family happy.

    Don’t even consider quitting your job until you have a publishing contract in hand because, honestly, 98% of all aspiring writers NEVER sell, and if they do it’s to a small press or epub which don’t pay hardly anything, if at all. I write mass-market paperback mysteries for a major publisher with worldwide distribution, and there is absolutely no way I could write full time without my husband being able to support us. One friend writes ten or more novels a year, many as a ghost writer, just to pay her mortgage.

    I’m all for following your dreams, just please, take your time. Your kids are only little once. I’m pretty confident you don’t want to miss that because you have a hundred thousand words to compose before the end of next month. I know ‘being a writer’ sounds like a blissful life, but there are a lot of hard times too, especially when you’re exhausted and running dry but the deadline’s still charging toward you.

    Good luck, whatever you decide.

  43. Mark says:

    Hey Trent,
    Follow your passion – take the leap – there would be many opportunities which you could capitalize with more time. You already have a reasonably huge emergency fund to take the leap.
    All the best

  44. Mike Berry says:

    Here’s my two cents: See how much you can earn writing PART-TIME for a year. Cut back on this blog and go after more paying gigs. If you’re making a significant freelance income 12 months from now, move to full-time.

    Let me tell you, though, full-time freelancing is a grind. If you don’t enjoy constantly hustling for new work, it gets old real fast.

    You certainly have talent and drive. But I don’t think you’re at the all-or-nothing point yet.

  45. Clyde Williams says:

    Speaking as a part-time freelancer who can’t afford to make the leap, vh gives good advice.

    First, what you need to do is talk to professionals in that industry and ask for advice, or at the very least, get some idea of what being professionalized in publishing entails. It’s a totally different world, and there’s a reason not many bloggers can make the shift. Many people have a vague notion of making a living writing without ever having seen a writer’s paycheck. Writing made less than 15% of my income last year, and I put out 20,000 words or so.

    In other words:
    -have you seen a sample query for a magazine article, or a sample book proposal? Or successful ones?
    -have you seen a sample book contract?
    -have you done market research, and compared your story (which isn’t that unusual) with those of other financial writers? How would you make your work stand out?
    -do you have an idea of how hard it is to get an agent, or how to do that when most don’t read unsolicited manuscripts?
    -are you willing to relocate to NYC? Magazine and book publishing are centered there, and are competitive enough that they don’t need to dip into the rest of the country to find stuff to publish.
    -Have you studied other bloggers who have made the leap, who did not have previous industry experience? Julie on Julia is one of the best examples– she had a killer concept, a specific, book-buying audience, writes beautiful, funny, engaging prose, was based in Queens, and went to one of the top colleges in the US, so I suspect she had some connections who could show her how to do it.
    -Finally, do you hate your job so that quitting it will give you enough “go” energy that you can weather all the crap writers have to endure until you become a financial writer so beloved he spends however many years you have left until retirement on the best-seller list?

    The Simple Dollar is a good brand, but perhaps making that leap is premature if you’re not already making your living from it. One of the reasons I read your site is because your reviews double as Cliff’s Notes, frankly, so I not only don’t have to read the books, I don’t even have to go to the library; and because you boldface your main points, so I can skim your rather verbose articles. I would say you have some work to do before an editor will take you seriously.

    Finally, if this advice stings– which I have meant it to– I would recommend against making the leap now, because you’ll get worse from your editors, and perhaps the market, if you get a nibble at all. You are smart, but your financial writing shows you to be quite conservative. If you’re too old for the starving writer lifestyle, maybe it’s best to wait.

  46. Margaret says:

    Curious as to how this move would affect your feelings about having your SIL live with you.

  47. Peter says:

    If you go part time with your projects, you’ll have to cut back on the blog, which affects it and it’s voice and could hurt it.

    If you go full time, you may not make enough, even with a contract on the book, to pay for what you’re potentially losing, for many years. This could set you back a bit.

    But burning the candles at both ends hurts all of it.

    You’ve made a lot of changes in your life recently, e.g. new financial perspective, new house, new kids, growing blog. While there is certainly nothing wrong with change, you need to be carefull you’re not building so much momentum that you’re not able to catch your breath. Recommend considering the speed of change versus striking while the iron is hot.

    You also run the risk of resentment from your wife, and you’ll need to make sure that’s part of your discussion with her. She may resent the fact that you’re actually able to spend more time with the kids than she can. In a blog you put out what, a month ago, she was the one planning on staying home. Now it’s you. Sounds petty, but if you don’t raise the concern, it could happen before either of you recognize it as the root of other issues which could crop up.

    I’ve friends who have published fiction books and thought their careers were starting, only to have their next works fizzle out and remain unsold. Others hang onto the midlists, but can’t seem to get that big break. I don’t know how the non fiction world works, but if its as tough as the fiction world, well, good luck.

    However, to add some additional perpective to the doom and gloom, to me, this is really no different than when my wife wanted to stay at home with the kids and work part time. If this benefits the kids, and you feel you can reconnect with the job once they’re in school full time, I don’t see a major issue. You’d have done it for your wife. Why can’t it be you?

  48. Matt says:

    As a professional cook I am weary of your cooking blog. I know I’m in a different league than most people, but whenever you write about food I find many serious faults in your suggestions. Not that it’s a problem, I’m sure the food is delicious but I don’t want to read a blog about cooking written by a person who doesn’t have a very firm grasp on the concepts of cooking. I would like the frugal aspect however. My suggestion would be to find a job(paying or not) at THE best restaurant in your town, not the second best, not the one you like to eat at most, THE BEST. Nothing will teach you more about cooking more than having to make 200 dinners in a night. You could also take classes, but I would not recommend them. Trust me, I spent 4 years and a lot of money in culinary school and it is NOT worth it. Please feel free to contact me if you questions about cooking, etc.

    On another note have you considered a part time job, rather than a full time job? It would allow you to make some consistent income while providing you time to spend with your family and writing.

    I recently just quit my job when I was offered a position at an investment bank. The job ended up falling through but I took a part time job that I make enough money at to pay the rent and a few other bills each month. With the part time job and my emergency fund I can live 6 months without getting a full time job. Without the part time job I could go 1 to 2 months max. This provides me with plenty of time to properly search for a job that I want, which is not in the restaurant industry.

  49. Martha says:

    I am a part-time freelancer and my husband is a full-time freelancer, writing both fiction and non-fiction. He has published over 100 books (seriously). With major publishers. He makes $20,000 a year. There’s a reason most writers make their living teaching for writing programs and writing conferences. He worked his way up the way nearly all freelancers do: he worked a day job, in his case at a TV station, until he was selling enough writing to keep him afloat. What I see happening all the time is people quitting their jobs to write, and then they think they’ll start making enough money to keep them going. But you need a lot of work in the pipeline to produce steady money, and a considerable track record. If you’re making around $15,000 a year from your writing and you have several contracts already signed for the future, then I think freelancing might be a viable option. Until then, it’s just an unpaid vacation from the job which, I’m sad to say, will almost certainly end with getting another day job. Of course the mark of a professional is reseaching things ahead of time. You might consult one of the books on the business aspects of freelancing. Sorry to be so pessimistic. I don’t think your dream is impossible at all, I just think the timing right now might be a little premature.

  50. John Belt says:

    Here is my advice for what it’s worth. I am a boiler engineer by profession. However, I have tried several times to go out on my own, not unlike what you are pondering.

    I’ve tried a constrcution business, an online business, an MLM, real estate agent, flipping homes as well as others. Most of them were spectacular failures, a few did okay but weren’t lucrative enough to continue.

    I am now happily working as a boiler engineer, and will probably do so for the rest of my working career. I do not regret a single attempt at running my own business (except maybe the MLM). Each one was a worthwhile effort and a true learning experience. If I had not taken those chances I would have regretted the missed opportunities. Sometimes in life, one must try to grab the brass ring, even if destined for failure, just to know that you have the nerve to try.

    “You gain strength, courage and confidence by every experience in which you really stop to look fear in the face. You are able to say to yourself, ‘I have lived through this horror. I can take the next thing that comes along.’ You must do the thing you think you cannot do.”
    Eleanor Roosevelt (1884 – 1962)

  51. Sandy says:

    I sense very strongly that you are extremely driven and organized. You already do what seems like the impossible with work, family and side businesses, that I’m sure you could make writing full-time work. There are so many networks out there to help, too. Sometimes you have to go with your gut and not your head. This may be one of those times. Best of luck to you.

    By the way, can’t wait for the cooking blog! :)

  52. Lynn says:

    Best wishes on whatever path you choose.

    For what it’s worth, I think your writing style is interesting, easy to read and concise. I enjoy it very much.

  53. PJA says:

    “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly; who errs and comes short again and again; because there is not effort without error and shortcomings; but who does actually strive to do the deed; who knows the great enthusiasm, the great devotion, who spends himself in a worthy cause, who at the best knows in the end the triumph of high achievement and who at the worst, if he fails, at least he fails while daring greatly. So that his place shall never be with those cold and timid souls who know neither victory nor defeat.”

    Theodore Roosevelt

  54. Kim says:

    I think you should do it Trent. In previous posts you have mentioned that you could live in your wife’s income. You have your sister in law moving in. Ask her for a modest rent or child care as part of her living arrangement. I know that you have a LARGE emergency fund. Part time or consulting work could pick up some of the slack if things get tight. When you make this final choice, don’t just crunch numbers. Imagine yourself forty or fifty years down the road reviewing your life. Do you want to be telling your grandchildren how you could have been a great writer, but you never took the chance? I know, even if I failed, I would rather have the satisfaction of having tried. Trent, you never know what tomorrow will bring. We all assume that our time on this earth is long. You are lucky to have such a well defined dream. It would be a shame if you lived your whole life doing the safe thing and never got to experience your dream. Take the leap of faith Trent!

  55. Kim says:

    Ignore the chef’s advice Trent. I prefer to read cooking blogs by people who are just like me in the kitchen. A significant portion of TSD readership would read the cooking blog too! It would generate a lot of ad revenue, too!

  56. Greg Porto says:

    4 Good Reasons You Should Become A Writer:

    1. You have the gift of being able to communicate with people of all types. You speak to people about very important, difficult issues in a straightforward, respectful and effective way.

    2. You are riding an enormous market trend. You have the significant initial market feedback from your website. The job market and financial decision making process is only getting more complicated, this will not change. You have retiring baby boomers and a trend to entrepreneurship that only increases the need for the advice you provide.

    3. You are passionate about what you do. It comes through in everything you write. Passion is required for success – you have found an outlet for your passion.

    4. You and your family will always find a way to reach your goals. You are resourcesful and practical, in addition to being ambitious. You are highly unlikely to ‘drive the car off the cliff’!

  57. sp says:

    You have mentioned that you are a “planner,” and you should take that into consideration when making your decision. Keep in mind that having an irregular income will make financial planning more of a challenge, which would require extra time and may create a lot of second-guessing. Would this distract you from your writing?

    I am a planner, too. While my full-time job takes up a chunk of my week, I am able to have a savings/spending plan that does not require a lot of time to execute, I have full insurance coverage, and I do not lose any sleep wondering how I will cover all the bills.

    Pay attention to the source when you are doing research. People are all different, with different comfort zones, and what works well for one type of person may not work well for a planner.

    Planners are more careful, but we have dreams, too! There may be many paths to reaching that dream, but we all have to choose the path that is the right one for us.

  58. Wow, that’s a really tough choice. The fact that you can even consider it though is a good sign that your writing will lead to success.

    At some point I think you need to make the plunge and go for it. It’s not like you would be unemployable again in the ‘real world’. If it makes you feel better, maybe just try to ramp up your blogging income (or other writing projects) before you quit the day job.

    Don’t you think you’d regret it if you never give it a shot?

  59. Selena says:

    I’ve been a SAHP for about 3 years now and recently went back to work part time. The only aspect you don’t seem to be considering is social. If you are like my husband and can go for a week without seeing other adults then all is well. Personally I missed the daily face to face interaction with other adults. Just something else to add to your list of considerations. Good luck whatever you decide to do.

  60. barbara lochner says:

    I agree with vh! Years ago I co-authored a book that came out in hard cover & went to paperback. A chapter of the book was printed in Cosmo. Several other glossy mags printed sections and gave great reviews. My co-author and I went on tour. We did book signings. We were on national television and radio. It was optioned for tv and/or the movies. It ate up about two years of our lives.

    After the dust settled, we netted about $10,000 each. The IRS called me in for an audit because my expenses were so much greater than my income.

    My point is – I compulsively have to spell it out – you can be a very successful published writer and still earn zippo.

    My advise is the same advise as my tennis instructor. Play to your strong side. Stay with what’s working and figure out how to make money from that. Get some ads going or put together a book that can be down-loaded, etc. Other web sites have inched into money-making and you can, too.

    And, of course, good luck regardless of what you decide to do.

  61. Mary Hunt says:

    Trent … I have been a full-time writer for the past 16 years.

    I have a subscription website with 30,000 paying members, write a daily syndicated column for Creators, have 17 published books, have 66,000 opted in on my daily email list, a contract with a major woman’s magazine as a regular contributor, an active blog and I travel and speak quite a bit.

    I can tell you it’s the equivalent of working 2 or 3 full-time jobs with part-time takehome pay. Writing does not promise a slam-duck income. The struggle is getting paid for what you write and in a way that you can depend on that income.

    I suggest you not leave your current job, AND at the same pursue writing full time to test the waters. See if you can land a book deal (you won’t get rich off that but it will give you a great jumpstart). That will give you a taste for the schedule, the pressure and the deadlines.

    If you think you are burning the candle at both ends now, leaving your job to pursue writing full time will require burning that candle at both ends and in the middle too.

    By the way … I could have never done this while our boys were still at home and lived to tell abouut it. For the first three years I retained my job as a full-time real estate broker and plowed every dime from writing back into my writing biz which now employs a staff of 10.

    Whatever you decide … good luck. By the way, three years ago my husband and I founded a mainstreem book publishing business. We’d love to see your proposal.

  62. kath says:

    I say go for it. You only live once, and you don’t want to end up a bitter old man, being resentful about the chances you didn’t take in life. We all know people like that. Don’t be one of them. If everyone waited until all the planets were in complete alignment to follow their dreams, no one would have children, businesses would not be started, changes would never be made in the world. Think of all the people who started out in life with nothing but a dream and went on to do amazing things. They took a chance. You seem to have a pretty realistic picture of what life will be like if you do this, and you’ve definitely been thinking this through. My husband was laid off from a job a week before our third child was born and decided at that moment to start a business, with no plan and terribly underfunded, with a stay at home wife, but we survived and thrived (22 years later and owning a business in a totally unrelated industry than the one we started in), because we were smart about it. If one thing wasn’t working, we tried something else. We keep up on the newest techniques, products and marketing. We made the necessary sacrifices, and try to keep abreast of where our market is going. You are smart and ambitious. You’ll do well. You probably won’t get rich quickly- most people don’t right away, but you seem to already realize that, and are willing to accomodate it. If you are too nervous about it, then I agree with the posters who mentioned trying to take an unpaid leave of absence from your job. Maybe this experience will lead to something better. Maybe you will find that writing isn’t a career you want to stay with, but maybe it will open the door to something even better. You already have one income coming into the house with your wife’s job, that’s a plus, and you’re realistic enough to know that if this is plan is not working, then you have to change it. You also have youth on your side. It’s easier to try and fail now than it will be when you’re 50.
    Go for it!

  63. Mary Hunt says:

    Please correct my spelling … “mainstreem?” Yikes

  64. This is definitely a challenging decision to have to face. I tend to be a planner as well, and what I’ve done throughout my life has reflected that. I’ve put many things on hold in order to achieve milestones in my life at the pace and point I’ve felt comfortable with. I planned when I got married, when I had kids, and when I’d make that first million.

    Anyway, given all that I can only share with you what I would do. It sounds like you are currently enjoying yourself and things are stable as it is. I’d stay status quo for a bit longer (maybe make a serious dent on those debts), but that’s just me. Either way, when you’re truly ready to jump off the cliff, you’ll know.

    I find that there’s always a time for everything and in my experience, it has always become apparent when I should be doing something — and by heeding that intuition, we’ve managed to have things work out pretty well.

    Good luck with your decision, Trent. I’ll be one of those first in line to get your book. I *truly* look forward to that time.

  65. Katy says:


    Yes, you DO have a story worth telling. Having said that, don’t limit yourself to making your decision by the end of Thanksgiving weekend. Please. Do the best you can, in small bites that will ad up if you have to. I am of course hoping you will be able to do it – but don’t give up. You don’t know what’s up ahead and you have the gift of TIME. Meaning You’re young. Sending the Best thoughts and hopes to you.

  66. Sandy says:

    If I were you, I would take the advice from a horse’s mouth, i.e. vh above. Normally I would encourage anyone to go for it, whatever their passion, but writing, unlike most other “small businesses” just don’t command the annual salary that one with dependents would need over time.

  67. Heather says:

    Trent: You need a vacation. Think only about getting rid of the parts of your current gig that you do not like. You are a wonderful writer by the way.

  68. jan says:

    Ask yourself two questions, “What’s the worst that could happen?” “Can I live with it?”

  69. Sandy says:

    Pray. Find where God leads you. And if there is a shard of feeling that you should do it…jump. Do it. Don’t live with regrets that you didn’t try. When you work for someone you are limited by their vision. When you work for yourself, you are limited by only *your* vision.

    I know of what I speak. If you can, and feel led, do it.

  70. Rob in Madrid says:

    This is one time where logic will always fail you, no matter what you look at it logic will always to take the safe. I’ve had loads of friends who haven’t had near the financial resourses that you’ve had and didn’t think anything of quiting and “following thier dreams. thinking of one person who left a very good job with top notch benefits to pursue his dream of running a business, 5 years and 3 failed business, a lost house, a bankrucpy he only went back to work at a real job under the threat of divorce (and it keeps him there too, wife said if you quit stop by the lawyer first) They also had kid 3 and 4 during that time and she has never worked. Yet they survived.

    Emotion will always trump logic and none of our friends ever wound up on the street and I don’t you will either if you quit. And unlike most people you have the resources to last, non of our friends did.

  71. Katie says:

    My two cents about this whole situation:
    1. Your story is not unique. A lot of people mire themselves in debt and then manage to rescue themselves pretty quickly. Reading even a handful of personal finance blogs will show you plenty of people who have gone through the exact same thing you have. Any book you wrote about it would flop because you lack the name recognition, the advanced degrees, and the compellingness necessary for a good seller.
    2. Your readership is very small. I live in a small town, and our population greatly exceeds your readership and feedership. Besides, do you think all those subscribers actually read your blog every day? Doubt it. Until your readership exceeds the population of your home county, you don’t have anything to boast about.
    3. I agree with the disgruntled chef above about your idea for a cooking blog. For one thing, the recipe market is overly saturated, and plenty of people know enough about cooking not to need a full pictorial for every recipe. Also, are you supposed to set your computer on the kitchen counter so you can follow along with the handy pictures so you know what bread dough is supposed to look like?
    4. There are people who know a lot about the writing/publishing biz. LISTEN TO THEM. Publishing is a hard field to get into. A friend of mine with plenty of connections and a lot more talent than you have wrote and shelved four complete manuscripts before her agent was able to get her a publishing deal on the fifth one. With all the time it took her to write and edit the book, she guesses she averaged about $2.20/working hour (and this is only on the book that sold, the others had no return on her time investment). And she still has to go to writers conferences and workshops and signings and meet and greets, and she gets to pay for almost all of it out of pocket, since it’s part of her publishing contract. As a Midwestern author, expect to have to self-fund plenty of trips to Chicago or St Louis or Minneapolis, and should you happen to write children’s books, you’ll be going to elementary schools until your head explodes. Also, expect those investments not to pay off in the form of increased book sales or having a bigger publishing house offer you a contract. Big houses won’t put their money on the line unless they’re pretty sure you’ll be a best-seller. As an unknown from Iowa with no pre-existing fame or a profitable and proven readership, I can tell you that they’re not going to take the plunge with you, no matter what you write.

    Lastly, if you can’t take all of the above criticism without batting an eye, you don’t have the guts for the publishing business.

  72. Andre Kibbe says:

    One option I haven’t seen mentioned is maintaining your day job and reducing your posting frequency (against my own self-interest, of course) on TSD. Tim Ferriss argued that prolific posting is counterproductive, since a potentially high-traffic posts can get buried by subsequent posts before being Digged; it can take a couple of days for it to propagate through the blogosphere. You might be creating unnecessary work for yourself by posting 3-4 times a day. Once a day might be a lot less stressful while paradoxically increasing your traffic as each post has more time to accrue links and commentary. Good luck, whatever you decide!

  73. Kathryn says:

    You’ve gotten lots of advice…but I don’t think I saw this mentioned yet: Staying home to take care of your children is a full-time job. Very few people can combine serious hours of work with caring for the kids…and if you continue to pay for day care, then you won’t be saving enough money to offset the loss of your current income. At least, that was my experience. I did the at-home free-lance work (more editing, transcription, desktop publishing, etc.) for two years with my first baby. There just wasn’t enough time to do both well. And as the kids get older, they take more time, not less.

    If you want to cut back on work FOR THE PURPOSE of staying home with your kids…great! More power to you. But if you think that you can take care of your kids while working a full-time writing career…well…

    If you really want to launch a writing career…I vote for leaving the kids in day care and finding a part-time situation to allow you more time to pursue the writing.

    Good luck to you.

    – K.

  74. mamamardee says:

    being someone who chose to stay at home with our children, i can somewhat understand your desire to be there while your little ones grow. it is a choice i will never regret! we decided before our children were born that if we adjusted to one income we could make it. we would not be working to pay for the “toys” and our children would have a parent to guide them. you and your spouse are the only ones who can make this decision. no one else can understand what it will take or what it will mean. i believe you can do this and remain happy and financially fit. best of luck

  75. Dean says:

    My we ALL love to give advice, don’t we—-a comment on human nature, not a sarcastic put-down. In all of your writing My response was to tink and feel,”What a beautiful guy. I’d give my eyeteeth, if not my eyes, to be his friend. Your writings have all spoken to the fact that money is interesting, but not primary. Look over your past writings, I say, and you have already answered your own question. My very best wishes, Truly, to you.

  76. LC says:

    Don’t listen to the chef. I also appreciate “real life/everyday foods” in the kitchen and I reall like the instructional style that you have. I think that you have a gift for writing things (about cooking and personal finance) in a way that is really relevant. I have tried the recipes that you give here and I enjoy them far more than any “professional” recipe that I have read.

    I think you should go for it. The people who say that you need to have a publishers contract in hand (or work in a great restaraunt) before you quit may not understand that you aren’t depending on this income for your entire livlihood, but the primary driver is to pursue your passions.

    I agree that you should consider the worst case. Let’s say, god forbid, that you quit and find that your writing turns up few profits and your wife loses her job. What would happen? If you believe what you wrote in “Ten Steps to Financial Success for a Minimum Wage Earner” (I do!), you would realize that you would still be able to put food on the table and stay out of debt and save for the future.

    I believe that you will be rewarded for following your heart as long as it makes sense, which is the case here.

  77. Gloria says:


    I would love to see a cooking blog by you and truly hope that you keep up your daily blog for the Simple Dollar. Best of luck to you whatever you decide just don’t stop your current work.

  78. Imelda says:

    One thing you have going for you, Trent, is your discipline. The way you get so much done and never fall behind on your blog is impressive, and, I imagine, will stand you well as a freelance writer.

    I do hope you listen to some of the comments from current freelancers, though. They’re the ones you should be talking to, rather than folks like J.D. who share your perspective.

    On another note, add my vote to those who say you should ignore what Matt the chef wrote! Why on EARTH would you take a job at a restaurant to teach people how to cook for themselves or their families? Why would you need to know how to serve 200 meals a night??

    Last comment: I don’t know anything about your wife, or about your marriage. But I do know that A LOT of women resent being the main breadwinner while their husbands stay at home with the kids. I really hope you find a way to avoid the tension this adds before you make the leap.

    In any case, best of luck.

  79. JReed says:

    Isn’t it funny…the further we are from the edge, the more afraid we become of the edge. I can remember having no money to speak of and not even thinking about it. I just did what I wanted to do and fiqured out how to make it work as I went along. Now, with savings in the bank and no mortgage, I agonize over every life decision? I guess its because there is more to lose? My dad always said “If you don’t go for broke a few times, you’re not living”.

  80. Ericka says:

    ” I’m afraid of burn out and regret.”

    You can always go back to even a part time job if you feel burnt out or for whatever reason your writing doesn’t bring enough to cover the bills. A friend of mine quit her job to work full time on her website (www.aswearemagazine.com), and is now looking for something outside home again. It’s not a do or die situation… there’s lots of room for cushion. :)

    Good luck!! My dream is to be able to drop back to part time at my “day job” and have my photography be a stream of income. One day… one day… ! :)

  81. yvonne says:

    Trent what you do is awesome!! More of anything you do would be worth paying for. That from the cheapest person you will meet.
    I remember a quote that I heard along time ago when making hard decisions. “F.E.A.R.” Is nothing more than “Fantasized Experiences Appearing Real”
    I wish you and your family the best.

  82. Teresa says:

    I know it as “False Evidence Appearing Real”
    It’s a good one!
    Trend, all the best! I love your blog.

  83. JT says:


    I stumbled onto your blog a few weeks ago and find myself coming back regularly. Its easy to see why its popular – your writing style is unpretentious and honest. You pick topics that are relevant and relatable to most middle class people who are trying to juggle saving for the future with our everyday lives and expenses. I think you ultimately have a future as a writer, but I would offer the following advice:
    1. You need to build up a much bigger emergency reserve since your wife will now have the sole STEADY source of income, shoot for 12 months living expenses.
    2. The ideal solution, as others have mentioned, would be for you to arrange part-time or job sharing with your current employer, but that may not be possible and it doesn’t reduce your day care expenses.
    3. I don’t believe your day care expenses will fully disappear as you are assuming…you may still need to meet with clients/editors/business partners during the day, and will need to think through child care for these times.
    4. What is your fall-back plan for if this doesn’t work, or your family situation changes and requires you to earn more income (e.g. your wife loses her job, or is medically unable to work)? Can you to return to work in your field? Plan to maintain as many work contacts as possible to facilitate this if it becomes necessary.
    5. Can you supplement your writing with other work that is related? For example, H&R Block and others hires tons of seasonal tax preparers for Q1 of each year. This could be one way to supplement. Or, community colleges will often post for adjunct faculty spots that pay per class – you could teach on personal finance, or other areas that you meet the qualifications for. Or ask your local community center if they need instructors to teach various enrichment classes (cooking, personal finance, etc)…this could also help you promote your other activities.

    Anyway, those are my thoughts. I hope you do decide to give it a go, just think through it from all angles so you don’t compromise yours or your family’s financial future in the process.

    Good luck, and thanks for the great blog site.

  84. victory says:

    Trent my brother via frugality,

    Go for it! I just moved from East Africa to Vancouver, Canada for the simple reason that there are many opportunities in this part of the world. Things have been a little rocky but they are easing up now, due to God’s grace and faith in God. I strongly believe that all things are possible.

    Take a step of faith and everything will be okay. Get out of the comfort zone and the paralysis of analysis. Trust in God and all will be okay.


  85. Sam says:

    Wow, alot of people have a great deal of respect for you and your writing talents. Why not finish that book you’re thinking of and see where it takes you?

  86. viv says:

    Well, good for you! You have a lot of choices and a lot of talents. I don’t profess to have the answer as I don’t know enough about you or your situation. I do know that the question I always ask myself when faced with a major decision in life (and it always works) is: down the road, will I regret doing or not doing this? No regrets!

  87. Dana says:

    Trent, I currently am struggling with the same decision. I do technical writing and freelance editing, but I’d love to concentrate on fiction.

    Please keep in mind that there will always, always be people who will criticize your writing. Best-selling authors have their work trashed all the time. Joe Schmoe from Arkansas telling you your writing “sucks” doesn’t negate the millions of hits you’re getting on this site.

    The people I know who have successfully transitioned to freelance writing have followed this rule: don’t quit your regular job until you’re already comfortably replacing your income. It will be a struggle to balance your time, but if you can show yourself that you can make a living this way, the confidence boost will accelerate your success when you do take the plunge.

    Best of luck.

  88. Linda says:

    I was first linked to your blog entry about bread making by a friend and I have been subscribed to your blog since then. You mention an idea for starting an instruction-oriented cooking blog here. From a purely selfish standpoint, I just wanted to let you know that I would love to see it!

    I thoroughly enjoy reading your Simple Dollar blog because your advice is so straightforward, organized, easy to read, and genuinely helpful! If your cooking blog is anything like that, I will be ecstatic, as will my tummy. We’ve already tried your advice about bread, and it has reminded us how fun making things in the kitchen together can be. Thanks, and good luck with whichever Major Life Decision you choose.

  89. Caeli says:

    I see many comments here that are well thought out. However, many others seem to have commented before actually reading the post. I even see some people asking if you thought of part time or the cost of child care as though you didn’t already address these issues. My point is, it’s annoying. If you are going to share your opinion at least read the post, people.

    I think your best bet is to pay close attention to the advice of people who have been there. There are lots of good comments from people in the publishing industry. Give those comments precedence. It’s true that you should follow your dreams and spend as much time as you can at home while your children are young. It’s also true that you shouldn’t risk the stability of your family while your children are young. From experience, living in a storage unit with electricity for a few years does a lot more damage to a young psyche than living in a real house with parents who don’t have time for you does. Yes, time is short. But you are still young. You have at least a year to stockpile savings and consider the decision from every angle, network inside of the industry and prepare for the shift. Take your time to ensure your success the first time around, not the fifth.

    I also seriously disagree with the criticism of the cooking blog idea. Plenty of people do not know how to cook from scratch. In fact, I would say the people who are able to make their own bread and do so on a regular basis are the exception rather than the rule. Especially people in their early twenties like me. I don’t have anyone to tell me whether I can still make that muffin recipe even if I don’t have baking powder. No one ever told me what baking powder is or does. I had to do quite a bit of digging online to find out that my muffins would be cookies instead if I did that. And that was not just a quick search, either. I think you would be filling a serious need and I would subscribe to it immediately.

  90. Ro says:

    I think just about every point that could be made either way has been made! Let me just add that I think you are a very good writer and I enjoy your blog. I’m also a very bad cook so I would read your cooking blog if it becomes a reality. I think you should take a while to think this through though and examine all the possibilities. Good luck to you as you figure this out.

  91. Shelli says:

    Please consider: If you’re burning out writing multiple entries on a blog, on your own timetable, with your own editorial standards, do you think it’s going to get easier as a freelance writer whose copy will have to live up to higher, sometimes arbitrary standards?

    Don’t try to decide this weekend. There’s no reason you can’t wait six months. Use that time to get to know the field. Publishing is one of the most hotly competitive markets in the world. What do you have to offer? How can you get it noticed by publishing houses? And if you do, will it sell?

    You have time. Learn.

  92. Stephan F- says:

    I am thinking about making major changes in my life and there are a lot of signals that I have been getting that it is a good idea but overcoming my own fear and those of my family is the hard part as well as making some kind of plan to pull it off.
    Thanks for the template.

  93. Trent,

    Good luck in your soul searching as that is where you key to your problem is. Basically as I see it you could either:

    a) Do it and write more and take all the risks that go with it. If you do this get a huge income stabilization fund build up to help the swings in income (6 to 12 months worth). Also remove most of your debts.

    b) Don’t do it and write less. Really I like your work, but your producing more than you need. I actually skip about half your posts because I don’t have the time to read that much.

    Best of luck and remember to be honest with yourself.


  94. Irene says:

    I spent the best part of my life wanting to be a writer. I listed all the reasons why it wouldn’t work. But I felt the real stumbling block for me was the lack of a formal education. I mistakenly thought I needed one. By the time I realised that no one can teach you to write, that its a talent you’re born with I had reached my fifties. One day I woke up and thought, what have I got to loose? I wrote my first comedy play. It was a massive hit both critically and commercially. I have gone on to write a number of other plays, as well as being commissioned by various organisation to write issue led plays. Don’t wait as long as I did to follow your dream. Go for it, and good luck.

  95. Leah says:


    Can you stay at your current employer part time? Would they be willing to take you back if you left and wanted to come back?

    As a part time worker and spouse of self employed artist, I’ve struggled with the benefits issue for years. Not fun, but can be managed.

    Best of luck on your decision. Don’t doubt your writing–it’s incredibly readable and clear. You explain the inexplicable to folks like me who have no mind for finances. I’ve appreciated your words…

  96. Sue says:

    Some thoughts on the book publishing industry might be helpful in terms of strategy and income:


  97. Susan says:

    I left a miserable job in advertising to work in travel writing and so far it’s working. I don’t have kids, but I have a very high rent living in NY, an luckily I have a husband who is emotionally and financially supportive. Sometimes you can’t plan out every detail of how everything will work. Don’t you think you’d be a more passionate person, a better Dad, a better husband, an inspired human being if you took a leap of faith and did something that works for you? With over a million subscribers, you can work on selling ebooks or seeking out ads and affiliate programs that match your philosophies and principles.

    Sometimes I make out a ‘worst case scenario plan’. And these plans always end up being fun. If money starts getting tight, what can I do? It sounds like you could teach a cooking class, host a tele-class or seminar, teach online or at a local community college about finances, do more consulting, the list goes on. I once transcribed dozens of interviews between a grad student and aspiring pro wrestlers. It was fun, lucrative, informative, and I made a great friend.

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