Piecing Through A Major Life Decision

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

T
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.