Updated on 05.07.10

Seven Easy Steps to Your Dream Job

Trent Hamm

A few days ago, I was reading an article in ESPN Magazine (I started getting a subscription to it a while back after I signed up to play fantasy baseball at ESPN.com) by Vivian Chum that talked about what you would need to do to get a job as an NFL coach (you can read the article online if you’re a subscriber). After reading the article and letting it ruminate in my mind for a while, I began to realize that the article actually had pretty good advice for any “dream job” a person might have. In fact, I used most of the advice in the article on my own path to becoming a full-time writer (a “dream job” for me that seemed totally unrealistic five years ago).

The ESPN article had six tips, but while thinking about them and remixing them a bit, I stretched them into seven distinct steps. Here they are, along with my own application of them while moving from office work to a stay-at-home writer and dad.

1. Work for free.
Internships. Taking on projects without pay. Volunteer work. What do these all have in common? They’re great ways to gain experience in competitive fields, but you’re trading pay for a deeper level of experience than you might get otherwise. Almost every field under the sun has some avenue to build experience through internships and volunteerism, from coaching and computer programming to office work and trades. Such situations allow you to gain incredibly valuable experience, the kind of experience that will launch you into real work in that field.

Of course, you’ll need to put food on the table while doing this, so I usually suggest working at another job first and saving every possible dime so you can live off of your savings while doing the internship or volunteer job.

As a writer, “working for free” largely meant blogging, especially at first when I didn’t have many readers. I spent a lot of time writing articles for The Simple Dollar (and for earlier blogs of mine, including a parenting blog) and not earning anything from them aside for perhaps enough pocket change to buy a cup of coffee. I kept plugging away. What happened? I became a better writer. I learned what my audience wanted to read. And, gradually, readers started coming.

2. Have some unusual resume elements.
What experiences or knowledge can you bring to the table that differentiates you from the others? You’d be surprised how often something “outside of the box” can get the attention of others, even if some of the other candidates have better “ordinary” resumes. This often goes hand-in-hand with the internship/volunteer suggestion above – if you’re plying your trade in an unusual and challenging situation, you’re going to immediately win some respect from potential employers or clients.

Always seek out the unusual and challenging in your life experiences, whether directly tied to your dreams or not. Such life experiences build both character and adaptability, which are invaluable at almost any career.

What did I do that was unusual? In terms of the obvious, I think I did two things differently. First, I openly admit that I flunked (badly) the early personal finance tests in my life (and still fail some) and, second and more importantly, I was willing to admit that while also writing about personal finance. I have never, ever tried to create a sense that I am some sort of personal finance guru or expert. That’s different, and I think that’s why the most popular personal finance blogs have succeeded – they’re not afraid to admit failure in a field where everyone seems to constantly talk about the “big win” and how much money they’re making.

3. Keep those unusual elements to yourself.
You don’t need to go around bragging about your great experiences. Keep them quiet and under the vest and just let your walking do the talking. You’re almost always better off to understate what you’ve experienced and what your skills are than to brag about them or overstate them. Yes, bring them out when you’re shipping a resume, but don’t bring them up when you’re working. Keep them in your back pocket until you can bring those great elements to actual use.

It’s a lot more impressive (and demand-creating) if you can slap together a computer network quickly out of whatever equipment is lying around out of the blue than if you spend some time each week bragging about how you set up networking in an African village.

There are some elements of my own life that I don’t discuss that somewhat shape my perspective on here and make it “unique” in some ways. I occasionally mention them, but I don’t use them as a red badge of courage. I don’t need to. The end result is that when such an issue comes up and I do actaully mention some of those issues, it makes much more of an impact. Here’s an example of this, when I talked about the deep value of $4 prescriptions for me personally.

4. Ask your biggest doubter to be your mentor.
The person you should be asking for help and for mentoring is the person whose skill set is far beyond yours. Tell that person flat-out that you are woefully inexperienced, but that you want to learn from them because of the respect you have for their work. Ask them what it takes to make it.

There’s no reason not to swing for the fences here. It’s only rarely that a person gets a sincere face-to-face request to be a mentor from a person humble enough to admit their faults but ambitious enough to actually ask for help and smart enough to actually seek that help. The traits of a person willing to do this are the traits that most people recognize as ones needed for success in any field.

I’ve had three major mentors in my life. When I first met each of them, I was barely on their radar screen. Each time, I found an opportunity to talk with them, explain where I was, explain the respect I had for their work, and simply ask for help. Each time, they happily offered it, for my own benefit. What did they get in return? There are three people out there who will always have my help if they ask for it, period.

5. Learn some tricks, practice them, and keep them to yourself.
Every career path has skills and tactics that are the basis for impressive work. It can be anything from incredibly fast collation or some great programming or writing techniques to mad skills with Photoshop or playing the piano.

Even some skills that aren’t necessarily related to one’s career path can be a huge virtue, as they can often be the tie-breaker between similar candidates. Which candidate would you hire – the ordinary one or the one who is such a good piano player that they’ve made money doing it in their past?

Learning such skills teaches you discipline and patience. Even better, these skills can often burst out at incredibly fortunate times – I witnessed someone open up to a colleague due to a piano duet before.

The more skills and tricks you have – particularly well-practiced ones you can pick up at any time – the better off you are.

My “secret skills” include some strong programming experience and the ability to write very good first drafts, which minimizes the amount of time I have to spend revising (at least for blog postings). My programming experience came from a previous career, while my solid first drafts came from my high school English teacher.

6. Be a nerd.
The more you enjoy obsessing about the minutiae of your work, the better off you’ll be in the long run. Revel in learning more about your work. Dig deep into the details, even the trivial ones. Hang out with other people who similarly love the details.

Great politicians (think Bill Clinton) obsess about politics and congregate with other political nerds. Great computer programmers (think Richard Stallman) obsess about programming and congregate with other programming nerds. The list goes on and on – the top people obsess over and practice the details and love congregating with other nerds about the same topic.

I love to read and write. I participate in a lot of different writer’s forums, particularly those that focus on a lot of the “nerd” details of writing. It’s not about just throwing down words on a page, after all. I often “practice” this nerdery by trying writing experiments and digging into specific skills (like better metaphors, etc.).

7. Read. Read more. Read even more.
Whatever you want to be doing, you should be reading about. Spend at least an hour reading about your topic of focus every day. Read technical books on your area. Read books that connect your area to others. Read books that round out your learning in other areas.

Read. Reading is learning. Reading makes you grow not only in your field, but as a person.

I read three books a week, minimum. One of them is usually related to The Simple Dollar. Once a month or so, I read a book strictly related to writing.

You can do this. It takes time and passion, but almost everyone on Earth can have a job they dream about if they’re willing to invest the time and make the sacrifices needed to get there. Just throwing your resume out there will just mean rejections – you have to go beyond that.

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  1. Trent,
    I can agree with all of your points. But, I do have an issue with #5. While it is nice to have an edge, I think it is always in the best interest of everyone to share best practices.
    Unless these are absolute trade secrets, I believe that we will be rewarded when we are able to help others improve.
    Just my $0.02.

  2. Srikanth says:

    I like this. You could actually call this “How to make _any_ job, your dream job”. Bookmarked.

  3. Jon says:


    Trent never said anything about best practices. He was referring to skill sets you gain that are outside of your career path. He is talking about extra skills that give you the edge in business or a position.
    If I am hiring 2 programmers with identical skill levels, and I happen to find out one is skilled in Photoshop or has submitted articles to a technical journal, that person will get the job, hands down. Those skills are outside the realm of pure “programming”, but are an added bonus to have as an asset.

  4. Robert says:

    This is just the kind of advice I needed. I am passionate about brewing beer but have no formal education. Only experience I have is home brewing for a few years. I have just begun to look for an internship and I’m hoping these tips will come in handy.

    Thanks Trent

  5. Ramiro says:

    Regarding working for free, that can be valuable most of the times, but not always. Volunteering can send the message that someone is willing to let you do the work, as long as they don’t have to pay you. You don’t want to send the message that you are an amateur. So thread with caution in regards to working for free. Just my humble opinion. The other points are right on!

  6. Sergiogsr says:

    I agree on having special and non common skills in your normal career environment (I’m a mechanical engineer, and having skills on Photoshop, programming, video editing and web development, give me the opportunity to get involved in special projects at my work place; this of course means a lot more experience and learning).

    But I dissagree on number 1:

    You wouldn’t never agree to work for free (on a more complex meaning that the economical), less if you really like the place and you want to be working there for a long period.

    What I mean is that, if you’re going to be working there without a monetary retribution, you need to make a clear statement about the tools you need, the activities you’re going to do, the time required, and some more. If you’re there looking for academic knowledge, ask if you can use the experience and the work you are doing in acadamic development (thesis work, reports and papers for universities or magazines), or in the example of programming if you can register the software you create (bigger companies, usually take all the credit, sell the program – even if software is not their base business – and give you nothing). NEVER WORK FOR FREE, if you don’t want money ask for experience in paper evidence and credit.

    Sometimes, when you leave and ask the company for recomendation, they forget you….even if they are still using your work.

    The same if you already are working with a $ retribution, and those extra skills means more work for you. Maybe your boss is not paying you extra, but at least ask for a defined time to do that “special skill related activity”.

    I’ve learned (the hard way) that you wouldn’t start working, as a “just out of school guy”, in the company of your dreams.

    Boss will get used that you like to work for almost nothing (because of your knowledge thirst) and that he’s doing you a favor by keeping you there. You will have more responsabilities, but money or recognition will not grow equal.

    Recommendation, work for cheap, learn a lot and move fast.

  7. @Jon
    In your example there is addedv alue because those skills are assets taht your company could likely use. ie: closely related to the occupation.
    What if thsoe extra skills were basket weaving or woodworking? Would it matter then? Likely not. Those assets aren’t of any value to your technology company.

  8. Jon says:


    Absolutely they still matter. Basket weaving and woodworking require planning, attention to detail and craftsmanship. Those skills easily transition into my technology company. Those extra skills also require time commitment and perseverance. Both of your examples also require dealing with mundane repetitive actions; also good skills in technology at times. These are all valuable assets regardless of the type of company. Never underestimate the hidden skills that an unrelated activity can bring.

  9. Jeremy - fasthabits.com says:

    I couldn’t agree more with the value of reading. There are so many benefits, you don’t even imagine until you start digging into books.

    I have recently become addicted to them, the more I read, the more my thirst for knowledge increases and those books enlighten me to even more books.

    In this new age we are coming upon, one of the few commodities we will be able to offer is our knowledge, and if you’re not reading you are not growing.

  10. Kat says:

    Having done interviews for multiple companies, when asking a question such as “how do you deal with such-and-such” being able to relate that to something you do not-for-work (“actually, I’m very adept at repetitive, detail-oriented tasks, as I am an avid basket weaver on weekends”) makes an impression and you are more likely to be remembered. Sometimes, that’s all you need, you may have the better experience, but if the interviewers can’t place you 2 days later among the others, you don’t have a chance.

  11. Great tips. As a newer blogger, I have to admit I’ve grossly underestimated the time commitment to writing.

    I read some of my earlier posts and saw posts that even a seventh grader could top…

    Since blogging, I do know that both my writing style and speech in general, has improved.

  12. Eric says:

    RMS…..? really? Really? He’s not been a good programmer since the day he decided soapboxing was more important than engineering.

  13. Debbie M says:

    Well, I like the ones about learning more [by doing–even if for free (#1), from a mentor (#4), by hanging with others who know this (#6) and by reading (#7)], but the others didn’t make much sense. Kat, your explanation helped.

    But I’ve often tried to get a job in a different field and found that having a bunch of related skills has never mattered. “Oh, yes, I see you’ve tutored middle schoolers, you’ve taught college students in the classroom, you’ve worked with classroom-sized groups of middle schoolers at summer camp, you’ve taught math to people in elementary school and college, you’ve scored math teacher certification tests, you’re certified yourself, you passed our weirdo standardized tests at 99%ile, but since you’ve never actually taught middle school math in the classroom, screw you.”

    It all depends on what they can find. My experience has been that if they can find someone who’s already done the exact same job, they will chose that person over someone who has not. I have only been able to get hired for jobs with very high turnover, where they have to hire a bunch of people at once, or which no one has done before (because it involves propriety or otherwise rare software). But then I’ve read that most people get jobs through contacts and none of my contacts know anything about fields that interest me.

    I want to add something to #6: you can often join professional organizations even if you are not yet in that profession. If you take a leadership position, you will get to know more people than if you are just an active member, and knowing people makes it more likely you will get job offers. You may think you shouldn’t take a leadership position if you are not even in the field, but there are plenty of positions where that doesn’t matter (treasurer, membership director, web presence, secretary, that sort of thing).

  14. Tom says:

    I think the title should really be Seven Simple Steps not Seven Easy Steps. Although they seem straight forward I doubt implementing all of them would be easy.

  15. t says:

    Great advice – I was suprised about the unrelated skills part – but what if you don’t know what your dream job is? I’m past 40 and I still do not have a clue what I want to do when I grow up. My interests and talents are varied and do not necessarily lend themselves to gainful employment. Now what?

  16. Elizabeth Howell says:

    It took me a long time to figure some of these steps out on my own, so I’m glad they’re outlined here. I now blog daily about my passion and only wish I would have done it sooner.

    Yes, it’s free work, but the rewards don’t need to be money to get satisfaction — it allows me to connect with a community, stretch my writing skills and learn about new things to in turn teach my audience.

    Thanks for posting.

  17. Alex says:

    Step #0: Find your dream job.

    I know plenty of people who would love to have a dream job, but if you ask them what they would do if they had a billion dollars, they say things like, “play video games” or “watch tv and read books” or something along the lines of “entertain myself for my own benefit.” If you’re one of those people who has just never seen anyone and said, “I would kill to have that job,” what do you do? How do you figure out what it is you want to do?

    My own best guesses have been to journal to find what you like to do, seek out different experiences through friends, do volunteer work that even slightly piques your interest. But I have a close friend whose found plenty of things that are fun to do for a little while, but who would hate to have to do them for a living.

  18. Skip Orem says:

    This post inspired me more than anything I’ve read in the few months. I’m now officially hooked on this blog. Thank you to the max!

  19. MP says:

    Sorry – work for free? That’s just a way for employers to cut costs and shortchange workers.

  20. Leah says:

    I agree with MP. I’ve worked for really cheap (internships), but I won’t work regularly for free. It’s one thing to volunteer somewhere on a 5 hour a week or so basis (that’s a good way to try out the waters and see if you even care for a field), but I don’t think it’s a sound practice to put in lots of hours somewhere for completely free. The only time I’d do that is if I got something concrete in return, like college credit or a big step up.

    Then again, that’s what you have to do in some fields. My brother works in the film industry, and he’s been busting his butt for the past 4 months working for free. He’s making good connections by working internships at 3 different places, and he’s gotten loads of good feedback from his bosses. I admire his drive, but that sort of dedication isn’t for me. I really hope he’s able to break into paid work soon, because I don’t know how long someone can go without some sort of paycheck.

  21. K.C. says:

    I learned my sales skills by working on straight commission. Direct sales commission jobs are easy to get. It’s a lot like working for free if you don’t make any sales! I figured it out before I starved, discovered that I enjoyed it, and continued to work on a commission basis for most of my thirty-five year career.

    Those outside interests and skills were indispensable as they helped me connect with prospects and customers on a non-business level.

  22. valleycat1 says:

    I don’t quite see how keeping your special skills to yourself gives you added value to a potential employer – how will they know you are the one with the tie-breaking skills if you’ve kept them to yourself?

    Actually, in my present job there are a number of people performing the same functions (I work for a county-wide organization). It amazes me that no one asks us to share how we accomplish the various tasks efficiently – as each of us have our own strengths and weeknesses. We do share on an informal basis at random, but the employer isn’t gleaning any info from us & we’re basically on our own to figure out processes on our own within the overall parameters.

    Otherwise, I’m proud to admit I’m a nerd about certain aspects of my job, an avid reader as well, and I love figuring out new tricks on the job.

  23. Kai says:

    @ MP (#10),
    Yes, working for free for a long time in an established industry is a good idea.
    But when you’re brand new, and you want to break into something, often, you can’t be hired without experience. Volunteering can get you some valuable background that you can work into a paid job down the line.

  24. MommaBee says:

    I’m trying to go back into my field and thought that I tried everything…Called recruiters to find me jobs, called schools for a refesher course, put ads in the newspaper and Craigslist…The recruiters told me alot of negative things- I’d need someone desperate to hire me since I haven’t worked in my field a while (due to raising a family!!), I don’t have experience in the last year so nobody will look at my resume’, etc…. I finally ventured on my own ans aed facilities if I could work for free and gain knowledge and references. I will start at a facility next week and am so happy. I do have a job that pays me, so this free work will be on my time when I’m not at my regular job. The best I can hope for is that I get a job in my field. If not, I still have my current job. But I won’t continue this free work forever. I’ll give it 3 months.

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