Updated on 12.19.08

New Year’s Resolution Workshop #5: Launch My Dream Career

Trent Hamm

new year's resolution workshopBetween Christmas and New Year’s, we’re taking a look at five common New Year’s resolutions that people often adopt for their finances, evaluate some of the traps that people fall into with regards to that resolution, and come up with some real actions that can turn a challenging New Year’s resolution into a success.

I can’t even tell you how many times I offered up some variation of this resolution at the turning of the year. So many times, I pledged to give an intense effort toward launching my writing career, and so many times, I’d start off on the right foot, writing with a vengeance.

And yet, for so many years, I didn’t find any success at all. I’d mail things out and see rejection letters. I’d write and write and write and yet I would find fatal flaws in all of the results. And eventually, I’d tell myself that it was a nice dream and file it away somewhere.

Eventually, I realized I needed to try something new, so I started sharing my writing online here and there. I’d contribute to forums and a wide variety of general interest sites. I started a blog or two that didn’t really go anywhere. And I kept feeling little stings of failure.

Yet, through all of it, I kept going. I didn’t give up. I worked hard at my “real” job, but in the evenings, I kept up with the writing. Eventually, I started writing about personal finance on The Simple Dollar and, for some reason, it clicked like nothing else has clicked before. And now, because of the site’s success and other positive events, I’m able to write full time – and I even allow some of that time for me to chase my fiction writing dreams.

What did I learn from all this? How exactly can a person transform a resolution to chase after their dream career into actual success in following that path? Here are five key lessons I learned that can be applied to any career resolution.

Practice. Every career requires proficiency at some specific skill or set of skills. Perhaps your career requires mastery of a musical instrument. Perhaps it requires successful composition of written words. Maybe you need to be a skilled computer programmer, or effective at speaking in public.

Whatever those key skills are, identify them and practice them daily. If you want to be a writer, write every day. If you want to be a musician, practice your instrument every day. If you want to be a politician, find every opportunity you can to speak in public.

Such practice should fill a significant part of your spare time. If not, you’re not truly working to make that dream career happen.

Learn what the career actually entails from practitioners. Many people who dream of a particular career have a romanticized version of what the actual day-to-day work in the career is like. Instead of picturing the reality of the situation, they envision the things they would most enjoy doing. For example, when I dreamed of being a writer, I didn’t particularly think too much about negotiating with publishers, doing media appearances, or planning ahead for my writing. I just thought about the joy that I got out of writing.

Why is this important? Quite often, success in a career requires adopting some unexpected skills. I would have never believed, for example, that networking skills or public speaking skills or time management skills or accounting skills could be useful in a writing career, but they’ve all come in handy for me over the past year or so.

Spend some time talking to a practitioner of the career that intrigues you and find out what exactly the work is like and what skills will have to be brought to bear in order to be successful. Through this, you might also find some extremely useful tips that can provide insight as to how to find success.

Try new approaches. For years as a writer, I believed that the value in writing was in maintaining your copyright as a gold standard. I resisted any situation where my writing might be easily shared with others and I kept most of my work to myself.

Eventually, though, I built up the courage to start sharing my writing online. At first, I convinced myself that I was just writing to receive feedback from readers, but over time, I began to realize that I was quite happy simply to have readers. Now, the vast majority of my writing is published online for free – instead of charging for the writing itself (as would occur in most copyrighted situations), I give away the writing and put up ads to support the costs of doing so.

It was a new approach for me, far different than what I was used to. It took a lot of courage for me to move in that direction, but when I did, it opened a lot of doors.

If you’re not finding success with your current tactics, try dropping them and trying something entirely new. Look for new angles, and see what others are doing that is bringing them success. You may find the success you’re seeking just by trying a new angle – or combining some ideas that you previously hadn’t combined before.

Expect some failure. I know that when I first started trying to chase a writing career, I firmly believed that I was going to be successful quickly. I had passion. I believed I had noteworthy talent. And I also thought I had a very valid gameplan.

It turns out all I really had was passion, and even that didn’t extend as far as I thought it would.

Any time you try something big, new, and audacious, you’re going to fail along the way. In fact, you’ll probably grow weary of hearing the word “no” over and over again.

The best way to prepare for this is to expect that it will happen and, more importantly, don’t put all your eggs in one basket. Don’t quit your current job to chase the big dream. Instead, hold onto that day job as a steady source of income until you start finding success – or at least find a workable, realistic plan that will guide you there.

Look for any and all freelancing opportunities. Since you’ll likely be taking the first big steps in your new career in your spare time, one great way to get your feet wet is to look for any and all freelancing opportunities that relate strongly to your career of interest.

For example, if you’re thinking of starting a catering business, start slow and look for small jobs that you can handle in your spare time. If you’re dreaming of writing, try selling shorter articles that you can easily write instead of huge, complex pieces – or take up blogging. If you’re a musician, look for local parties that you can play at for a few dollars instead of trying to get big gigs all the time.

The key is to get work and get yourself out there to be noticed by others. You’ll build up your resume along the way and likely meet a lot of people who will associate you positively with your endeavor. These connections will very slowly begin to open more doors for you.

Good luck!

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  1. Johanna says:

    A good list. It seems to be mostly applicable, though, to those whose “dream career” involves self employment in some form. When I made the transition to my present career, I didn’t do any of those things – except for expecting some failure. :)

    If you think your dream could be satisfied by a salaried position with an employer, and you see an ad for such a position, go ahead and apply for it. Even if you’re still in the early stages of networking, even if you don’t have a lengthy resume to show them, even if you’re not 100% sure you’re what they’re looking for. You might be pleasantly surprised. I was.

  2. Mike McMahon says:

    In my tenth year of working for a large company, I attended a Tony Robbins seminar. The year was 1989. I created my dsecription of my dream job along numerous other things. Fast forward to today, and I still working the same large company. Fortunately for me, the company has gone out of business and now I am about to embark on a new voyage in pursuit of my dream job. Despite the significant delay in pursuing my dream job, I can truly tell each of you, the mere exercise of having done that ezxercise 20+ years ago has positioned me to have a great chance in succeeding.

  3. CPA Kevin says:

    The idea about talking to a practitioner in the field already is a great one. Like you, there are several skills I never realized I would need until I actually became an accountant.

  4. I really liked this post. I’ve decided in the new year that I want to make a change from my current job- either by pursuing a promotion; or if I don’t get it by my third year anniversary with the company; to go out and find another job. In the meantime, I’m working on what I really want to do- write about travel. If I go down the job-hunting route I want to find a job that supports my travel writing dreams- either by sending me places or have me writing on a regular basis.

  5. Anne KD says:

    A little over two years ago I started my own business, which went through a long slow lingering death last summer. I’m probably going to start it up again with some changes. I’m also trying a couple other things as sidelines. Your article comes at a good time and I’m feeling more motivated to learn more and work more at what I like doing plus the little things I’m not good at yet.

  6. Studenomics says:

    One thing that I will state about my dream job is that as much as I am looking forward to it I know that I have a long way to go. I am really realistic with myself and I understand that it will be a few more years of education and practical experience before I can move into a dream career.

    I find that all my friends always talk about the dream job, but really if you haven’t put in the effort, who do you deserve it?

  7. Modern Gal says:

    Consider the non-profit sector. Find a cause that you are passionate about, this might range from working with children, helping the elderly, or environmental conservation. The sector is in need of a ton of skilled writers, computer programmers, business planners, etc…

  8. JE Gonzalez says:

    Amen to that Studenomics,but as long as you know exactly what you want, it will come to you. My dream job is working at Pixar Animation, and it will be a long journey. Likewise, I realised this year that making money through leverage is the best thing I have learned.

  9. Ken says:

    I just began blogging this past week for the first time. I enjoy the topic of personal finance and am going to see where this goes. I enjoy your blog and am open to suggestions on developing a strong blog. Have a great new year

  10. Your Friendly Neighborhood Computer Guy says:

    Great list. This is going to be my resolution for a few years, as it’s going to take me that long to save up enough from freelancing as a computer consultant to have the cushion to go full-time with it. But each year I take another step toward that dream.

    That could be another point to add to your list…”Take things slowly, step-by-step”. It’s not gonna happen overnight, and don’t expect it to. But do something small everyday that will move you toward that goal.

  11. Babie T Nice says:

    I have to say Trent, that you write exceptionally well and your years of practice and hard work have paid off. Good for you! You followed your passion and not you’ve made it.

  12. Gillian says:

    Thanks so much for covering this topic. These are important reminders, especially for anyone who is just starting out in the world of jobs and careers. This will definitely serve me well as I try to stick to my 2009 resolution to keep up with my writing!

  13. I went freelance six months ago and haven’t looked back. Thanks for a great post that I will refer to throughout 2009!

  14. I think you’re spot on about practice. I think if that one aspect is in place, everything else can come out of it. But if practice isn’t there, none of the other stuff matters.

  15. Sorry if I missed this somewhere else, but are you planning on reporting your earnings on your blog for 2008?

    Some people expose the numbers…I understand if you don’t want to. As you probably know though, it creates a system of accountability to both you and your readers if you choose to.

  16. Stef says:

    Let me express a pessimistic thought about “expecting *some* failure”.
    how much failure is reasonable to bear?
    I mean, when becomes just decent saying: ok i give up?
    i know this answer is also very depending of the single situation, but self-help manuals flood us with positive thinking thoughts and never give us the tools to stop when it does not work.

  17. Savvy Frugality says:

    I am fortunate that I have already worked in my dream job and spent more than 20 years doing so. When my “dream job” was no longer profitable, I started looking for other things to do and found another career that was related, but paid much more. I also do a lot of freelancing which allows me to pursue outside interests as well. Maybe one day I’ll follow the “Kramer Lifestyle” (yes, the Seinfeld character) and not really have a career but just things I do for money that I consider fun.

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