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This Year, Take Some Risks

Most of us don’t like risk.

We buy insurance. We work for a paycheck. We put our money in an FDIC-insured savings account even though it pays less than 1.0% interest.

These things aren’t necessarily bad; a little bit of caution is a good thing.

But when you become conditioned to reject nearly any risk in your life, think of how this influences your behaviors and, more critically, how it impacts your life.

  • you don’t talk to that beautiful guy/girl at a party because you’re afraid of rejection; you stay single
  • you don’t take credit for an outstanding job at work because you’re afraid others will think you’re bragging; somebody else gets promoted
  • you don’t follow your passion because you’re afraid others will call you crazy; you have major regrets in 30-40 years

Risk is good.

Risk creates progress.

(In this video, Peter Diamandis explains why he’s comfortable asking people to risk their lives in pursuit of the X PRIZE, which he created.)

But you don’t have to risk your life to rocket into space. You don’t have to quit your job to become an entrepreneur (unless you want to, in which case, you probably should). But this year, after your resolutions to hit the gym and stop buying lattes have failed (and most of them will), resolve to take a risk or two.

Talk to a pretty stranger. Go skydiving. Start freelancing. Leave a job.

There is a line, of course. I’m not telling you to stake your life’s savings on red at the roulette wheel. There are big risks and small risks. Some risks have positive expectations, like the strong likelihood a boss will grant a hardworking employee’s request for a modest raise. Some risks have negative expectations—roulette, for instance.

Of course, not all risks will pay off.

But success is earned on the back of many such small risks, and the obdurate takers will be rewarded with far more than the costs of their failures.

I know this isn’t specific financial advice you might be expecting, but it is—most importantly—actionable. You can resolve to take risks this year. And you can start today.


I’m taking risks all the time. And recently, I took a big one:

Last month, I left my day job to work full-time on Money Under 30.

Now, if you’ve been around awhile, you’ll know that for a few months in 2009, Money Under 30 was my primary focus while I juggled some other part-time projects after moving from Boston to Portland, Maine to be with my wife. I then began work as a marketing manager for a software company until I left that job last month.

What changed?

In 2009, Money Under 30 was ready to be worked on full-time, only I wasn’t ready to do it.

I had just moved to a new city. I was getting married. I had repaid most of my debt, but I needed to save a lot more before feeling comfortable being self-employed. And I’d soon be a dad.

I know that some people would’ve made the leap sooner. But, then again, some people wouldn’t make the leap at all.

I admit, I hesitated.

I liked having two incomes. (Indeed, I still believe in diversification, and will be consulting with my old employer and some other contacts to ensure my livelihood isn’t 100% dependent on this blog).

Ultimately, however, I’ve always known that I wouldn’t be truly happy unless I were working for myself. It’s a personality thing. Some people work well—or at least tolerate—working under supervision. I can’t. It makes me resentful, even angry. I would get the worst cases of road rage because of how much I dreaded marching into work for 8:00 on somebody else’s schedule. And I’ve had GREAT bosses. I’ve gotten along with all of them. They’ve been nice people and competent managers. But that doesn’t matter. I just need set my own hours, and most importantly, go at my own creative pace. If I want to be working on A but you tell me to do B, I can’t do it. I simply can’t. If I try to focus on B, I’m too busy thinking about A and won’t get anything done. Despite all this, I waited to take this risk because of the same reason people don’t ask strangers out, ask their boss for a raise, or make any big change in life…


Not fear that that I wouldn’t succeed on my own. Of that, I’m quite confident. But the fear of what other people think. The fear that my parents would think I’m throwing away a “real career”. The fear that my friends would think, as a blogger, I must just be sitting on my ass eating bonbons all day.

This is the worst kind of fear, of course, because it’s totally irrelevant. If you’re skydiving and afraid your chute might not open, at least that fear serves a purpose; it might remind you to inspect the parachute.

The fears that prevents us from taking little risks in our daily lives, however, are mostly unnecessary. Unfortunately, that doesn’t make them any less paralyzing, and you need to overcome them.

Ultimately, in order to take the risk I needed to take, I had to face my fears. My friends and loved ones can think what they want. I don’t care. I’m doing what I love, and I’m far happier because when I get up every day, I get to work on creating my own material that will help you. And that’s awesome.


That’s my story, but I want to know: What risk(s) will you take this year? How do you expect it to change your life? Share with us in a comment. (And when you follow through, don’t forget to circle back and let me know how it worked out.)


Published or updated on January 3, 2012

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


We invite readers to respond with questions or comments. Comments may be held for moderation and will be published according to our comment policy. Comments are the opinions of their authors; they do not represent the views or opinions of Money Under 30.

  1. Tracy says:

    Great post! I’m taking a big risk this year, too – buying my first house! Just starting with mortgage pre-approval and Realtor-shopping, but hoping to sign on the dotted line by summer!

  2. Mike says:

    Thoughtful article; enjoyed it.

  3. Pam says:

    That’s so cool that you are taking risks this year and that you want to help others! I admire your courage.

  4. David,

    I am really happy to hear you have decided to take the leap. I am looking forward to watching you take the business to the next level.

    You won’t ever have to look back on your life and wonder what could have been. You are an inspiration to us all!



  5. Peggy S says:

    Good to see, that I’m not the only one not beeing overly cautious. Taking risks sometimes definitley can benefit you, even if you don’t see the result right then. It might seem wierd in the beginning but you’ll learn (nearly) always from mistakes, so even, if it didn’t work out how you wanted it to, you will know for the next time.

  6. Great job on taking the plunge! I am sure it will be successful! I certainly understand your tendency to diversify though.

  7. No One Special says:

    OK, just negotiated a 40% pay cut to work part time and support to start my own business! Going to be an interesting 2012….

  8. Gary Morgan says:

    Great article and confidence booster. If we are reading David’s blog, it’s because many of us are in the beginning steps of taking our 1st big risk (as I am) or because we want to make a change which can be a risk in itself. I personally have a 2YP (2yr Plan) to be self-employed and able to leave my current full-time job & in the meantime set out smaller goals leading up to that mark. (6mo to figure out a product to sell, weekly meetings to keep it fresh etc) As David points out in his ‘Richer by the Week’ workbook, our longterm goals are often too big for our mind to comprehend when we are struggling to make ends meat, so I’ve ‘chunked’ it down to a shorter, more attainable piece by piece which will ultimately complete my life goal puzzle! We all deserve to reach our dreams, some of us may start later or take longer, but the thing that matters is that we are in fact dreaming and taking action. Afterall, it would be Un-American not to; Right?! Good Luck everyone!

  9. Ashley Webb says:

    I am reading this post while commuting home from a job that a don’t love because I have been afraid to follow my dream and I think this is just the push I needed to stop worrying and go for it. I love your blog, good luck and thank you for inspiring the rest of us to follow our dreams! :-)

  10. Kimberly Stromgren says:

    I am saving this post of yours because I NEED to come back to it. I need to admit to myself what it is I really want to do with my life and have the courage to go for it no matter what people think.

    I’m not ready to tell you what that is yet…all I know is that it involves making money. Because I’m tired of being supported by my husband. Tired of never going on vacation because he doesn’t want to go. So many things.

    It’s time for me to live.

  11. Congrats! I am also starting 2012 as a self-employed freelancer/writer. Honestly, I wasn’t quite ready to leap yet, but some extenuating circumstances with my employer pushed me to go ahead. It’s amazing how confident I am that I can make this work; I know there’s a chance I’ll have to look for a job, but I believe I can succeed beyond my wildest dreams.

    I’ve done a lot of searching about personalities that just aren’t well-suited to working for other people and there isn’t much out there. But I know I’m one of those people, and working for myself has been wonderful so far!

    Best of luck – I hope you’ll keep us updated!

  12. Brian says:

    Great post! I am naturally risk-averse but I try to be proactive about taking “smart” risks. When I do take risks and they pan out (or even if they don’t), I feel so much better about myself afterwards for being true to myself and going after what I want.

    In 2012, the big risk I will take is to quit my job and change careers only a couple years after graduating from college. After graduating with a business degree and working in software sales for a year or so, I will be doing a “180” and going into a healthcare profession such as MD, PA, or Nursing.

    I actually did the first step in late 2011: I quit my software sales job in December, after completing my undergraduate business degree only 17 months prior in May 2010. I didn’t quit because I wasn’t cutting it in sales; in fact, I was doing pretty well at sales and had recently been promoted. I wasn’t a superstar or anything but could certainly get by. With all the bad news about the economy these days, many of my friends and family thought I was lucky to have a decent job at age 23.

    The only problem with all of this is that I no longer felt fulfilled by what I was doing. I was never excited to go into work in the morning, and I felt that my personality and values weren’t the best fit for a sales job. I am now eagerly looking forward to my “post-bacc” science classes which will begin one week from today. I will also start a part-time job soon waiting tables to pay for my classes and living expenses. I have some savings and will work part-time, and my main financial goal right now is to avoid taking on debt until I complete my pre-requisite classes for graduate school. For graduate school (Med School, PA School, or Nursing School) I will definitely need to take out some loans.


  13. Congratulations! I became a self-employed entrepreneur at age 27, and I love it. There’s so much more upside potential, in my humble opinion, when you work for yourself. The risk is higher, sure. But so is the potential reward.

  14. Adam says:

    Congratulations David!

    That reminds me of ‘The Flinch’ by Julien Smith. If you check out Amazon, the kindle version is free. I just started reading it the other day, and he equates this ‘fear of risk’ with ‘the flinch’ (as in, flinching to avoid a punch)….keeping us safe in the status quo, etc.

    Good parallels, here and there.

    As for me, I had started my own stock website a few years ago, but lost interest. It turns out I was much more interested in trading stocks, than teaching about trading stocks. I hope to fire up a new, more personally inspiring website soon. With any luck, it’ll hold my interest more AND become another source of income for me…perhaps enough for me to leave my job, too.

    Also, I’m 11 monthly payments away from paying off the house (the car was paid off last month). I’m paying double per month, so it’s a bit of a risk to have that money unavailable each month for unexpected expenses, but I think it’ll be worth it. Debt free by 31…exciting stuff!

    Best of luck!

    • David Weliver says:

      Thanks much, Adam. I’ll have to check out “The Flinch”. Congrats on being so close to your own goals this year. Debt free–mortgage included—by 31 is quite the accomplishment!

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