Wednesday, August 24, 2011

Smart risks and looking before you jump

I've had a lot of time to think lately, and a topic that comes across my mind is, "How did I get here?" Simple answer: by car (yes, my humor is that lame). I'm about to turn 28, living in Florida, and trying to make a living as a freelancer. Aside from getting a year older, never in a million years would I have imagined myself in the other two situations. Freelancing has always been an intriguing option, but realistically I imagined myself getting old in a secure office job. A recent article in the New York Times on those that have quit relatively secure careers to follow their dreams, only to be met by unexpected difficulty, also caught my eye and had me questioning, "Did I make a bad decision?"

In general, I am not a risktaker. I've never been sky-diving, cliff-jumping, or tried an extreme sport. My belly flops just thinking about the high diving board at the pool growing up. I'm not scared of heights, but something about jumping into the unknown makes me a little queasy. But there are some things I think are worth it—putting myself out there on a blog, for example, or moving across the country alone for graduate school.

Not all risks are created equal, however. Some questions to keep in mind when you're making a risky move (geared toward career, but can be applied to other things as well):
  1. Am I qualified? This could be an educational credential or just years of experience with a trade or hobby. If you can, try to get some experience under you belt before you branch out full time.
  2. What actions can I take to make this work? Success isn't all that hard to figure takes work, work, work, work, work, work, and a smidge of luck.
  3. How long will it take? Be realistic. For example, if you're opening a restaurant, don't expect a profit in your first year. This will also help you know when to cry uncle.
  4. What is the interim plan? Do you have a second income in your household that is enough to live on, will you be living off savings, or are you looking for a part-time job to meet your basic needs?
  5. What is the worst case scenario? Think about what you could lose if your plan doesn't pan out. Upfront costs, missed payments and risk of default or foreclosure, strained friendships or business partnerships.
  6. How would I recover from said scenario? If you had a career before you took the risky move, would you be okay going back to that career?
Even after taking all these questions into consideration, I still find myself scrambling for words when people ask, "So that's a career?" or "How do you find work doing that?" I'm only one week in and short on answers, but ask me again in a year.

Have you ever taken a risky move that others questioned? How did you plan ahead, and how did it work out for you?


  1. I didn't plan ahead, which is utterly dumb. I quit my very secure teaching job and decided I would figure it out. People were concerned, but for some reason I was not, probably because I am married and my husband (luckily!) has a job that can more than take care of us. I think that is probably why I quit without a plan. Not a smart idea!

    I took the summer off to play and decide what I was going to do. Then, I opened my wardrobe consulting business. I also picked up a few tutoring clients to supplement my income. Two years later my business is is closer to where I want it to be, but not quite a full-time job yet. It was the best decision I ever made, but I must admit if I were not married with extra income coming in, I don't know if I would have been brave enough to quit my teaching job.

    I am excited for you and to hear all about your new career!

  2. Don't get too scared, Angeline, you're going to be great! You've got the experience, and you've already got some connections for projects, so it's all going to work out :) I came across this great blog recently, (this link goes directly to her freelance-related posts), and she talks a lot about freelancing. She's about a year in, and she's been documenting the transition (among other things) on her blog. I highly recommend taking a look for some support, practical advice, and inspiration!

  3. I have to forward this to my husband because he is the big risk taker between the two of us. He is the one with all of the great business ideas and financial know-how. I am the saver so I am always staying well within the box.

  4. Ha ha, ok, that article is not exactly positive inspiration huh?!

    But a lot of freelancers do great! Of course quitting a 450$ an hour job is not the most reasonable thing to do, especially is your are no charging the right fees for your new work and all...

    But I think these are extreme situations too! I have to say as a new freelancer I can get a little frustrated over money sometimes (or lack thereof) but there is so much more to life really.

    And the thing is: no situation is irreversible! If you don't like freelancing, maybe you'll get a regular job. Or maybe life will send you an opportunity. We tend to worry too much!

    Go Angeline go!!

    Virginie ♥

  5. @ basiccravings - I hear ya! I am the same way. If my husband wasn't pulling in what we both made put together back in CA, I'd be back in an office, no question. But since we're both used to living off of one full-time + one part-time income, our ability to afford basic necessities (and still squirrel away some money) won't be affected at all. Congrats on making it work! I have to be honest...I'm in a bit of the beginning lull right now, too...I just need to clear my head a little mentally to get into the game, I guess. Good to hear I'm not the only one!

    @ ashley - oo thanks for the link! There are so many great blogs out there I love hearing about new ones. I think I'm still in the transition stage, but I already have some projects coming in to keep me busy, which is good.

    @ Virginie's Cinema - Seriously, right? At least all but one of the folks in the article said they would have made the decision if they had to choose again. I agree--nothing is irreversible! A former freelancer friend recommended that I give myself a minimum amount of time, though, since success isn't automatic. So I'm giving myself a year to see how it goes. At the end of the year I'll reassess and consider going back into the office.


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