Lessons from a Recovering Doormat

I have a terrific guest blogger today—Laura Vanderkam, a New York-based writer and author of Grindhopping: Build a Rewarding Career without Paying Your Dues (McGraw-Hill, 2007) Grindhopping details alternatives routes if you don’t want to stay in a job you don’t like, that doesn’t pay well and keeps you working too many hours. Whether it’s freelancing, starting your own biz, consulting, etc., the book details how to blaze a trail to achieving a way to earn a living that you find rewarding and that adds to, not depletes your happiness.

I’ve written about earning a living doing what you love in previous posts. Often the hardest part is figuring out what to do. Deciding What Do You Really Want? begins your path. Then you must begin the process of Finding Your Passions. Can You Really Live By the Grace of Passion? YES you CAN! There are enough successful Grindhoppers who prove it’s possible. Laura interviewed some of them.

Grindhopping gives you many details and examples of how to do that. Reading about how other folks chose to take their destiny into their own hands can give you many tips for your own path, and motivate you at the same time! Laura’s post below discusses how to get up the courage to take a big risk, based on a chapter of Grindhopping. That’s often what most of us need to get going—the fuel to light your fire to go for career happiness. If you have the ability, the ideas, the DESIRE to choose your income path, etc., ask yourself:

What’s the Worst that Can Happen? No, Really, the Worst!
by Laura Vanderkam

About two years ago, I interviewed a rather precocious young entrepreneur named Mena Trott. Not yet 30 at the time, she and her husband Ben had been getting a lot of attention for their blogging software company, Six Apart. They already employed well over 100 people, and Mena had been named one of PC Magazine’s 2004 People of the Year.

But, Mena informed me, things had not always been easy for the Trotts. She and her high-school-sweetheart-turned-husband went to work for a dot-com during the Silicon Valley boom. Then they got laid off. During their protracted period of unemployment, Mena started keeping an online diary about her life that she shared with friends. She wasn’t particularly happy with the available web-logging software, so she and Ben developed better tools for themselves and their friends to use. They didn’t plan to start a company, but if people liked the software, well, the Trott Rent Fund would take donations.

They launched Movable Type version 1.0 on October 8, 2001. That was not a particularly auspicious time for Internet businesses. But a reasonable number of people downloaded the software. They got a lot of positive feedback, and the donations coming in actually did pay their rent. Since the couple had some savings, they continued to work on their product.

But that summer, they had to make a choice. Ben was offered a “good” stable job. You know, the kind with a career track, benefits, etc. Should they go with the easy way and take the steady paychecks? Or should they stick with the 70-hour, underpaid weeks?

In the end, they decided to commit themselves to Six Apart. That turned out to be a wise choice. As blogging took off, so did their software. An investor actually dragged them to Japan to tell them why they needed funding. Headcount began to rise. Millions of people now share their wit and wisdom online with Six Apart’s tools.

But none of that was clear when Ben decided to turn down his job offer. I asked Mena how she and her husband had been able to take that risk. What was their philosophy? “It’s important not to be fearful of things,” she told me. “It’s easy enough to recover from minor mistakes that you don’t have to be paralyzed into not doing anything.” Along the way, she also started making a calculation: What’s the worst that could happen? “If this company failed tomorrow – God forbid – I’d still feel like I’ve learned so much that I couldn’t have learned otherwise,” she said.

After interviewing approximately 100 young entrepreneurs for my recent book, Grindhopping: Build a Rewarding Career without Paying Your Dues, I realized that Mena isn’t the only successful young person who’s adopted this philosophy. Most of my “Grindhoppers” had recalculated their approach to risk. When faced with a big choice, they asked themselves five questions:

• What is the worst that can happen if I don’t take this risk?
• What is the worst that can happen if I do?
• Is the worst that can happen if I stretch myself really all that bad?
• What is the upside of taking this risk?
• What can I do to hedge against the downsides?

The order of these questions is important. Most of us ask the second one first. When we’re considering a big risk, we think of all the horrible things that can happen. If we quit our mediocre jobs, we’ll soon be broke and living on the street. If we audition for a community play, we’ll be laughed off the stage. If we bicycle through Europe alone, we’ll get lost, get robbed, and probably get horrible food poisoning to boot. Humans are risk averse; it’s natural that we’d worry about these things.

But the problem is that we underestimate the pitfalls of not taking the risk we’re considering. Sure, if you quit that job you don’t like, you might wind up broke. But if you stay for years in a job that doesn’t make you happy, you’ll grind down a little of your soul every day. You might never have the life you want. And that is a big risk, too.

Indeed, it might be a bigger risk than the actual change you’re considering. I finally came around to that third question – is the worst that can happen if I stretch myself really all that bad? – when I faced a big choice a few years ago. I’d always wanted to be a writer livi
ng in New York City, so when I found myself, at age 23, with no job, I realized I could give it a shot. I didn’t have a lot of money. New York is very expensive. My mind wandered, naturally, to the second question. I had images of myself squeegee cleaning windshields of my college classmates who’d made “smarter choices”, like going into finance.

But then I forced myself to ask the third question. Did I really think I’d be stuck squeegee-ing windshields for spare change? Even as a kid I’d always figured out ways to earn money when I needed too. I could make my rent babysitting, slinging lattes at Starbucks, or writing press releases at a travel marketing firm. I actually did the latter part-time for three months until I got a book contract and didn’t need the safety net (see question five – if you’re bicycling through Europe alone, for heaven’s sake, take a map and stash some extra cash in your sock!). The worst that could actually happen, I decided, is that I’d eventually be older, have missed out on a few years of the savings I might have accrued while working a corporate job, and I’d be jaded about the writer-in-New-York thing. But at least I would have tried it. I forced myself to look rock bottom in the face, and decided it wasn’t that bad.

And maybe, just maybe, I wouldn’t have to experience rock bottom first hand. The nature of risk is that big risks can bring big rewards – something we often forget when we’re weighing big choices. Yes, the worst could happen. Mena and Ben could have watched their company fail after another year. But the best can happen, too. I stepped off the train at Penn Station on September 2, 2002, and within a few months, realized I’d made the smartest decision of my life. In my first full year of freelance writing, I doubled what I’d made in my previous “real” job. Because I was living in Manhattan, I got to do such only-in-New-York things like sing in Carnegie Hall with one of my choirs. I even met my husband in a bar in Greenwich Village. None of that would have happened if I’d let the squeegee image dictate my decision.

So now when I’m faced with big choices, I try to remember what Mena Trott and other entrepreneurs like her have realized. You don’t have to be a gambler to take a big risk. You just have to realize that not taking a risk is a decision too—a decision with its own downsides. Viewed that way, there really is no reason to be fearful of things.

Check out Grindhopping by Laura Vanderkam if you’re looking to change your work life!!

If you enjoyed my post, please leave a comment and/or click on the bookmark and write a short review at some of the sites, especially Stumbleupon and Digg. Thanks!

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