If you’ve read Tim Ferriss’s popular book The Four-Hour Workweek, you’re familiar with the concept of seeking independence in your work, being in control of your time, working remotely, and then using your free time to indulge in things you love.
Independent, footloose and fancy-free, risktaking. That may be the popular profile of a self-made entrepreneur, but it’s not the only one. In 2012, the word “entrepreneur” almost seems old school. A buzz word that we’ve thrown around since the early dotcom days (if not even earlier), it’s easy to overlook just how challenging and multi-faceted the self-reliant career path can be. It’s not JUST about self-reliance. After all, you can use the general principles of entrepreneurship to forge ahead in corporate careers too, but the buckle-down, work-hard, risk-often approach does not an entrepreneur, in its purest sense, make. Being passionate and working hard isn’t enough. Results COUNT.
I got to thinking about this when I read Lara Galinsky’s recent post in the Harvard Business Review about why not everyone interested in good-for-society causes should be a social entrepreneur. Her discussion is focused on a certain sub-set of businesses, but just the title of her article alone made me wonder if I’m cut out to be an entrepreneur. And I decided: no. Not right now, anyway.
I’ve been freelance writing for several years now, but I have never made the decision to pursue it full-time. It’s not because I’m in debt, which, as Suzanne pointed out in her post yesterday, can derail us from pursuing dream careers. Rather, there are several specific things that an entrepreneur-in-the-making should cultivate before making that leap:
Be financially ready. Unless you’ve sat down and recalculated your budget without the consistency of biweekly income, you’re definitely not ready to make a go. Take your regular income completely out of the equation and tabulate ALL expenses, such as utilities, rent, gym memberships, health insurance (now that you’re the one footing the bill), etc. It’s one thing to put aside six months’ worth of living expenses, as financial experts tout as the ideal number. Re-budgeting, even from a purely hypothetical standpoint, is a rude awakening that will put your new lifestyle into real focus.
Have a stream of income in your new field. Do you know there are people who completely quit their full-time careers to pursue their “dream” and also, by the way, aren’t yet earning a penny in that second field? It’s O.K. to rely on a partner’s income or a trust fund until you earn your first paycheck in your new business. For those who are single or without a nest egg, it’s really not enough to rely on savings.
It’s not just financial, it’s psychological: your first small gig will boost your morale and tell you hey, this IS possible and also help you build momentum. If you can’t land something small, how plausible is a full-fledged business?
Be good at forging and strengthening new connections. Too many times, I’ve heard well-intentioned but generic advice when it comes to making connections. Go to events! Bring business cards! Network! (Cringe.) It wasn’t until I moved to New York City and was forced to start my entire social network from scratch that I realized networking might take some practice for me. For one, I’m a bit of an introvert. Two, it’s one thing to make new contacts; it’s an entirely different social skill to cultivate ongoing friendships and business connections with people you don’t see every day.
If you make the decision to go the entrepreneurial route, you will need to be comfortable building relationships from the get-go, and giving time to let those relationships grow. If you’re like me and the whole idea of “networking” makes you break out in a sweat, start small and pressure-free by joining a book club or a group volunteer activity. Get GOOD at it.
Building up skills and smarts before making the switch to a entrepreneurial lifestyle might seem counterintuitive. Just forget the notion that all entrepreneurs are pure risk takers who are born and not made.

Excellent advice Pam! I’m working full-time while building a health coaching practice on the side and cannot financially walk away from my job income. I spend about 10 hours+ a week on marketing efforts for my health coaching practice. Thanks for sharing.