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How To Go From Employee to Entrepreneur With Confidence

 James Brey/Getty Images
James Brey/Getty Images,

by Kara Baskin

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If you’re dreaming of becoming an entrepreneur, your timing is great, just great. So says William Seagraves, who left a job in government defense to become a tech consultant and launched Catch Fire Funding, where he counsels midlife corporate workers on how to start and fund businesses. In an era he says is ripe for a second act,going freelance or starting a company, he shares his secrets in a new book, Be Your Best Boss: Reinvent Yourself From Employee to Entrepreneur. He talked to Life Reimagined about how to make the leap.

When do you know you’re ready to take that step from employee to self-employed? 

Many people are blindly progressing in their careers but have an uneasy feeling about their current life and career paths. They believe they could absolutely be happy and successful as entrepreneurs. But the misconceptions about business ownership and the constant negative response from peers, friends and family hold them back from making the leap. Only when someone can rise above the negative chatter, ask themselves the critical questions, and overcome their self-doubts are they ready to be an entrepreneur.

One of my favorite questions to ask a new client is: When was the moment you absolutely knew you wanted—needed—to be an entrepreneur? Everyone’s answer is different, but they all can recall the exact moment and situation. A drive in the car by themselves, a day on a beach, at a music event or concert, after a fight with a coworker or their boss, during a conversation with a spouse or life partner, while talking to a trusted advisor or mentor. The best way to describe it is like a mental switch is flipped and they’re ready to move forward.

Only when someone can rise above the negative chatter, ask themselves the critical questions, and overcome their self-doubts are they ready to be an entrepreneur.

How can someone who's had a lifetime of bosses learn to live without one?

Surround yourself with talented and well-meaning peers, advisors, mentors and employees. Join community and business groups so that you’re not running your business in isolation. I have learned a vast amount about successful business management by participating in business peer groups and listening to what challenges other businesses face and watching how the owners reacted and seeing what those results were. I find it is much easier to learn from other’s mistakes.

Why is the current economic climate ripe for a second act?

There are some long-term considerations and some more immediate ones. Most people over the last eight years or so, if they were lucky enough to maintain their jobs through the recession, were doing so in a position of fear. People weren’t if sure they would have a job next week or next year. We’ve had a recovering economy in the past two years, but the market became more volatile back in August. My number of inquiries jumped. People are afraid of going back toward that. We’re in a new phase of uncertainty. This isn’t our parents’ era of staying in the same job for years.

Isn’t working for yourself uncertain, too?

One of my local clients, Danny, was in commercial construction. He decided to open a liquor store. Well, what do construction and liquor stores have in common, you might wonder? He found a bare-shell space, perfectly located, and he leveraged his skills of designing, imagining, lining people up and overseeing the build-out of his liquor store. He was able to open it at a discount. It’s less risky to use the skills you already have to segue into something new.

I want people to know that they're better prepared than they might think they are. People come to me and say, “I’m not a business expert.” But, unless you’re working for the government you’ve worked for someone else’s business for years, right? Take all of the assets you've learned on somebody else's dime and put it to work for you. Parts of operating a business can be broken down into things you do now, every day, whether it’s managing budgets or marketing or managing a team.

How can people determine the right business fit before getting in too deep? 

Use a diversified discovery process. I coach people to have an effective process to consider different businesses, at least at first. What is the day in the life of a business owner in that field? Do they come in at 8? Leave at 5? I have quite a few successful clients who are in the window cleaning or house-painting or other non-sexy businesses. They find it suitable to them. It’s more about lifestyle. Enjoying the lifestyle, not always what you sell or represent, is what drives the highest contributor to the probability for success and fit.

What are some common pitfalls or mistakes that entrepreneurs face?

Don't sit in your store and hope people walk in the door. Don’t work in a vacuum.

You need a team of support and professionals, from accountants to attorneys. Meet people, network, join national peer groups, find a mentor you know and trust to give you honest, unbiased advice. It’s your business, but don’t go it alone.