Business: Top Secrets to Being your Own Boss

Start Your Own business

Why not me? There is something in present in people that makes the idea of being your own boss in business a dream worth fighting for.

I work for myself. My brother does. My father did–on a much larger scale. I suspect one or two of my eight nephews and nieces will too. (This is a story for another day by the way).

It gets you out of bed in the morning. It is teeth-grinding anxiety when you take on too much work, or when there is too little of it, or when your invoices seem to have slipped into a black-hole.

And it’s tremendously hard to juggle that whole work/life balance thing when your work is your life. It’s embedded in every nook and cranny. Pushing back is hard to do. Vacation? Every day is a workday. And that’s OK. Really.

You love what you do, period. You control your own destiny, as ephemeral or illusive as that may be. It’s an inner drive that’s hard to explain if you don’t have it “engindered” in you, as Grammy would say.

For many career switchers, the entrepreneurial path is the ticket. It’s the American Dream. Just watching movie scenes from The Social Network and tracing Mark Zuckerberg’s college launch of Facebook can convince us all that it’s possible. And with years of business experience and so forth, you’re far more prepared to launch than a twenty-something.

I have interviewed hundreds of entrepreneurs and profiled some of their success stories in my book, What’s Next?, and I am always struck by their confidence, tenacity and  hope. No one questions how challenging it can be, but for most people, the reward is a payout that blows right by the financial struggles and setbacks.

It struck a chord with me. “Entrepreneurship is not simply a rational journey, Bussgang writes: “It is one that is defined by passion and personal satisfaction that transcends purely financial analysis. And, of course, there is always the hope for the big payout, no matter how long the odds.”

Here are tips to consider if you have the entrepreneurial bent:

not too late to start any business or anything

Don’t think you’re too old to start your own business. 

Bussgang tosses out some interesting studies to support this. The Kauffman Foundation reports that the median age of founders is 39 – right at the midpoint of a typical professional career – and 69% are 35 or older. Another study by Washington University professors of 86,000 science and engineering graduates showed that age was not a significant predictor of becoming an entrepreneur.

Get comfortable with salesmanship. 

How good are you at selling yourself? This is a key ingredient for those of you embarking on an entrepreneurial second act. You may have had a wonderful initial experience starting a new business or a consulting business but fail to understand that your confidence is only part of the battle; the other part is marketing yourself as you move along from those heady first few months or even years.

Brace yourself for greenhorn blues. 

It’s much tougher than you think to cope with being a beginner. It’s unnerving. You feel as though the rug has been pulled out from under you, and your base of support and confidence has slipped away. To have a second act hit, you must be sufficiently open to change in life.

welcome criticism in business and develop thick skin

Develop a thick skin. 

We all like to be treated with respect. But when you move into uncharted territory, you’re a neophyte, the proverbial new kid on the block, starting over at the bottom. This requires some psychological adjustment and fine-tuning. All of a sudden, you are making less, probably making a few mistakes. A supportive partner or best friend might be all the shoring up you need, but it is a transition phase that shouldn’t be ignored.

Make mistakes with grace. 

Easier said than done. Face it, the older you are and further along on your professional success ladder, the harder it is to accept criticism and responsibility for screwing up. Your ego just isn’t as nimble and forgiving as it once was.

When you’re in your twenties you are better equipped to handle the inevitable screw-ups and missteps, let them slide off your back with a simple shrug, and move on. Accept that trying new things means learning from your mistakes along the way. You will be in a healthier stronger place to move ahead. Doing things badly is just another step toward doing them well.

One of my favorite entrepreneurial success stories is John Sage, 50, who cofounded Seattle’s Pura Vida Coffee. After graduating from Stanford University in 1983, Sage spent a handful of years working for pharmaceutical giant McKesson, garnered a Harvard MBA in 1989, and achieved financial success as a Microsoft marketing executive. He took a turn as a vice president of a start-up high-tech company, Starwave, which was acquired in 1998 by Disney and Infoseek, leading to his “lucrative exit” as a multimillionaire, he recalls. “I was fortunate to be in high tech at the right time,” Sage says.

So he had the funds to kick-start his venture with HBS classmate, Christopher Dearnley. And the company, by all accounts, has been a winner. Like all start-ups, it has had twists and turns and challenges along the way.

When I asked John what he would have done differently, here’s what he said:

  • “I should have put a more demanding set of financial filters and more scrutiny on the basic business model. I was in a position to fund it for several years, which was great, but as an unintended consequence I didn’t really subject myself to the same rigor and discipline that I always talk about. I should have spent some more time really thinking through what it was going to take financially and operationally to scale the business.”
  • “The business required a leadership and a management team that has a different skill set than I do. I am not a good day-to-day operational penny-pinching guy. It would have been very helpful to have come to that realization much earlier. It was a combination of my optimism and, in part, arrogance—just thinking, how hard could it be? I got an MBA, right? I can do this.”

Finally: “When I sit down with wide-eyed optimistic social entrepreneurs these days, I sound like I am giving them a dose of harsh news, but it comes out of that experience.”

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