Outside the Box: Are you switching careers? Keep this in mind when you get discouraged

In her book, she writes about her own journey to becoming an entrepreneur. “I just didn’t know where to start. I had plenty of skills: I’d been a reporter and a political campaign operative; I could write and speak well…but the rest of entrepreneurship was a black box. So I decided to learn.”

Read: 3 questions to answer before you make a career change

For a full year, she committed to studying while still working a full-time job as an executive director of a bicycling advocacy nonprofit. On Saturdays, she took courses at the local adult education center on topics like writing a business plan, designing better PowerPoint slides, and basic bookkeeping. She became a regular at her local library, checking out business bestsellers from Michael Gerber’s “The E- Myth,” Keith Ferrazzi’s “Never Eat Alone” to Jim Collins’s “Good to Great.”

“I knew I had to immerse myself in learning before I built my business, because if I didn’t, who would take me seriously? That wasn’t a lack of self- esteem—it was a fact,” she writes. “I didn’t have an M.B.A. or a Ph.D. in business; I had never even worked in a corporation. I was a philosophy major as an undergrad and had a graduate degree in theology.”

“Part of playing the long game is understanding that you can’t always immediately jump into the ring. Moving slow may feel like wasting time,” Clark writes. “But every moment you spend understanding the nature of the game, and how it works, makes you stronger once you do get in.”

Read: Hoping to use your IRA to start your own business? Think again

She emphasizes the importance of a network of supporters you can learn from to making a career shift. “It could be meetups or professional associations or industry conferences,” she writes. “There are plenty of ways to do it. But if you’re hoping to establish yourself in a given field, making an effort to get to know that world is key.”

“You’ll be in the dark when it comes to pricing or other sensitive topics (because strangers don’t disclose that—only friends and close colleagues do), Clark continues. “And you won’t get the opportunities you’d otherwise qualify for (because you need someone to suggest you, but you’re not on anyone’s radar). Taking the time to connect with others and immerse yourself in new communities can be a powerful way to set yourself up for success.” 

In my personal research for my books and columns, I’ve been struck by the fact that midlife entrepreneurs and career pivoters often create a series of acts when they push out of their initial linear career path. When I returned a few years later to visit the career pivoters I profiled in my book “What’s Next?,” for example, more than a third had moved on to other ventures. They had sold their businesses or added a newer one, starting over once again with gusto.

That’s why this nugget from Clark’s book rang true to me: “The most successful people enjoy their success, then recognize: it’s time to move on and learn something new,” she writes. “Playing the long game means understanding where you are in the game and ensure that you don’t stop and don’t stagnate. That’s how you win. Don’t stop learning. Soon, it’ll be time to start the cycle over again.”

Dorie Clark’s advice for older career switchers

I thoroughly enjoyed reading Clark’s new book, and I suspect you will, but I wanted a little more, so I asked Clark to share her advice with me (and you) specifically for workers over 50 and midlife entrepreneurs, starting a second act. Here you go:

Calibrate your comparisons. It’s easy to get frustrated when progress doesn’t come as fast as we want it to. Especially if you’re comparing yourself to colleagues who have spent years in the profession you’re now entering, it may feel like you’re incredibly far behind.

It’s important to calibrate your comparisons. They may have more experience or connections in your new field, but you haven’t wasted the years you spent on other things — you’ve been cultivating knowledge and experience they don’t have. You have advantages, too, and it’s important to remember that. 

Extend your runway. One of the best ways to take pressure off when you’re making a career change or launching an entrepreneurial venture is to ‘extend your runway’ and explore it part-time until you get a clearer sense of ‘product/market fit’ — i.e., what customers will actually pay for. The more time you give yourself, the easier it is to replace your current income level and make a transition without experiencing a drop-off in quality of life, or incurring unnecessary risk. 

Look for the raindrops. It can take a while for an entrepreneurial venture or a new career direction to get off the ground. In the period before it’s clear that you’ve succeeded, it can often feel like a dark tunnel – are you making progress at all? How much longer? It can be a frustrating and discomfiting time — and that’s when so many people quit prematurely. Instead, I suggest “looking for the raindrops,” meaning to make a conscious effort to identify small signs of progress, so you can both celebrate them and validate that you’re on the right track. They might seem insignificant (“Big deal, five people signed up for my newsletter today”). But when you’re just getting started, having five more people who are interested today, as compared with zero last week, actually is a big deal — and a small piece of evidence that your message is starting to resonate.

Kerry Hannon is a leading expert and strategist on work and jobs, entrepreneurship, personal finance and etirement. Kerry is the author of more than a dozen books, including Great Pajama Jobs: Your Complete Guide to Working From Home, Never Too Old To Get Rich: The Entrepreneurs Guide To Starting a Business Mid-Life, Great Jobs for Everyone 50+, and Money Confidence. Follow her on Twitter @kerryhannon.