Secrets to success: Encore entrepreneurs talk about confidence

Encore entrepreneurs – those who start their first business after the age of 50 – have some advantages over their younger counterparts. They have gained experience in the working world, have built a network, and may have more financial resources to bootstrap a fledgling company. But the single biggest advantage, according to the 2021 Hiscox Encore Entrepreneur Report, is confidence. 

The advantage of confidence

Confidence was cited by 43% of respondents as being the biggest advantage to becoming an entrepreneur later in life. And it often stems from having had a long, successful career in a given field. 

John Mattson worked in university and other career centers throughout his career. He founded Career Coach Consultants because he was approaching retirement, but didn’t want to stop working. He said, “I was facing my retirement, but I said to myself, ‘I really don’t want to retire.’ So I’m going to call this period my un-retirement and see what that is like. I don’t think I’ve ever worked a day in my life because I’ve enjoyed my career so much.”

John’s confidence in his abilities as a career counselor, as well as the network he developed over the years, gave him the confidence to go out on his own. 

“I have every single business card of every person I’ve ever met in my life,” John said. And I think I’m up to 1200 contacts on my LinkedIn account. I can call people up and say, ‘I’ve got this client I’m working with. Would you be able to give me some advice as to exactly what they need to do and who they need to contact at a certain company?’ I try not to abuse my contacts too frequently, but it is helpful to have them.” 

Related: When is the ‘right’ time to start a business? 

Know what you don’t know

Thana Sakas, founder of Gramercy Consulting in Atlanta, knows that confidence sometimes means knowing what you don’t know – or don’t like -  and knowing you don’t have to do it all. 

“A good piece of advice is to have a growth mentality and think in terms of abundance,” said Thana. “I think my business has been so successful because I had the courage to pay somebody to do the things I don’t want to do, so I can spend my time doing more business development and the actual delivery of the services that I do.”

Confidence can be built by starting out small, while you’re still working for someone else. “I’ve told people who want to start a business that it would be very useful if you started that business on somebody else’s dime for a period of at least six months to a year and see how you like it,” said John. “And I think it is important to try to learn from others who are doing the same work that you want to do, and then to segue off into your own business. Don’t just see something and say, ‘I want to do that.’”

Confidence pays off

Having the confidence that comes from years of working experience is paying off for encore entrepreneurs. Just under half (45%) of those surveyed said they expected to earn more money working for themselves than they made at their last full-time job as an employee. Over two-thirds (68%) went on to do so. It took an average of about two years to reach that level, however. The effects of confidence can be surprising. According to Thana, the thing that surprised her the most was, “the pure joy that comes from creating a job that is the perfect intersection between what you’re really, really good at and what you love to do. It’s like the dream job.”

Do you have a business dream? Tell us about it and your business could be featured on our blog and social media.