When is the ‘right’ time to start a business? Advantages to waiting until after 50

Many people have a dream of starting a business of their own – being their own boss, doing things their way. But somehow the time never seems right. Early on, you may not feel you have the necessary experience. Before long, you may have responsibilities, like a mortgage and a family, that make striking out on your own seem too risky. Later, you may have so much invested in your career that it seems daunting to start all over again. 

So, is there a ‘right’ time to start a business?

There is, but it can be different for everybody. And that’s the answer in itself, because the question isn’t really, ‘When is the right time to start a business?’ It’s ‘When is the right time for me to start my business?’

The answer is a combination of many factors: your product or service, the market, and, most importantly, your motivation and confidence level. For many people, that level of confidence and motivation to succeed only comes later in life. 

Meet the encore entrepreneurs

Hiscox recently surveyed 400 small business owners who started their first business when they were 50 years old or older. The 2021 Hiscox Encore Entrepreneur Report found that nearly half (43%) of encore entrepreneurs feel that the confidence they have as a result of their age is the biggest advantage to waiting to start their business. They also cited a larger professional skillset (42%) and more industry experience (39%) as reasons they waited to take the leap. 

Why start a business after 50?

We found that the most popular reason for starting a business later in life was to pursue a personal passion, cited by 24% of respondents. But nearly as many said they did it for greater financial independence (23%) or to make more money than they were making as an employee (22%). 

Take advantage of your experience

Another advantage to having years of work experience behind you is that you don't know what you don’t know. Encore entrepreneurs may have fewer bumps in the road because of their maturity. Even still, starting a business can bring some surprises. The encore entrepreneurs who took our survey said they would have liked to have had more marketing experience (34%) and more knowledge of e-commerce fundamentals (33%) to help them as they struck out on their own. 

Testing the waters or jumping right in

The majority (60%) of encore entrepreneurs had the confidence to jump right into a new business venture, taking advantage of their experience and connections. The rest began their businesses as a side hustle, then took the leap to go full time at a later date. For those who tested the waters with a side hustle first, 54% of them were in business full time in less than a year. 

Related: Why now is a good time to start a side hustle

Protecting your business

One thing that encore entrepreneurs have learned from experience – especially recently – is to expect the unexpected. Over half of the respondents to our survey (58%) have insurance to protect their business from the financial impact of a claim or lawsuit. Another 26% plan to get business insurance in the next 12 months. 

Related: Why you need insurance coverage for your small business 

The right time to start your business

Everyone will have a different answer to the question, ‘When is the right time to start a business?’ But having the confidence and connections that can only be gained from a decades-long career working for someone else helps. When the opportunity presents itself, take it – you never know when you’ll get another chance. 

Read the full report

To learn more about how encore entrepreneurs succeed as business owners after age 50, download the 2021 Hiscox Encore Entrepreneur Report. Maybe you’ll find the inspiration you need to start your own business – no matter what age!