Entrepreneur to employee
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Entrepreneur to employee: How to make the change

12 Dec 2016

Starting your own business is tough. Making it a success is tougher. So, surely for a successful entrepreneur, going back into the working world as a regular employee should be a piece of cake, right?

Nicola O’Sullivan is an entrepreneur. She developed the idea for ExerWise, a wearable activity tracker for children between the ages of four and 12 that encourages them to be more physically active, in her final year of college.

“We got accepted into Startlab and a variety of start-up programmes. In May 2016, we completed a successful crowdfunding campaign, becoming one of 16 Irish tech companies to successfully run a Kickstarter campaign. However, due to a number of reasons, we have decided to move on from ExerWise.”

After moving on from her business, O’Sullivan wanted to re-enter the working world as an employee. Given her experience, a starting or graduate position would not necessarily be the right fit, but she struggled to find what would be right for her.

She’s not alone.

There are plenty of employees out there who fancy being their own boss some day. There are plenty of others who never really thought about the business side before, but are passionate about an idea they have.

We’ve all heard success stories of all types of entrepreneurs, from those who created multinational corporations to those who built small, local businesses that allow them the freedom and control to do what they really want.

Deciding to make the move

But what about the entrepreneurs who come full circle? Is it difficult for them to find their place in the working world once again after they’ve been their own boss?

Eleanor Harding is now a product designer for Twitter. However, before that, she founded Rigby/Rose, her own product development consultancy.

“I worked on building impactful emerging technologies that enabled people. And I was happy,” said Harding. “Soon after, my company was offered a contract with Twitter. It was right in line with the people-enabling technologies I was interested in and so I jumped on board.”

That was back in May of this year. Harding was slowly transitioning from external consulting to working more closely with a team. Eventually, Twitter offered her a full-time position with the company.

‘I really wanted to be sure that I was making the right choice in the long term’


“This was not a decision I took lightly,” she said. “It would mean winding down my company and giving up that magnificently enticing idea of being a founder (at least for now).”

Harding took two months to make the decision. “I really wanted to be sure that I was making the right choice in the long term. Ultimately, I focused on my ‘North Star’ – the thing that I care most about and the reason I love working in technology – and asked myself a simple question with a difficult answer: ‘Will this take me a step closer to that or further away?’. I deeply care about enabling people through technology and in the end decided that this position gave me the opportunity to do exactly that.”

Harding said one of the biggest difficulties about transitioning from entrepreneur to employee is the stigma of losing freedom, or the idea of suddenly having to start following orders when you’re used to being your own boss.

“These are rather terrifying thoughts and enough to put a lot of people off before they even consider the idea. For some teams, this is true. But for many others, it isn’t.”

She said a lot of it depends on the culture of the team you’re considering joining. It’s important for those making the transition to talk to your potential new employer about these concerns. “I brought my expectations to the table and spoke clearly about how I do my best work and if that would fit in with the team I would be joining.”

For those going back to work as an employee after being an entrepreneur, Harding says making sure you know what you really want from your career is paramount.

“I decided that my North Star was the idea of enabling people through technology. And if I mapped my career out into a diagram, I could see that some things had taken me closer to that, while others had taken me further away. By drawing this out and really thinking through which direction this next step would take me, I could make a genuine decision that I would be happy with.”

Once you’re comfortable making the move from entrepreneur to employee, it can be a wonderful transition when you’re headhunted or offered a job because your entrepreneurial skills have been recognised.

Putting your best self out there

But for those who are making the decision to switch without an offer on the table, there can be other struggles they need to watch out for. Career coach Jane Downes talked to Siliconrepublic.com about what obstacles entrepreneurs might face from employers.

“The typical question in an employer’s mind is: ‘Is this person now capable of being managed?’. As a business owner, you are answerable to your clients, your bank manager etc so there is still an accountability.”

Downes also said there is a worry from an employer’s perspective about the ability to be a team player. “Go back to previous experience to highlight this and remember to highlight any teamwork or associate work you did with other businesses in your role as entrepreneur.”

So what steps can an entrepreneur take to ensure they are still very employable after running their own business?

‘It is not a black mark on you that will follow you around for ever. By doing what you have done demonstrates you have bravery and valour’


Ensure your story is straight on why you want to make the move back to being an employee. “You may be uncomfortable with managing your story for why you have gone back in-house,” said Downes. “If your business didn’t get the traction or success you had anticipated, it is your job to ensure you are comfortable with this and discuss the very relevant skills you gained in dealing with constrained resources, problem-solving and business bottom line.”

She said it’s important to remember that an unsuccessful business is not a black mark against you. “By doing what you have done demonstrates you have bravery and valour. This is a behaviour which counts in the 21st century workplace.”

Downes also advises transitioning entrepreneurs to show how your skills are transferable and to demonstrate your passion and commitment to the company you want to work for. “Have examples and evidence ready to show you are comfortable being answerable to others.”

Finally, Downes also reiterated Harding’s words of wisdom, saying that it’s important to know what you want in your career plan to ensure you’re making the right decision. “Know what you want next and build a clear career plan.”

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Jenny Darmody
By Jenny Darmody

Jenny Darmody became the editor of Silicon Republic in 2023, having worked as the deputy editor since February 2020. When she’s not writing about the science and tech industry, she’s writing short stories and attempting novels. She continuously buys more books than she can read in a lifetime and pretty stationery is her kryptonite. She also believes seagulls to be the root of all evil and her baking is the stuff of legends.

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