I Want to be an Entrepreneur — Someone Let my Brain Know

I’m excited about my new career, about change. My brain hasn’t caught up and is not letting me sleep…


Garry Lee

3 years ago | 5 min read

Photo by Alysha Rosly on Unsplash

After 6 years as CEO of a company I worked 19 years for, I left to start something new. The first 5 months since making that announcement have not been what I expected. I’ve suffered from anxiety, I’ve had massive highs and I’ve struggled to make people understand why I quit the big corporate role for such uncertainty. But one thing is consistent, I am still glad I made the decision.

To understand the context of what followed, let me summarise why I left.

  • I needed change
  • I wanted to work with businesses where I could make an impact
  • I wanted total control on my working life
  • I wanted to build something with someone
  • I needed change…

I don’t repeat the point about change for dramatic effect (ok, maybe a little) but it’s the single biggest reason I left and it’s critical to understand when discussing my biggest emotion from making this career change

Photo by Ian on Unsplash
Photo by Ian on Unsplash

I lost count very early on the number of times I questioned if this was the right decision. To this day, I wonder if I hadn’t committed to both my old business and my new business partner, I might have gone back on the decision. That sounds mad, even to me, considering how adamant I was that I needed change. But there is a big difference between needing change and getting it. Walking away from a consistent and stable work life and in particular, the consistent pay is not easy. Don’t get me wrong, in the early days of RedEye we were never very secure and I told myself that I’d been through the early stages of a start-up before, so I knew what I was walking into.

But I quickly realised the difference between early-stage RedEye and my new venture — I now had a family.

I was with my wife back then, but we were not living together, we were not married, we didn’t have a mortgage and we certainly didn’t have 2 lovely children! A family puts a completely different pressure on you. When you are setting up a new business, finances are not guaranteed (particularly as I’m determined to do this bootstrapped) and you start to question all the little things you took for granted in your normal, salaried job. My wife has been amazingly supportive during this process, she’s the one that told me I needed to make the change(!) but it’s fair to say it puts new pressure on us that has never been there before and led to disagreements that I’d never have expected. And it has really all been on me. The early stages of a start-up change your outlook. It makes you look at money differently. Mentally you start looking at anything long term differently.

A Different Kind of Stress

Running a business with over 100 employees, whom I always felt personally responsible for, was a stressful experience but setting up something new is a different mental state. I don’t think I can say its more or less stressful, but I can say it is a new type of stress.

You replace worrying about other people’s livelihoods with concerns about doing everything, about ensuring you are getting through that long list of ideas/tasks because when you startup, you have 101 ideas and they generate 1001 tasks and you worry that if you don’t do every single one of them, you are blowing this opportunity.

And I think that is the new stress - not making the most of this opportunity.

For so many (myself included) you spend so much time thinking what you’d do if you set up your own business, that when you finally do it, you put the pressure on yourself to be constantly working, that any time not spent working you are cheating this vision you set yourself.

This is the thing I’ve struggled with the most since starting on my journey and something anyone going down this route needs to prepare themselves for. The constant feeling that you have to be working all the time. Someone on a forum recently asked the question to a group of entrepreneurs, how do you manage the work-life balance — the unanimous reaction was ‘it doesn’t exist, there is no balance!’. If you enter this journey, you need to realise that to make it work, there is no substitute for hard work and you will constantly be thinking about work. But personally, I’ve recently found that better balance by planning time away, by building the ‘life’ part of the equation into my working day — where the working day is the whole day in reality. For me, time with the family, reading, writing, building Lego(!) are examples of things that give me that balance. Everyone will have to find what the balance is for their life.

Photo by Matthew Sleeper on Unsplash
Photo by Matthew Sleeper on Unsplash

A Problem Shared

Whilst I don’t have employees anymore, the one person my decisions do affect is my new business partner, but this has a positive emotional impact. Having someone to share this with is the best thing about my new adventure. For years as the ‘boss’ reporting to the board, you struggle for that emotional contact and support that everyone needs. I had good mentors and colleagues but ultimately you rely on yourself more than is healthy at times. With my new venture, I’m able to openly discuss the concerns, the joys and everything involved in getting started with someone that’s as invested in this as me. He’s someone I have known for several years now and we have a similar ‘why’ for our business. We certainly bring very different skills, alternative ways of working and ideas on how to launch the business, but because we share a passion and want the same end goal, we can collaborate so well.

Mentally Switched on — Always

For some time, I always had the thought that when I left RedEye I would give myself at least 3 months without doing anything. Time to recharge and then be ready to start the next thing. That has NOT happened. I would say its for 3 reasons

  • The idea for this new business — I got talking to my friend and we both quickly realised we had a passion for the same thing and the idea snowballed
  • A global pandemic — No ability to travel to new places, homeschooling and my wife permanently working at home, meant the ‘break’ I imagined wasn’t going to be possible
  • Despite being able to afford the break, psychologically I couldn’t entertain not earning…

That last point is the last thing I expected, possibly the biggest surprise of this whole process. I’m a logical person. I’m a detailed planner. I manage my finances to the nth degree. So I knew I didn’t need a paying job yet. I knew how long I had before I needed to start earning. But none of that mattered in the end. My mind would wake me up in the middle of the night, asking why I wasn’t earning. I’d be networking, meeting new people, writing stories, generally making the most of free time to interact in interesting ways — but at the back of my mind that nagging feeling kept asking why I wasn’t earning a living, that all these things weren’t a ‘real’ job!

And I think that’s the massive learning curve for any entrepreneur, start-up, business owner — anyone that’s doing something different from a regular job, that you have to get used to uncertainty. Success will only come by trying new things. It will come from being brave. It will come from change. It will only come from making mistakes. I just wish someone would explain that to my mind, so he could stop worrying and let me get some better sleep!


Created by

Garry Lee







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