Gen Y Speaks: I let everyone go from the startup I founded while it was still doing well. Here’s why I decided to start afresh

A good dog never growls at its owners. A good marriage means few arguments. A good business is one that is profitable and growing.
These seemed like wise adages, or so I once thought.
On one particular Monday in September, I went into the office, sat each of my employees down one-by-one, and told them that I was letting them go — not due to any fault of theirs, or because of the company’s finances.
It was hard to explain, but I needed to upend the life that I had been constructing for the past decade, even if – by most metrics – it was doing fine.
I was fortunate enough to have a comfortable childhood, and parents who were supportive of all my pursuits.
Throughout my growing years, they nurtured me the best way they knew how, by building up my confidence, telling me they were proud of me, and proclaiming me to be a natural leader.
Perhaps that was what gave me the foolhardiness to plunge into starting up a new video production business after graduating from university in 2012.
I had studied video production, and I had no doubt that I could make a living from the skills I had at the time.
Moreover, my mother had been diagnosed with cancer, and this was the best way to maximise the time I spent with her.
In 2013, my then girlfriend joined me, and over the next decade, we slowly expanded the company to a peak of 15.
Together with our team, we worked on over 400 projects for 120 clients to create corporate videos and other short-form content. We had a solid stable of clients, which enabled us to ride the waves of different challenges, including Covid-19.
In the eyes of many people, we were a company that was doing fine.
Just like how the pandemic was a time for many to reflect deeply on their lives, it was the same for us as well.
As we took a pause and relooked at what we were doing, it soon became apparent that our “good” business was perhaps not so good for us.
Running a new company is easy, insofar as the goals are straightforward — get more portfolio, clients and staff members. Rinse and repeat.
It’s hectic, and the breakneck pace means that you never stop and reflect on what you’re doing.
But when a company matures, you cannot keep doing the same. The world around you is always changing. The conditions that make you profitable today won’t exist tomorrow. The challenges you face may not be part of a cycle, but a permanent, structural change.
Being in the creative space, our strongest asset will always be people and if I wanted to grow the company, or even just survive, I needed to invest time and energy into management, culture, and establishing a deeper vision for the business.
But these were not areas that I was good at, and having never worked for someone else before, I had no reference point. Plus, I had been told that I was not a natural business leader.
Perhaps the idea of such a leader does not exist at all, but the reality was that I did not want to commit to doing what was needed to take my company further.
What I enjoyed about my work at the production house is getting to listen to the stories of people from all walks of life, and having intimate access to the inner workings of various organisations that I work with.
To me, my fulfilment did not come from running a business in itself. If I were to commit to the task of growing the company, then I would just be shackling myself to the job, and missing the point of being my own boss.
That was back in 2020. It took me close to three years to take the next steps, which was letting go of all my employees (except my wife, of course) and moving into a tiny office space, turning back the clock on a decade of work.
Perhaps I could have made the change faster if I had some deep creative hunger to fulfil. Truth is, we were ok. I wasn’t exceptionally unhappy. Our revenues were not a disaster.
The bigger problem was that I had tied my identity to being a business owner, and I was afraid to let go of that. I couldn’t envision what an alternate life would look like, and so I kept putting off what needed to be done.
But then I looked around myself and realised that many things that I hold to be self-evident truths are simply false once I thought harder about them.
A good dog never growls at its owners? Our adopted Singapore Special frequently growls at us, simply because he didn’t grow up learning any other way to communicate, but he’s not aggressive by any measure.
A good marriage means few arguments? My wife and I argue all the time, but working through disagreements helps us understand each other better. A marriage with no arguments is worse if both sides are hiding their feelings to avoid conflict.
If I could see that these truisms were not what they appeared to be, then why am I hung up on the idea that a good business is simply one that is profitable and growing? Why could I not recognise that it is possible to have a profitable company, and also that I needed to give it up?
What finally helped me to make the decision was realising that running the business was sapping my emotional energy, which is much harder to regain than physical energy.
My wife and I had no hobbies, our social circles were shrinking, and even finding the energy to watch a new television show often felt like a daunting prospect.
Ironically, even though we worked together, we never felt like we had enough time for each other because we were always in business mode.
A year after I started the business, my mother passed away.
Throughout her illness, I saw how having money enabled us to maximise her treatment options and keep her comfortable. That was the lesson I took away then, but a decade later, I realise that the more important lesson is to not waste time living a life that is just okay.
My mother died at just 56 years old; any of us could go tomorrow. If we have the privilege to do so, we owe it to ourselves to thrive, and not just survive.
There are so many more places to go, people to meet and things to try. Maybe I could shine in a different industry. Maybe I might do better as an employee than as a boss. Maybe I might produce the best work of my life working with my wife. Maybe I was wrong about it all, and will start hiring people again.
The exploration, and not the conclusion, is the main point.
As we approach 2024, I will continue to have doubts about my course of action, but my decision has unshackled my creative energies and given me the drive to do my best for projects that I feel passionate for.
I am also energised at the opportunity to work even more closely with my work and life partner, and I am thankful for the clients who continue to have faith in us and our ability to produce quality videos, even as we evolve as a company.
Most of all, I am no longer at the crossroads, and am excited to be back at the trailhead, knowing that I have the power to redefine my journey along the way.
There is value in running companies that eschew the pursuit of growth, in favour of building a path that is mentally and emotionally sustainable.
There is value in living a life where “luxury” comes from the peace of mind in knowing that you have crafted your life consciously and deliberately, even if it doesn’t turn out as planned.
Most of all, there is value in searching for a way to thrive, and not just do ok. It’s safe in the boat, but if it isn’t sailing where you want to go, then you might be better off jumping into the water and swimming.
ABOUT THE AUTHOR:
Jeremy Oh, 36, is the founder and director of video production house OHBOY! Pictures.