Leaving Ain’t Easy

Gareth I. Jones
7 min readApr 24, 2023


When you finally exit your company you might expect a wave of relief or a sense of elation. The reality might need you to be a bit more prepared.

Photo by Manki Kim on Unsplash

If you’re pitching for investment, or going through an accelerator, you’re highly likely to hear that question of “what’s your exit strategy?”

I’ve written before about how much I hate this question, but if you actually go through the exit process then you might find yourself facing some really complicated feelings.

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For something that can create so much stress and pressure, the idea of that responsibility moving away can seem quite attractive when you’re in the midst of another disaster or leap of faith.

The fabled exit promises richness, success, validation, everything that every entrepreneur could possibly dream of.


But the feelings afterwards are like any major break up. I’ve written before about how choosing your co-founder is like picking a life partner, so the thing you create together and then choose to leave is not a lightly taken decision.

Like a divorce, or break up you have to process it and come to terms.

I was recently at a breakfast workshop where one founder described it as actually being more painful and difficult than his actual divorce.

This seems to be coming up quite a lot right now, to the extent where I wonder if after getting through the last couple of years people are questioning whether they have the fuel in the tank to go through it all again.

There’s a bit more depth in this around the age and stage at which you decide to exit.

Sometimes you can map it out, you reach a certain level and decide that’s the milestone to bow out at. It might be a sense of your skillset and whether you fit better at a different phase, it might be about your feeling of “mission complete” when you gain market validation or another key objective.

But when you’re out, you’re out. You are unemployed overnight.

This is one of the hardest things to deal with for people with the drive and determination needed to make a business a success from scratch.

Depending on how amicable the exit was — and who it was to — you might have non-competes in your contract or other restrictions on what you do next.

If you are in a niche industry, that can be even harder. If you’ve become a perceived leader in that world then you might have opportunities but not have the ability to take them.

You lose something that is both your livelihood and identity.

If you exit the business in your 30s, 40s, or 50s, you might still have decades left in your career. You likely have a high work ethic and have no desire to retire.

You don’t want to start at the ground floor in a new industry and lose all of the compound value built up to this point.

Even if you choose to retire, I can near guarantee that you will want to get back into the mix within a month. Being in the mix can be addictive, it can feel like a sport.

But it is also likely your identity. I talked about this in a previous post but similar to the Smiths, Butlers, Millers, and Gardeners of the world, people will quite likely associate you with your company or role when identifying you. I was Gareth Ice for a long time, now I’m Gareth Town Square.

I am leaving you

One other aspect in this is the group of people you leave behind. If you’ve been building a team then chances are you’ve been as methodical and intentional in that process as much — if not way more so — than any other aspect of growing your business. Your people are such a vital element.

If you just leave one day, you leave the joy (hopefully) of working with this gathered crew. You leave all the trust, faith, and experience developed over years of taking on big hairy challenges that felt insurmountable.

That tribe mentality that you build is something else.

One thing I did after the ICE exit was write a list of people I would want to work with in the future, and a lot of those names were people we had built up in our team.

But I also kept asking myself “is that fair?” You want that team to thrive in your absence (assuming it is amicable and the non-competes aren’t too threatening) and picking it apart can be detrimental to that aim.

It’s quite a useful task to take a piece of paper and write that out. I wrote about this a bit in a recent post on building your network, but if you’re ever sat in a coffee shop waiting for someone to turn up, take out a blank piece of paper and write out a list of people you’d love to work with or create something with one day. It doesn’t have to be realistic, or sensible, but as with everything it can help you to understand you better.

Why are they doing that?

When there’s a bit of breathing room, and the dust has settled, you’ll start to see strange things happen with your old company.

The entropy of decision making plays out in front of you, and at times it can be very hard to process and deal with.

Why are they doing things this way? What possessed them to fire that person? How could they choose this rebrand? Why did they ditch that product line? How have they lost that key client already?

You might do a thorough handover, but it is very difficult to handover values and intrinsic motives.

When you make a decision in your business, you’re making it on a mountain of other decisions you’ve made in the past. Some of this might be sunk cost fallacy, some of it might be trying to stay consistent, there might be a big dollop of ego in the mix.

You might be right, you might see things through the pain and suffering that guides you well when it comes to future decision making.

There’s probably a separate post on this, but one thing we say to new recruits as part of our “way we do things around here” induction bits is that just because we’ve tried something before and it failed, that doesn’t mean we don’t try again. You just have to learn your lessons.

If you’ve tried something that didn’t quite work out, it’s on you to decide if it would always fail or whether you need to identify how to tweak it to make it fit.

You don’t see all of everyone else’s experiences. You can’t possibly fully see it from their perspective.

Going back

I think in this, there’s a lot of evidence as to why founders so frequently go back. It might be a lot of nostalgia, but it might just be irresistible.

When you see how it is after you’ve departed, and you can see the potential of where it could get back to, then there can be a real pull.

There’s something else to this, which I put down to just taking a rest and getting some distance.

Having a bit of time out of the business can give perspective, can allow you to catch your breath, and rebuild reserves to go again.

To that end, I’d suggest rethinking whether you want to exit, or whether you just need to take a sabbatical and rediscover why you care so much about what it is that you chose to do with your life.

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Bonus Content!

For this post, I decided to ask ChatGPT for 500 words on this topic. It was heartbreaking how quickly it outperformed me, but I’m getting over it.

Leaving a business that you have created can be a challenging experience for many entrepreneurs. Entrepreneurs often pour their heart and soul into their businesses, and leaving it can be emotionally difficult. Moreover, leaving a business can also impact the entrepreneur’s wellbeing in many ways.

One of the biggest emotional challenges entrepreneurs face when leaving a business is a sense of loss. Entrepreneurs may feel a strong attachment to the business they have built, and leaving it can feel like they are leaving behind a part of themselves. The business may have been the source of their identity, and they may feel a sense of emptiness as they adjust to life without it.

Another emotional challenge is the fear of the unknown. Entrepreneurs may worry about what their life will be like after leaving their business. They may also be concerned about their financial stability, as the business may have been their primary source of income. This fear of the unknown can lead to feelings of anxiety and stress.

Entrepreneurs may also experience feelings of guilt when leaving their business. They may feel like they are abandoning the people who have been part of their business, such as employees and customers. They may also feel like they are letting down their investors and stakeholders.

In addition to emotional challenges, entrepreneurs may also face wellbeing challenges when leaving a business. The stress and anxiety of leaving a business can have a negative impact on their mental and physical health. Entrepreneurs may struggle with depression and feelings of hopelessness, and they may also experience physical symptoms such as headaches, fatigue, and sleep disturbances.

The transition from being an entrepreneur to being a non-entrepreneur can also be difficult for some entrepreneurs. They may feel like they have lost their purpose and direction in life, and they may struggle to find new ways to express their creativity and entrepreneurial spirit. This can lead to feelings of boredom and dissatisfaction.

Moreover, entrepreneurs may also struggle with the financial impact of leaving a business. They may worry about how they will pay their bills and support themselves and their families. They may also worry about the financial impact on their future, as they transition from being a business owner to being a non-entrepreneur.

In conclusion, leaving a business that you have created can be a challenging experience that can impact both the emotional and wellbeing of entrepreneurs. Entrepreneurs may experience a sense of loss, fear of the unknown, guilt, stress, anxiety, depression, and financial difficulties. It is important for entrepreneurs to take care of their emotional and wellbeing during this transition, and to seek support from friends, family, and professionals if needed.



Gareth I. Jones

Founder of TownSq, focused on building communities of entrepreneurs, supporting startups and B Corps - businesses that are better for the planet.