Exiting your business: The grief of the Founder

Coaching conversations with Founders and Exec Team are going deeper

So 2026 is proving to be just as heavy as 2025. The conversations that Founders and Senior Leaders are bringing to coaching are getting deeper and more personal all the time. These brave souls now wend their way through weighty global crises and AI transformation, all at the same time as giving birth to their business baby. The work is existential, all-encompassing, and these are big conversations, much closer to the therapeutic boundary than they used to be. We’re not discussing goals and feedback here, no no. My work as Exec Coach to Founders and C-Level leaders is whole-human, deep, edgy and tough.

Working across diverse sectors and industries, I am privileged to witness a whole host of themes, emotions and experiences that rarely make the leadership playbooks. The great big one, that I read about the least, and hear about the most, is grief.

For all the Founders who are living the dream already; those who have stopped or paused; and those who are yet to begin – please be prepared. There be some full-scale grief in them hills.

Where there is a Founder, there is grief

Whether you exit with a stack of cash in your pocket, or you lose your dream to a funding disaster, in the end, it may not protect you from a rollercoaster of emotions.
If you’re brave enough to choose the Founder's journey, you need to be ready for both a good dose of serotonin buzz, excitement and thrill, and (at least the risk of) a belly full of grief. That’s all part of the game.

This is not a reason to stop of course. If we feared loss too much, we’d never fall in love, would we. And the same applies to the entrepreneurial journey. But it's not for the faint-hearted.  Understanding the emotion involved is useful and powerful. The path of Founder can be lonely at times, and none more than when the grief hits. So let’s get talking about this taboo topic for leaders.

The excitement and energy of building your own dream cannot exist without the inherent risks to heart and mind. You know that, right. So this is the first in a pair of articles written to support your thinking in that. This one explores what we call “Exit Grief”. All the light and shade of leaving your scaling business, whether you deem it “successful” or not.

The second article will explore “Scaling Grief” when your Start-Up grows into a Scale-Up, you stick in there and the time comes to change your role and identity. Playtime is over and your baby turns awkward teen.

And so just like that, you’ll notice that whether you exit or scale, there’s a grief article, just for you. And yet it’s all still the most incredible ride and could be the journey of your life.

So here we go first: Often the most shocking and quickest twist of the plot:

Exit Grief: The emotional reality of leaving the business you founded.

This can happen for a whole host of reasons, and each of those has its own particular sting. There’s the sudden realisation in a single meeting, that the wheels have now fully come off and the game is over. I’ve coached Founders who’ve fallen out with their co-Founder and decided to leave after a single fight. Those who’ve been ousted slowly by the very Board they appointed. Some have been forced to stop due to burnout or illness. Others have been tempted away to a ‘proper job’ in a moment of financial stress or slowly realised they're not heading in the right direction. Some have recruited a key player or co-Founder and experienced their company being turned into an animal they don’t recognise or even like. Some have had their funding pulled or a pandemic bite. So many ways to lose control and lose your dream in easy steps.

And reading them in a list like this, it becomes obvious, the pain is real.

The loss of the original dream

The idea had to be strong enough to keep you awake at night, fill your every thought and sustain the plan. It must’ve been, in so many ways, a brilliant idea. One worth putting your heart and soul into. This idea was enough for you to risk your precious time, income, energy, reputation. You will have needed to believe it, and persuade others to believe it, from your partner and friends to your investors and team, for some considerable time; sometimes many years. To finally look the truth fully in the face and decide to stop believing that this idea is worth building a business and a life around, can be agony.

The loss of identity after the sale or departure from your business

This might the biggest hit of all. Being a Founder is a whole-human activity. It’s all encompassing, and for those working in any sort of scale-up, it’s a shorthand code for describing who you are. Assumptions abound about the type of person who’s a Founder. You might as well open with “I’m smart, brave and innovative”, by introducing yourself as Founder. In days gone by I used to coach retiring doctors. GPs, as we say in the UK. Community family doctors, the General Practitioner. When you ask a GP what they do, they say “I’m a GP”. They don’t say “I do GP”. Instead they ARE a GP. It is their identity and often a sudden loss of identity can accompany their retirement.

The same is true as Founder. “I am Founder of ABC company”. Not “I am founding”. So what happens when the bubble bursts and the role is no more? If I’m no longer a Founder, who and what the hell am I now? Many Founders are shocked to feel totally lost after they sell or leave their company. Every psychological model out there reminds us that we need a sense of belonging. Without it, we start to spike cortisol and mount a stress response. So leaving quickly or slowly can send us to a very lonely place. Some of the cool cat founders' clubs that fed our sense of belonging have names that make us feel excluded. Female Founders Rise and Founder Unite. Are we still allowed in or do we sit in the lobby now?

The loss of the relationships that felt like family

Often Founders leaving their role discuss the deep loss of their team and even clients. The intensity of scaling is such that the teams who are brave enough to try have spent days and nights battling problems, overcoming blocks, preparing pitches, trying to “win” in various ways. To survive any time at all there must’ve been shared successes, celebrations and stories. Out of work time, weddings are celebrated, babies are born, lives are created as they birth their start-ups together too. The relationships are not like blue chip corporation relationships. A family feeling develops. When the Founder journey is over, many of these relationships will prevail and last a lifetime, but there can be  complexity: sometimes inequality of outcome, blame, guilt, anger, sadness. Much of this will calm over time, but some might stay with people for their entire career.

In writing this article I was moved to find and read the blogs by Peter O’Malley, co-Founder of Advisable as it folded. If you’re reeling in the early days of closing your business, proceed with care. This is a really tough article about his grief for his “dead startup” and interesting that he describes one of his conscious moves to quell his pain was to invest a good deal of attention in telling everyone about the great team that they should employ.

Betrayal, let-down, disagreements in the lead team

Sometimes a crucible moment will lead to a personal divergence or clash. Trust can be tested at these moments as you’re exiting your business, and without an external guiding hand, fractures can happen which are felt truly as bereavement. Suddenly having been work and playmates for a long time, you’re at loggerheads and alone.

And the strangest feeling of all:

The Grief of Success after selling your business.

After all the raw emotion, energy and hustle, the mountain that everyone was trying to scale has been conquered and the job is done. Perhaps the funding round closes or the sale is agreed. The IPO lands or the exit happens. And it feels hugely conflicting for the Founders. You’re stepping away from your company and someone else is in charge. All the language in the press release and the internal comms describes success and celebration. So why are the Founders left breathless and confused? Even back in 2014, this article in Psychology Today outlined the conflicting sense of loss even with huge financial wins. 

Coaching support when you are exiting your business

After so many coaching conversations with Founders that return to the theme of grief, we have created some focused coaching services especially for Founders who are exiting their business. If you’re preparing for exit or are already navigating the emotional aftermath of selling or stepping away from your company, this is a moment that deserves the same care and attention that you put into starting up.

These conversations need time and space. Literal space – outdoors, in nature, unbounded by offices and artificial light. They offer a chance to really explore the journey, the highlights and the fun. To recall the brilliance and the joy, the reasons why you began. There’s also space for talking about regrets, mistakes, shocks and missteps in an environment that’s safe, non-judgemental and confidential. We can offer some tools and methods for dealing with the big stuff, and sometimes even a signpost to a great therapist.

Call it a Pilgrimage, a Retro, a Wake, a Send Off, a Celebration. Having this work designed, hosted and witnessed by a specialist trained Coach Facilitator will make a powerful difference.

We work with individuals as they exit, and also with teams. The benefit of bringing a team together to mark its ending is huge. We take great care to design the right sort of input to reflect what you’re aiming to do.

They say that great beginnings come from great endings, so it’s vital that the ending of a company’s life is done well, to free you up to go again, or not, with your broken heart healing well.

If you’re curious about your own ending to this chapter of your Founder’s journey, I’d love to speak to you about it. Help yourself here to a convenient time to get the conversation started. Or find me on Linkedin.