Life after a business exit: Why and how founders should prepare now

June 27, 2022

Written by Monique Borst, entrepreneur and advisor guiding founders and change makers on the parallel track of building, scaling and funding their vision, and growing themselves.


What do you do with the time you have now? How do you infuse your soon to be newly free time and life with purpose and empathy?

The after-the-exit experience is a subject area that is rarely talked about.

In part because it can be very difficult for Founders to vocalize that they’re finding it challenging to adjust after a sudden influx of wealth. It also goes against what we are taught to think and live for as an entrepreneur: build to an exit and it will rain cash forever.

But the transition challenge is real, the sudden lifestyle change that comes with letting go is both an abrupt stop and a fast new learning curve, and the reality is often quite different to the perception, your own as well as others’.

An experience filled with questions, reflection and silence as you face ‘what is it I really want to do with my life now that I have financial freedom?’

It’s a challenge you’re probably not prepared for … and you should be.

Whether you stay on in an advisory capacity post-transaction, maintain a presence on boards, become an angel investor, coast on your savings on a beach in Thailand, donate your business savvy to help non-profits make the world a better place or write a book, life after your final entrepreneurial exit can be whatever you want it to be.

You can do anything, and for some Founders, anything is the most frightening possibility of all.

Here are three areas of focus, questions and considerations, I believe all entrepreneurs must think about when approaching an exit.


Adjustment: Give yourself the same attention you would give a promising new venture

The one thing most Founders don’t give themselves is time to just sit and think. It’s a classic entrepreneur default, used to a business culture that is ‘go go go’.

You would never invest in a company you didn’t vet thoroughly beforehand. Why start working toward a new life before taking time to understand what that life might look like?

You may feel that you have to hurry, but life post-exit doesn’t move as quickly as you were used to. Take time to breathe and think about the things that really matter to you. Consider how much time you have available, how much of that time you want to spend on new ventures, and which parts of your life you’d rather leave in the past.

Avoid filling your time so you don’t have to answer that fundamental question: ‘what do I really want?’.

Be OK doing nothing. Be patient, be led by your deeper motivations, and then create focus.


Understand your work orientation

In my experience, Founders orient to their work as entrepreneurs in primarily two ways.

Those with a self-fortifying orientation focus on themselves and their ideas, they are motivated to achieve personal benefits such as money, learning, and ego gratification, and they view business primarily as a vehicle to get their ideas into the world.

In contrast, with a stewarding founder orientation, Founders are more socially focused, they are motivated by the team journey and having a positive impact on the world, and view business as an important entity worth sustaining.

These different orientations shape how founders psychologically experience and disengage post exit.

For Founders with a self-fortifying orientation it is a process of becoming, whereas for Founders with a stewarding orientation it is a process of unbecoming.

Importantly, these different disengagement paths impact how and when Founders start the next chapter of their lives.


Downsize your options before you choose

Successful exits come with wealth, perhaps more than you know how to use. Instead of allocating half your money to angel investments and riding the wave, see what your life looks like on a tighter budget. You may discover that you don’t need as much as you think.

‘The first thing I did was to leave it alone!’ one Founder told me. ‘I didn’t believe the money was really mine or if there was a hold period where people could take it back. It took 6 months before I truly felt safe, and by that time, the initial excitement had passed and I was able to think more strategically.’


Learning: Surround yourself with people who inspire new growth

Running a business is a dynamic experience that teaches you lessons every day. How you will plug the stimulation gap and continue your journey of lifelong learning?

Many entrepreneurs overlook the psychological benefits of their business, particularly the sense of community and purpose.

As the emails dry up, and the phone stops ringing, you need to build a new network.

If you find that local groups, non-profits or your private members club don’t scratch the itch, consider teaming up with other former business leaders. Look into mentorship at a start-up accelerator, where you can potentially find new investments while practicing your entrepreneurial craft.


Legacy: Winning is different this time

And the most important lesson of all? Legacy.

Winning means something very different the second, third, or tenth time around. The requirement for financial freedom is no longer a key driver. That creates an opportunity to reflect on what you’ve built so far and use your position to fulfil yourself beyond making money. If you’re not quite satisfied, or you feel there’s more to do, you now have the time and means to do something about it.

And a final message: embrace the unknown.

No matter what you do next, you are in charge of your own legacy. Look forward to uncertainty, to being able to navigate, but not plain-sail, to find out what you are capable of doing. You are still in charge of the ship of your life and you can take it wherever you want it to go.

But it is not a journey that any Founder should have to face alone. Navigating those early months can be an unsettling period for anyone, and the challenges of new wealth, taking the next steps and finding your calling are huge life decisions.


Further Information

Monique is a multi-hyphenate with a background in retail, wellness and hospitality who’s navigated her way from a full-time Managing Director role, to founder of a pioneering food delivery business and food education programme, to a trusted advisor, consultant, and coach. She partners with growth-oriented individuals, teams and organisations seeking real change in the way they and their employees think, improve leadership, agility, resilience and the bottom line, and ultimately flatten the learning curve and minimise risk for investors. Monique knows first-hand the challenges and blocks her clients are facing because she, and the 100+ leaders she has worked with, have experienced them too and the impact they’ll be having, in business and personally.

Monique is interested in how the quality of our relationships shapes the quality of our lives, and she draws on the latest findings in psychology, consumer behaviour and neuroscience. Monique writes about re-imagining leadership in ‘Leadership Squared’ on Substack and is in demand as a speaker and a regular media contributor.

You can contact Monique via her website or on LinkedIn.

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