3 Challenges You May Not Expect When Exiting Your Business or Retiring

Phil Hendry13/10/2020

Its come to the time you have no doubt been imagining for some time….you’re selling your business, or you are retiring from a long career…..great! Assuming you have planned properly, money is not holding you back, and you now have all the time in the world to relax and do those things you had always planned. 


But what are those things?  You have spent so much time focusing on your business or career, you haven’t really thought about it or found other ways to spend your time you find as meaningful.

This is a pretty common scenario, but one that can and should be avoided.  Not the selling your business or retiring part obviously, but not thinking passed your life in your business or career.  This has often proven to be the biggest challenge for individuals in this position when they do eventually stop.  There is this void, which no matter how much golf or travelling you do, you just can’t fill.

So we think there are ways to think ahead to avoid this, with the 3 main themes being as follows:


While growing a business or enjoying a long successful career, goal setting and targets are an every day feature of life.  Often you begin to thrive off the back of constantly reaching for the next revenue target or role, which is an underlying key to giving us all purpose.  When you have reached the ultimate goal, often selling your business or not having to work another day in your life…..what comes next?

You should take this habit from your work life into your personal life, continue to set goals, and once you reach them, set more.  This can be things such as seeing your grandchildren once a week, going to concerts, attending big sports events, studying, whatever you take most enjoyment out of.  The key is articulating this, writing it down, and continuing to challenge yourself. 

This may seem arduous, but for goal focused individuals, we have seen it work really well.  Setting short and medium term goals which you can achieve is a fundamental part of what makes us happy as humans, and I’m sure we all expect to be happy when we don’t have to worry about money anymore.

Another key point is that not everyone is ready to walk away, and if you love what you do (or did), why stop.  It may be more about balancing family and work better than you have been able to before.  So look for those consultancy roles, help small businesses who would value you experience, or just simply transition more slowly while you develop a feel for life after your career.


An evolutionary need for us humans is to have a tribe, a group of people with common interests and purpose.  Within your team in your business or work, you automatically have this, but in a fairly short space of time, they’re gone.  Yes you keep in touch with some of your former colleagues, but even then without the business or company at the core of your relationship, it’s not quite the same.  For some, there is a need to constantly expand your tribe.

As you begin to understand how you can spend your time most meaningfully, you will naturally be able to find your new tribe.  This might be working with a number of small business owners offering your advice, it could be sitting on the committee of a charity, or even coaching a sports team.  If you make the effort to find what gives you purpose, you will find your tribe.


You may be used to getting up every morning, prior to heading off to your business, company or firing up the laptop in your home office, but now this is gone.  Your business and career gave you a structure to your days, weeks and months.  Now you seem to have all the time in the world, and no structure.  So you feel lost.  But one thing we cant get more of is time, so you need to create structure to give yourself energy and focus to be as active as possible, as ultimately when people reflect this tends to be what they take most enjoyment out of.

On a more micro level than purpose, try to organise your week so that you create a new structure around things like exercise, reading, seeing your family, hobbies…without being too rigid.  This sense of structure is comforting and makes you utilise your time most meaningfully. 

Ultimately, life is not a rehearsal and we won’t get time back, so instead of not thinking ahead and spending 2-3 years trying to adjust to life when you have sold your business or ended your career, plan ahead so you make the most of the time you will have.