Why do I feel so down after selling my business?

Dear Aunty B,

I sold my business six months ago and I know this is strange as most entrepreneurs are happy to leave, but I felt I was selling the business just as it was realising the potential of the past five years of very hard work.

I assumed I would stay on for a few months as part of a handover but was told that the day of settlement was my last day and, after a shockingly quick goodbye to my staff, I was out the door.

I sold for a lot of money and instead of feeling on top of the world I can hardly get myself out of bed. I start each day with a list of things to do, which is what I have always done and, instead, I feel so tired. I also feel stupidly guilty as everyone assumes I should be on top of the world and so I tell them how happy I am when I am miserable.

I am trying to look at investing in other businesses, but I just don’t feel enthusiastic even though I think there might be a good opportunity. My wife thinks I need a job, but the idea of working for anyone else is just an anathema even if they would have me.

Aunty, any ideas from the entrepreneurs you know about how to handle life post the business?

Don’t want to move on,





Dear SA,

So, here you are, a grown man and what did you do when your business got stuck? Huh? You got help. You called in experts; you came up with strategies – and not to distract you from the problem – but to deal with the problem.

So I can’t work out why you haven’t sought help on this. In other words, you don’t need a job. You need a shrink. Go and find a good psychologist and download to them. I am sure you won’t need many sessions to put your finger on what this loss means to you and why you are reacting to it in such a way.

At the same time, whether you feel like it or not, you will exercise every day: At the same time, in the morning.

Thirdly, you are going to take up something you have never done before, like planting an organic veggie patch; or taking a cooking class and cooking for your family at night; or planning an off the track holiday. Do a little bit each day, but make sure it is something where you can see results.

Lastly, you are going to change the way you think. Focusing on your mental and physical health for a few months after building a business for five years is an extremely worthwhile thing to do. It is also a great reward.

And it doesn’t mean you are not going to do stuff for the rest of your life. It just means you are focusing on a few different parts of yourself for a small period of time.

If you do this then the answers will slowly come to you and you will see the opportunities that start to present themselves. Making sure you have small creative outlets will go some way to assuage that powerful urge you still have to build and create.


Be smart,

Your Aunty B


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