Should you sell or should you hold?

You have a business that’s making you good money. It’s growing, people envy you and things are rocking.

Then someone comes along and offers you a lot of money for everything – more money than you could get if you sold the business today – and makes it clear that it’s now or never (the longer you resist, the more time they have to develop far enough to move forward without you). Do you sell out?

In hypothetical situations the first answer is usually no, of course not – who would consciously want to sell when the obviously smarter decision would be to hold on to what you have and keep building it so that you can sell it for even more money down the road?

But you haven’t had, say, a 6-figures check waved under your nose lately, have you?

Money (real money) changes people. It creates openings in your mind for doubt, exaggerates it’s own value and downgrades that of your existing plans, it can change the best of people.

I used to think that ‘independence’ meant working for yourself. I’m less naive now – independence means many things, and who and what you work for is just a way of putting food on the table (leave the drama for those who have time for it). At the end of the day, the question comes down to this:

Should you cash in now or wait till the moment before it hits it’s peak (the upper limits of where it can go with you in charge) and sell then? And also, can you put in the effort to take it that far (you’ll find someone willing to buy, that’s not even a question, and if worse comes to worst, automation can be your best friend)?

Of course, the flip side is that you can be too greedy and hold on to something you can’t grow further till the point that you’ve run it into the ground and there’s no one around to clean up the mess. That can only be a concern, however, if you resist your greed for ‘more money now’ in the first place.

Should you sell or should you hold? In most cases, I’d recommend holding – unless you need the money desperately (or you’re going into a more lucrative line of business), building your assets is a better long-term strategy than selling and starting over – Thing is, selling is almost always the easier, more gratifying option.