Decision Making Self Care

Something Is Missing

Six months ago I sold my business. 

I started the business when I was 22 and sold it 7 years later, a couple of months before turning 30.

Running the business was pretty much all I knew in my 20s.

It’s where I spent virtually all of my time. Days, nights, weekends. I was obsessed. I cared for it more than anything. Perhaps too much. 

At times, my identity was so tied to the success of the business that it became unhealthy. If the business had a bad period, I would feel awful — at one point falling into a deep depression for many months.

In the last couple of years, I tried to move my identity away from the business.

I would be “Anthony the CEO” not “Anthony the founder”.

I was playing a role in the company now, not the parent.

And this definitely helped.

It took time for my identity to slowly shift. And in the months leading up to the sale, I was pretty removed from the day to day operations of the business. This was by design — we had set up the company so that it could run without me — but also because internally I felt I needed to separate myself.

When the opportunity was there to sell, I took it.

I felt that this chapter of my life had run its course, I’d learned everything I wanted from it, and it was time to move on. Selling the business would be the final chapter and I’d be able to close the book on “Anthony, the founder”.

For the first few months, I felt amazing. I was able to walk away from the business right away, and I moved from New York City to Miami.

I rented a beachfront apartment and woke up to the sounds of waves hitting the sand each day.

I had zero responsibilities — no employees, no business, nothing.

And I had enough money now to not need to work for at least a decade.

Sounds like a dream right?

Well, it’s been about six months now.

And something I didn’t expect started to happen.

I started getting a bit depressed. But I had no idea why. 

I have zero responsibilities and zero money issues. 

When I was a kid, I thought these would make me the happiest person around.

So then I got to thinking and really started to examine why I was feeling this way because it didn’t make any sense.

And I started doing some research.

What I found was fascinating.

One article I came across was called “Dealing with the Emotional Fallout of Selling Your Business” by Jeff Giesea, published in the Harvard Business Review.

The article starts like this ‘“Congrats on selling your business,” a longtime mentor said the day after I signed the paperwork. “Now get ready for a depression.”’

He goes on to say how entrepreneurs who have sold their businesses often feel “isolation, a lack of purpose, a sense of drift. It seems obvious in retrospect. When you spend years architecting your life around business and suddenly it’s gone, you’re probably going to have an identity crisis and some post-partum depression.

Then there’s the issue of purpose and motivation. Without the constraints of money and responsibilities of your business, what will be your ‘reasons to keep trying’…The freedom of being unanchored sounds great, but it comes with the potential of drift and lack of motivation.”

This was speaking to me.

Without the responsibilities of the business or any real worry for money, I was lacking any motivation to really do anything. 

I no longer had a reason or purpose to do anything.

So I started spending hours and hours watching TV. Which is something I pretty much never did when I had the business. But I needed to fill time, so that’s what I did.

The article goes on to say “When selling your business, it’s natural to think of other major life changes to make — like moving to Montana or buying a new home. Selling and leaving your company is enough to change to handle at once.”


This was literally what I did.

Turns out I’m not alone, which is nice.

In retrospect, I might have rushed all these changes. I shifted my identity so quickly and drastically, I’m not sure I was able to fully process it.

And 6 months later, it hit me.

That feeling of “something is missing” started to make sense.

A report called “Life After an Exit: How Entrepreneurs Transition to the Next Stage” summed it up well “the reality of selling a venture often represents a loss of identity and community.”

I started to miss the team and leading people. I missed the day to day interactions. I missed the challenges, the problem-solving. I missed having a company. I missed having a purpose that drove me every day for years.

And so now I realize and admit, something is missing.

It seems obvious now that I’m writing this. 

Something that made up such a part of my life for 7 years was gone. 

And without anything to take up its place, it makes sense that something is missing.

I’m missing a greater purpose, meaning, and community that I had with my last business.

I’m not sure what I’m going to do moving forward, but I think this is a step in the right direction.

Before you can make a change, you must identify the problem. 

So, this is me identifying the problem.

And now I’m going to work towards solving it.