3 Reasons You Are Ashamed to Say, “I Want to Sell My Business”

3 Reasons You Are Ashamed to Say, “I Want to Sell My Business”

I need to get out!

That’s how Anne started the meeting.  She blurted the statement like it was an admission of some disgraceful, abhorrent, late night activity.

She was expecting me to respond with, “you should be ashamed of yourself.”  Instead I said, “that’s great.”

While I saw a vibrant, energetic, small business owner finally admitting the need to change course, she saw the statement as shouting her failure.   Anne’s business story is fabulous.  She hasn’t accomplished every goal she had for the business, but the barriers she’s overcome to start and grow her business are impressive.  Yet she, like so many of us, struggles with shame, guilt and avoidance as she considers letting go and moving on.

Why do we struggle?  Why is it so hard for small business owners to explore the option of selling their business?

#1.  We Believe Selling is Quitting

How many times did you have to overcome the temptation to quit in order to get where you are now?   Employees quit, clients quit, equipment quits working . . . everyone and everything quits except you.  The only reason you are here, the only reason your business survived, is because you refused to quit.  We teach ourselves to ignore or overcome that feeling we all share at some point that . . .

I just don’t want to do it anymore.

We fight it off, and we survive.  Now, here you are reading an article trying to make it easier for you to “quit”.

You should stop reading now, because selling is quitting.  Right?

What We Need to Understand is All Journeys End

Try these “truth bombs” on for size.

You are going to exit your business someday, and it will likely not be under ideal circumstances.  I know you have the vision of setting sail in the yacht you bought after the sale of your business, but the odds say you won’t “leave on top.

Exits are hard, but absolutely unavoidable.  At some point you’re going to have to step off the path (or be shoved off of it by circumstances).

Change is inevitable.  You will leave.  Embrace that reality.   Once you accept that truth, leaving your business becomes a question of when, not if.  Then it's really about determining the best timing.

Is it time to leave?  No? Then by all means fight on!  But if the voice in your head is constantly screaming “get out”, now might be the time to start exploring.   Don’t let the fantasy of entrepreneurial immortality keep you from making a move that offers you a better option than your current ownership slog.

Ending your relationship with your business is part of your journey with that business.  It is unescapable.  It is inevitable.  It is coming.

Embrace that reality.

#2.  We Believe Success Must be More

Billions.  It seems that’s the new fantasy base.  Millions isn’t enough anymore.

We build.  We grow.  We strive for the next level.  We want the jackpot.  The whole thing.  The big payoff.  All of it.   Freedom.  Complete autonomy.  Everything we could want or have.

More.  It has to be more.  This isn’t enough.

What We Need to Understand is Enough is Pretty Damn Nice

I ask small business owners that I coach how much they want to make from the sale of their business.   I love it when they answer $1 Million.  It makes the follow-up questions so easy.

  • Me: Why $1 Million?
  • Them: I don’t know, I’ve just always had that number in my head.
  • Me: OK.  What does life look like with a $1 Million sale?  What do you actually do?
  • Them:  Hmmm . . . I’d like to . . .Well . . .I guess I’d take some time off, and then . . .
  • Me:  O.K., we’ll explore that more, but how does life look different with a $950,000 sale?
  • Them:  Ummm. . .

What life do you want to live?  What do you value?  Is your current business adventure leading you there?  Do you have a target for after you sell (or even for right now), or is the target simply “more”?

If a $500,000 exit provides you access to the life you want, is it worth 7 years to create a $1.2 Million exit?  Maybe, but maybe not.

Am I missing out?  Perhaps I don’t really understand how much better life is with private jets and “billions”.  That could be, but my “enough” didn’t need that.

When I tell my story of exiting my first business, I tell people this truth of my own journey: I didn’t make “never work again” money, but I made “never work at a job I don’t want to” money.   Call it “screw-you” money.

For me, it turns out, that was enough.  And enough is pretty damn good.

If you really want more, that’s fine.  But if you think you want more because you haven’t asked what enough is . . . you’ve cursed yourself to constant pursuit of more, and I don’t see how that can ever be enough.

#3.  We Believe This is Who I Am

I am a small business owner . . .no, that leaves too much wiggle room.

I am the owner of ABC, Co.

There.  That’s who I am.  I’ve been that for 7, or 12, or 29 years.  That’s defined me professionally, and personally.  This is who I am.

If I sell my business, who I am will be lost.  I will no longer be me, as I will no longer be the owner of “ABC, Co.”.

What We Need to Understand is You Are, and Will Continue to Be You (and Maybe Better)

I’ve written in the past about my deep love for the “end of the story” and the new beginnings that it allows.  The doors that are opened and the new possibilities to be explored are scary, exciting, and overwhelmingly amazing.  Like most, I was terrified of the idea of selling my business at first, but after three successful sales I have come to love that time period.

You can too.

Yes, you were the owner of ABC, CO.  But after you sell the business you get to take everything you learned, the network you built, and the proceeds of the sale and become - - - whatever you choose to be.


Buy another business.

Start-up founder.

Real estate investor.


You will continue to be you, but without the baggage that came from being the owner of ABC, Co.

Of course, it can be hard to realign yourself after a transition this large.  I know it was for me the first time.  But as I walked the path, I developed a deep love for the freedom the decision to sell provided.   Ironically, each time I’ve gained that freedom, I’ve used it to commit anew and start the journey over with another business.  But that search and recommitment has been more invigorating than I knew possible.

I don’t know, and can’t credit the source (it’s not me) but I always loved the phrase shared with me early on in my career:

If you are what you do, what are you when you don’t?

Loss of identity is a real thing for owners who sell, and the terror of it can be a huge barrier to considering a sale.  But like everything you’ve taken on as a business owner, this is something you can tackle if you put your mind to it.   The possibilities that can be created by doing so are amazing.  You will come out the other side the same, and different.  Better in ways that are hard to imagine from the front side of the sales process.

Let Go of the Shame

Considering the sale of your business is terrifying, and we often respond by hiding in words like “never quit”.  Especially the first time through.  The possibilities it creates in our head are simultaneously fuzzy, warm and uncomfortable.  Shame mixes with profound wonder at the idea of being able to start-over.

Don’t let the complex emotions inspired by the concept of selling your business keep you from exploring what might be the best move you could ever make for your career, your business and your life.


Have you asked: Will I be able to sell my business?

Mike Finger

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