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True Story: My Lawyer Told Me I was Crazy for Doing This! | Hollie Flynn

True Story: My Lawyer Told Me I was Crazy for Doing This!

My lawyer’s voice boomed, “I wouldn’t do this THING if my life depended on it!”

So of course, I did.  The very next day to be exact.

It was 1998. I was 26.  I took a business contract to an attorney for review.   I was trying to buy into a fitness franchise.  I was learning how to incorporate my first business. I was looking for rental space and negotiating a lease. I was setting up my first biz banking account.  I was being systematic, smart, and doing all the “right” things.  Having a lawyer review my contract was one of them.

I had dropped the contract off at the lawyer’s office and returned a couple of days later to hear his review.  I remember walking into his office feeling excited and proud of my big venture.  As I walked in, he dropped the 200+ page doc on the table, shaking his head as he said (very loudly as if he were in a courtroom instead of his quiet office),“I wouldn’t do this thing, if my life depended on it.” 

He explained the first 10 reasons why this was the worst business deal and contract he’d ever seen.  They made sense.  I could see where he was coming from.  But, the thing was…his life did not depend on this, mine did.  And to me, the risks were worth it.

I stood up, shook his hand, and thanked him for his advice. As I was walking out his door he said, “So, you’re not going to go through with this are you?” I hesitated (knowing often these things are best kept to myself).  I just smiled at him, and said, “Yeah, I think I probably will.”  He sighed.  And I left the next day to head to Texas (I lived in VA) to buy the franchise and begin training.

What I learned that day was that the great thing about someone saying “No way!” or “You are crazy!” is that it can firm up just how bad you want something. You need to know that. Sometimes you don’t know how badly you want something until it is taken away or you feel it might be. It’s good to know how “in” you are.  I don’t think I knew just how “in” I was until that moment with the lawyer.

Honestly, I’m all for seeking professional guidance and input.  I’m all for chatting with a few close friends or respected mentors.  Do bring in an expert if needed.   But the bottom line is, NO ONE knows more than you.  No one can measure how much heart you have. No one knows your passions or dreams and how they fit into your life better than you.

The experts, professionals, gurus, etc. are there to provide valuable insight and information. They are a part of the piece.  YOU are the bigger part.


Look at it all. Take what is helpful.  Leave the rest.

Popular + majority opinion = a status quo life.  If that fires you up, carry on.  But if not, then take in all you can.  Seek wisdom, not knowledge.  Trust yourself more than any other person on the planet. Follow your dreams.

That’s what you’re here for.

By the way, the buying into the franchise turned into being the best single decision of my life. It was a game changer that led to almost 14 years as a multi-club fitness center owner (I ended up buying 3 fitness centers), great income, and even greater personal growth.

It sparked my passion for entrepreneurship and gave me the confidence and know how to turn other passions into money making ventures.  It gave me the opportunity to design my entire life.

I believe with all my heart that NOT following your dreams is a far greater risk.  For me, what I feared most was reaching the end of my life with the question —What if?

Do you have a “What if?” — Something you really want to do. Something if you don’t try, you’ll always wonder?  Are you willing to take THAT risk?

Think about it.

Here’s to Dreaming Boldly, Trusting Deeply (in You!), and Going For It!


Hollie “no regrets” Flynn


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