HOW DO I vs CAN I – the moment you knew you couldn’t give up on your business

I remember distinctly the moment I knew I couldn’t go back from being an entrepreneur. I’d sold my business after ten years of growing it. While I was ‘figuring out what’s next’ I decided to take a job. It sounded refreshing. I could do a good job, get a paycheck, have health insurance benefits, and let someone else make ALL the decisions and all I had to do was do a good job. A nice transition as I decided what to do next. Sounds nice, right?

Then I took a summer trip to Florida so my son and I could visit family. We rented a nice Airbnb on Treasure Island. My mom came, my niece and her family came from Virginia, all so we could spend some family time together. And I worked the entire time.  Huddled in a room the farthest away from everyone so it was quiet, while everyone went to the beach, had lunch together, and I missed every moment. I remember distinctly dragging my suitcase to the car to head to the airport and go home in tears. I’d never get these moments back.

Now, trust me, when I owned my last business, I worked through many vacations. It was not uncommon for me to be huddled over my laptop half of the time. But I had flexibility. I could take a break and go to the beach. I could get up really early and knock out the things I needed to then spend time with my family the rest of the day knowing my team had my back or would reach out if there were a true emergency. 

This time I was stuck on someone else’s schedule, chained to logging my required hours in the required time frame.

Crying my way down the stairs with my suitcase (the elevator was broken) I told myself – never again.  Never will I fly from Texas to Florida and not be able to spend time with my family and not have the flexibility to be present with them.

I resigned from that job. 

I shifted from “Can I start another business?” to “How do I start another business?”

Was it scary? Absolutely.
Frustrating? Many times.
But going back? Not an option.

Every entrepreneur has that moment — the one that breaks you open and forces you to decide. It’s not because you are making tons of money (often in these hit the wall moments you are in a cash flow crunch) it’s because the fear and frustration they feel when they hit the wall knocks away all the fluff and makes why they REALLY started their own business.  Not just for money – there are a lot of ways you can make money. It’s to:

• Be there when your daughter gets her award
• Sit beside your mother in hospice
• Know your work matters and your ideas are your own

In that moment, your mindset shifts from CAN I to HOW DO I — and that’s when everything changes.

Because “CAN I?” feeds fear.
But “HOW DO I?” fuels action

This week I had the privilege of being in a call where fellow entrepreneurs continue to say HOW CAN I to growing their law firms and growing them to support the life they want – the meaningful work, being at their daughter’s school award ceremony, and all the things. In the face of an uncertain economy, in the face of cash flow challenges, in the face of figuring out what’s not working and how to fix it. They say HOW DO I. Can I is off the table.

So tell me — what’s your WHY for being an entrepreneur?
And what was the moment you knew you could never go back?