A Few Simple Questions Can Show Us the Way

When I first met with my client, Denise, she was frustrated. With her business and her life. I wasn’t surprised – for many entrepreneurs, their lives and businesses are meshed together in a way where it is difficult to see the beginning of one and the ending of another.

But this day we had gathered for a CEO Strategy Day to unwind everything and get a plan that was exciting AND doable. Looking back, Denise was both an extraordinary and typical client. Extraordinary in that this was her third business she had started, she was amazingly talented, and well-known in the community and her industry. Typical in that she had come to me fairly discouraged that she said she no longer liked her business that much, her team frustrated her and approaching to what she thought might the next phase of her life and saw no opportunity for any kind of successful exit.

“It’s just too hard,” she said. “I don’t see how the business can ever run without me. As hard as I try, nothing seems to change with my team, and they just don’t get it.”

I listened for a bit and then we went to work and explored a slate of questions.

  • What was great about her business and her life?
  • What could be better?
  • Retirement loomed in her future. How would her days be different? What would be the same?
  • What kind of revenue could her business do?
  • What kind of income did she desire?
  • What did she like doing in her business?
  • What activities or tasks did she dread?

These were just a few of the questions we explored as we crafted her ideal life.

Once we had the answers, we then just worked backwards to determine what she would need to do to get there.

There were some interesting discoveries.

  • She felt trapped by her business and wanted to travel more.
  • She wanted to spend more time with her partner and her friends.
  • She wanted more time to create and more time to be physically active.

And yet, there were many things that she didn’t want to change.

  • She liked and cared for many members of her team.
  • She loved where she lived and enjoyed her philanthropy work.
  • She loved her clients and customers and enjoyed her business model.

And when we did a quick “back of the napkin” calculation, she realized that she already had enough assets and financial resources to live the life she wanted without selling her business nor ever working another day in her life.

Taking this inventory was life changing for Denise. By knowing that she no longer “needed to” work in her business, she soon “wanted to” work on her business. We spent the rest of our time together coming up with a plan to grow her team to support her business as well as putting guardrails in place for Denise to start living her life the way she had always wanted to when she started her business.

While I have some clients who are not as prepared, many of them come to a similar realization. Entrepreneurs, by definition, have something I call “the striving gene”! The striving gene means that we may stay stuck in the “wanting/planning/working on” mode.  This can play tricks on our minds and havoc in businesses and our lives because nothing ever seems right.

How do you fix this?

  • Be specific. Create real and tangible goals that you can measure with progress metrics and a dashboard that keeps track of your journey.
  • Review.  Look at your personal and business financial statements on regular, planned intervals.
  • Share. Make your targets and successes visible in your lives as well as our personal and professional support teams. Have as many visual cues as you need to not ignore your achievements.
  • Celebrate. Most entrepreneurs I know are already onto the next epic goal or adventure well before they’ve achieved their current goals. Our brains like completing tasks (i.e. that’s why it feels so great to cross something off our to do list.)

Consider these steps much like homing into your personal GPS. Once you know exactly where you are, it’s much easier to recalibrate and plan the next phase of your journey.

If you think a CEO Strategy Day would help you and your business, sign up here for a quick call with me to explore if it’s the right next best step.

One more thing…

This week I’m reading Jon Acuff’s new book – soundracks – The Surprising Solution to Overthinking. As a chronic overthinker (from a very young age), I’m loving this book. His style is light and humorous with a good bit of self-deprecation (he’s a sought-after public speaker.) Yet the material resonated deeply with me as he cited numerous examples and opportunities to change the soundtracks that influence our thinking and our actions (or inaction.) I typically prefer reading my books, but I couldn’t stop listening to the audio version (replacing all my podcasts this week.) Highly recommend this short but impactful book.