“I Wish… I Wish…” – The Words No One Should Have to Say

Individual contributors, mid-level leaders, senior executive leaders and entrepreneurs:

Do you have any regrets in life, in career, or in business?

There are two words I hope none of us ever have to say at the end of our lives. Two words that carry the weight of missed moments, lost opportunities, and silent regrets: “I wish… I wish…”

At my recent dentist visit, something unexpected happened that reframed how I think about legacy, purpose, and the roles we embody every single day.

A Lesson from the Dentist’s Chair

I was sitting in the dentist’s chair when I learned the owner, who’s now in his 70s, was selling his practice after 42 years of service. I curiously asked him the one question many people avoid until it’s too late: “Do you have any regrets?”

He paused for a while and in that moment, I saw him think for about 70 years in silent reflection and then said quietly,

“I wished I visited my parents more. They were only a few hours away. I should have done more.”

Those words hit me so deeply that the pain in my tooth disappeared. Again, I asked gently, “Are they still alive?” He looked down to hide the cloud forming in his eyes and whispered: “No. They’re not.”

Today, he’s selling his business so he can spend more time with his grandson. Every Tuesday he brings him toys. His daughter “complains about frequency of toys but in a good way. To me, the dentist found a way to leverage the power of regret. Those Tuesdays are his way of building a legacy with the time left ahead of him. The dentist’s story taught me something profound:

Regret is the price we pay for the legacy we neglect.

At the end of the day, most people don’t regret the goals they didn’t hit. They regret:

• The relationships they didn’t nurture
• The moments they didn’t show up for
• The courage they didn’t exercise
• The roles they neglected
• The potential they left untouched

Because true legacy is the effort behind your goals and the greatness you bring into your roles. Legacy isn’t something we think about at the end of life. It’s something we practice intentionally, deliberately and consistently in the chances we get every single day. This realization shaped one of the most important tools in my Executive Coaching Framework: The Roles & Goals Legacy Grid. It helps you evaluate six core roles of your life and asks you to reflect on four vital questions:

1. In which roles do I want my presence to really matter?
2. If someone told the story of this role 20 years from now, what would I want them to say?
3. What consistent actions will make my legacy sustainable?
4. If I left today, what would keep moving because of the impact I created long ago?

This is how business professionals intentionally build legacy that will last for generations to come.

A Challenge for You

Strive for excellence in every role of your life.

Choose your legacy today before your career and life whisper:

• “I wish someone saw me.”
• “I wish I spoke up.”
• “I wish I believed in myself sooner.”
• “I wish I showed up.”
• “I wish I had more time.”
• “I wish I hadn’t waited so long…”

Remember, your choices, your actions, your presence, your purpose are what build your legacy every single day.

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Felix Okoth, PMP®

Executive Leadership Coach | Global Engineering Leader | Keynote Speaker | Author | Podcast Host

Helping purpose-driven professionals go From Invisible to Influential

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