How Do You Avoid a Lifetime of Regrets?


Some questions in life are easy to answer and barely require a second thought. “Do you want fries with that?” “How would you like your steak cooked?” “Can I get you another beer?” 

Other questions are hard—so difficult in fact we avoid them altogether. Oh, we might give them brief consideration or lip service, but we rarely go beneath the surface.

I faced such a question many years ago sitting in an airport for another redeye flight home. The inquiry came unexpectedly from an individual I barely knew at the time.

“Who are you?”

Like many people do, I began to answer with typical responses. I gave my name, job title, marital status. The standard stuff. But I knew that wasn’t what he was asking.

Ironically, the question he asked came at a time when I was writing a book to help people understand their true identity. And honestly, the lack of surety and substance in my reply that night concerned me.

For months, that seemingly simple question kicked my ass and kept me awake. If I couldn’t offer a real answer for myself, how in the world could I possibly guide others through their own discovery process of identity?

Nonetheless, I finished writing my book on the subject. And while it had some solid content and sold thousands of copies, I’m afraid it probably failed to go deep enough and get to the heart of the matter for my readers.

While I continued to forge ahead in my career, I never forgot that haunting question, “Who are you?” Sadly, the fallback answer I typically told myself 99% of the time always included the standard stuff.

Today, the shortened version of my bio reads, “I’m a husband, father, writer, speaker, coffee snob, pipe smoker, bourbon drinker, and person of faith. I’m also friendly disrupter of the status quo on a mission to end aloneness and help people live with authenticity.”

Better. But still incomplete.

It sells on social media but says nothing really.

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Identity or Conformity

In the last few months as I’ve transitioned to a different career path, I’ve made a statement that has caused a few people some discomfort.

“After 30 years, I’m sure I became a pastor because it was the path of least resistance.” 

I’m not alone. And neither are you. Most people tend to follow the path of least resistance in life and take the easy way out when possible. We conform to bring others comfort. And we bury the best of ourselves to buy the acceptance of others.

For much of my life, I’ve traveled the path of least resistance. When the road got rough, I resigned to the pressures instead of focusing, following through, and finishing1. And honestly, I admit that propensity still plagues me.

Last week, I was chatting with a Facebook follower about my last blog, Are We Addicted to Inauthenticity. In our friendly text exchange on Messenger, he asserted his belief that being authentic is impossible.

What he wrote next is what I haven’t been able to shake, “I gave up trying at age 14.” For him, the path of least resistance was to give up and give in to the pressures he faced as a teen. The poor fellow folded before he turned fifteen—and it has followed since.

My friends, that’s the bullshit we’ve bought into that hurts my heart and powers my passion. While I haven’t completely figured out the answer and antidote—yetI do know the path to wholeness and authenticity begins by knowing yourself.

Knowing yourself means being in the world—not of it. Knowing yourself means being the light of the world—not hiding your light under a bucket. It means placing a greater value on the peace of your inner world rather than on the pressures of your outer world. Realistically, it’s what Robert Frost calls, “The Road Less Taken.”

Knowing yourself is a subversive act that solicits more hard questions we must consider.

Does our world celebrate the status quo? Have we sacrificed identity for conformity? Have we abandoned authenticity for safety and sanity? If we answer to any of those is yes, we must answer one more hard question. Has it been worth the cost we’ve paid?

The path of least resistance leads to a lifetime of regrets.

Take the next exit. The rocky road awaits.


As always, I’d love to hear you thoughts. Please comment below or email me.

• • •


I encourage you to carve out some time and consider the exercise below. Answer the “Who are you?” question without using any of the following:

  • Name

  • Job Title

  • Profession

  • Relationship Status

  • Culture

  • Faith

  • Things You Did

When you remove restrictive labels, you discover your real identity.

Who are you? What do you want to do? How do you want to do it? Those questions require serious consideration. Regardless of your age or position in life, CompleMentor can improve your life and leadership. Please contact them today.

If you need help with the subject matter of this blog for your personal or professional life, email me to discuss one-on-one consulting options. I will reply personally. —T.

Timothy Eldred is a writer, speaker, and friendly disruptor of the status quo with a mission to end aloneness. He gives leadership and provides strategic support to profit and not-for-profit organizations to develop a sustainable culture of authenticity.


My friend and CompleMentor, Monty Hipp, is constantly reminding me of this matter.