Breaking The Habit Of Quitting

I enjoyed many hiking and backpacking trips throughout my teens and early adult years. I loved to challenge myself. In my late 20s and early 30s, I slayed many mountain peaks and continuously sought new adventures. Skydiving, bungee jumping, countless 5k mud runs, you name it, I was game. There was no quit in me.

This “never quit” attitude followed me in business. Sure, I would pivot when I thought it most advantageous, but I did not quit. With each new venture, I became more and more successful.

Skydiving over Lake Elsinore
Skydiving over Lake Elsinore

Enter my mid to late 30s. I had a business startup that never took off. I’m not here to play the “blame game.” I lost about $25K. I’ll add that I also lost a year of my life in its development, but that was not a loss because I learned so much.

Still, I wouldn’t consider this a “quit.” I was pivoting to something better, and I’m so glad I folded that hand when I did.

There was a point where I realized not to throw good money after bad money and that business was bad money. Partners that didn’t perform, a product that wasn’t being completed, and a salesperson that couldn’t sell. I was done. I saw what was unfolding and made the moves necessary to escape the impending financial fallout. I was lucky to get out with only losing $25,000. Hell, it may have been more; I never kept track.

After some time away from the mountains, I returned to a favorite hiking challenge, San Gorgonio. The tallest peak in Southern California, with a peak of just above 11,500′. My preferred route is the Vivian Creek Trail. This time, I would tackle the hike in the snow. My first snow hike. I was fully prepared and ready to conquer the mountain. But I didn’t. Slow travel and some equipment failures meant that I would make it about 2/3 of the way before having to turn back.

The next year I set out for a second attempt. This time, instead of trying to make the hike in a single day, I brought adequate supplies for an overnight trip. I had the mountain to myself. In a word, my surroundings were “majestic.”

Unfortunately, the second trip ended early again. More equipment failures, freezing temperatures without waterproof gloves, and a mountain lion all played games with my head, and I chose to turn back, unsuccessful in my attempt. People tell me that I made the right decision, and agree with them openly. Privately, in my head, I know that, in hindsight, I quit. I could have pushed myself into and through the night. I could have warmed myself up. I didn’t. That was a choice that I made.

I chose to quit.

Standing at the base of San Gorgonio Mt. before my first summit attempt in winter.

A year or two later, I decided to take on my next challenge. I was an avid mud runner and decided to take on a Spartan 10k. I had finished numerous 5k obstacle runs with no issues and wanted to push myself. Unfortunately, what was assumed to be a partial shoulder tear and a heel spur in my right foot, which triggered plantar fasciitis pain, would be an additional challenge that I would face.

Now, I know there was no way to accomplish the obstacles with the shoulder injury. My limited range of motion and the lack of shoulder strength meant that my best would be to finish just the run part of the race. With the plantar fasciitis issues, I would go as far as I could.

At just over the 5k mark, I decided that enough was enough, and I pulled myself from the race. Again, I quit. Again, people said that it was probably for the best. Again, I agreed with them. And again, I know that, in hindsight, I could have done better.

The Quitting Attitude

That first quit when heading up San Gorgonio was the first time I listened to the self-talk that questioned what I was doing and allowed my lower self to persuade me to throw in the towel. After giving in, it became easier the second time and the third time. Looking back, I could have pushed myself. I could have accomplished all of those trips and goals. Yes, I had valid excuses. In the end, that is precisely what they were – excuses.

Over the last month of soul searching, I realized that I’d broken a stronghold in me that once allowed me to push myself past my limits. I opened myself up and allowed myself to create a quitting attitude.

Once I recognized it, I got angry with myself. How could I allow myself to go down this road?

Well, it ends now.

One thing that I want to be sure of is that allowing myself to quit does not spill over into my professional life. That’s not something I am willing to let myself do. So, it’s time to change course.

Changing Course: My Plan

The most powerful part is recognizing that I am heading down this negative path. Doing so and having an inner no-bs conversation set me up to right my own ship. Now, it’s time to undo the prior quits and get me on the right track.

I must face San Gorgonio again as a snow hike and reach the summit. I must rerun the Spartan race that I tapped out on and finish.

Last, I must continue challenging myself and fighting my lower self from casting seeds of doubt. This last step must be ongoing. Doing so will retrain my mind to break the cycle of quitting.

This means uncovering things that I think I’m not good at, setting a goal for whatever that is, and accomplishing that goal.

The only cure is to live the cliche of “get comfortable being uncomfortable.”

Creating A Plan

The old adage, “if we fail to plan, we plan to fail,” seems fitting. In retrospect, complacency is what led to a lack of planning. I was used to achieving my goals. Over time, my preparation became nearly nonexistent. This lack of planning contributed to the failures. It created an atmosphere that allowed for self-doubt to fester.

So, the next step after recognizing the negative pattern is to create a plan for up-and-coming challenges.


A plan is great, but sticking to that plan will require help. I am a strong proponent of accountability. My business partner and I check in almost every weekday morning and keep each other accountable for our deliverables. In our business networking groups, the totality of the chapter membership keeps each other member accountable through weekly reporting. Also, I am accountable to myself.

At every step and action, I must be purposeful in ensuring that I am moving toward fulfilling my goals. When I set out to accomplish a physical challenge, I must keep myself accountable for the steps and milestones in my plan.

Also, for each of the milestones, I will need to have a small support group that I ask to keep me accountable and check in with me weekly or monthly.

This accountability is not meant to transfer a normalized friendly relationship into a parent/child or a dominant/subservient relationship. Also, accountability should not focus on an internal punishment system where only feedback occurs when tasks go uncompleted.

Therefore, selecting the appropriate people in my life to keep me accountable is crucial.

A Hopeful Future

Quitting an attempted summit push or a silly mud run is insignificant to my life and carries the same value for most people. It’s a nothingburger.

But for me, it is a small red flag that should be addressed. It is an action that I do not want to make a habit of. Therefore, I will act and make the necessary changes to avoid creating a negative habit.

By creating a plan of action and leaning into my share of influence to keep me accountable, a simple process for success can be created, tested, and replicated in other areas of life that hold greater importance.