My Most Memorable Failure

I’m guessing there’s a very good chance that anyone who stumbles upon this post is a fan of the Tim Ferriss show. Just based on the numbers that’s a safe bet since Tim has more than 1.5 million followers on Twitter. I am a fan myself and, like many of you, I am responsible for more than a few of the 200+ million downloads of Tim’s podcasts.

His guests’ responses to his rapid fire questions always interest me so I’ve given some thought to what my own responses would be. Trouble is, with one exception, my answers are mostly boring.

Nonetheless, I believe in being prepared. So if Tim should ever ring me up and want to ask me some questions I’m ready. Here’s how I think the conversation might go down:

TF: What new belief, behaviors, or habits, adopted within the last 5 years, have most positively impacted your life?

Me: Meditation. I know, everyone says that, but it’s true. See, boring.

Tf: What purchases of less than $100 have most improved your life?

Me: I don’t buy a lot of stuff, so this is hard to answer. Groceries?

The fact that I had to think about this a lot and still don’t have a good answer tells you how boring my answers are.

If pressed I suppose I would say the Leatherman Wingman.

And I didn’t even buy it. Someone gave it to me as a gift several years ago.

I should probably buy another one though since the law of diminishing perfection states that once you find something you like it is destined to be discontinued.

TF: What books have you gifted the most to other people?

Me: In addition to not buying a lot of stuff I also don’t give a lot of gifts. I did once gift Confederacy of Dunces by John Kennedy Toole to my former stepfather thinking that maybe we could share a rare laugh together over a Pulitzer Prize-winning novel. Nope, but at least I tried.

TF: What would you put on a billboard?

Me: Maybe: “Index Funds” or possibly: “We only live in the present.”

TF: What do you do when you feel unfocused or overwhelmed?

Me: I usually make to-do lists and start doing the things that are most time-sensitive. Zzzzzzzzzzzzz

(At this point Tim is getting exasperated with my boring answers and is about to hang up, but he takes a breath and realizes he’s had a little too much Four Sigmatic Chaga Mushroom Coffee. He gives me one more chance.)

TF: How has a failure, or apparent failure, set you up for future success? Do you have a “favorite failure” of yours?

Me: How much time do we have?

TF: Look, I need to get something out of this call and so far, I don’t see it. So if you have something I can use take what time you need, but make it good.

Me: Ok, I do have a favorite failure. Allow me to set the scene. Here goes. . .

January 1990

Major historical events from January of 1990 include the Dow Jones Industrial Average hitting a new record high less than three years after Black Monday:

Dow hits new record high of 2810.15!!!!!

The Tower of Pisa being closed due to leaning too far:

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Good dog.


And me being a sophomore at the University of Florida:

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PE was still a college requirement back then and I decided I was going to take sailing. I had visited my aunt and uncle the previous November and they had taken me out on their J24 sailboat.

(The only reason I knew my visit had been in November was because we watched the Berlin Wall come down on TV – 11/9/89.)

So come the spring semester I registered for sailing class. I thought my prior experience with my uncle might give me a leg up since he’d taught me some of the terminology and he’d let me take the helm for a short stint. My stint at the helm would’ve been longer but during my tenure as skipper we narrowly missed ramming another boat. “Sorry dude!”

There would also be a bunch of knots to learn in sailing class and I thought I would be pretty good at that since I had been on the rope splicing relay team when I was in scouts.

Oh, and there would be a swim test.


I was not then and am not now a good swimmer. Ah well, I thought, I’ll just deal with that when we get to it.

Well we got to it pretty damn quick since the university wasn’t about to take the liability of putting any non-swimming students out on the lake. You passed the swim test or you didn’t take the class. Simple as that.

Oh, and the lake where we sailed was also filled with alligators. Florida has more than 30,000 lakes and they all have alligators.

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Dude, you can’t run faster than me let alone swim faster.

The Swim Test

The day of the swim test everyone in class met at a big outdoor pool. A few lanes were reserved for the test takers and the rest of the pool was open for recreational swimming. Yes, there was outdoor swimming in January.

I don’t remember exactly how many laps we had to swim but it didn’t matter because anything over two was beyond me. We also had to tread water for 5 minutes as part of the test. I’d never done that before and thought it might be my downfall. Turns out I didn’t even get to that part.

A couple of lifeguards were casually running the swim test. As one swimmer got to the half-way point of a lap the lifeguards would send the next person.

In addition to the 25 to 30 people taking the swim test there were probably another 30 or so college kids in the pool just messing around or hanging out. I thought it would be easy to blend in.

My turn came. I jumped in, started swimming, finished one lap and was completely exhausted.

Midway through my second lap my legs wouldn’t stay at the surface. They sunk. We were swimming in about five feet of water and the the next thing I knew my feet were on the bottom of the pool. I was no longer swimming.

Maybe No One Will Notice?

There were 50 to 60 kids in this pool and only two lifeguards. They couldn’t possibly be watching everyone at once. There was too much going on. There was splashing and movement throughout the pool. Just try to blend in I thought.

I told myself to just keep bouncing along the bottom and moving my arms like I was swimming and maybe no one would notice.

Do you think that worked?

A lifeguard on the other side of the pool started yelling something. “Ignore it” I told myself. I walked/swam my way to the wall and turned around to start “swalking” the other way.

The yelling got louder, now there were two lifeguards yelling and doing lots of gesticulating in my general direction.

Whoever it was the lifeguards were yelling and waving at hadn’t caught on, but he was about to.

Finally I couldn’t ignore them any longer. I looked at them from across the pool, pointed at myself, and mouthed an exaggerated, “me??” They responded with vigorous head nodding and pointing for me to get out of the pool.

I’d been given the hook, my performance had been gonged, my swim test was over and the result was in: FAIL.

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What Now?

Humiliated and embarrassed I dragged myself out of the pool and trudged off to my apartment to crawl under a rock and contemplate my alternatives.

The first thing that came to mind was the easy way out. There were tons of other PE options that didn’t require a swim test: Bowling, Golf, Badminton, Yoga. I could drop Sailing and add one of these other classes and be guaranteed of two things:

  1. Not having to take a swim test. (GOOD!)
  2. Not learning how to sail. (not good.)

I decided to sleep on it and see where I was on the decision in the morning.

The next day I had sailing class, but just a classroom session, we weren’t yet meeting out at the lake. At the end of class I approached the instructor and told her what had happened with the swim test.

She gave me two options. I could drop the class, or I could meet her at the indoor pool the next day and she would work with me. In addition to teaching sailing she was also a swimming instructor.

I had serious doubts about whether or not trying the swim test again would be worthwhile. I had failed miserably. I hadn’t even done half of the required laps and hadn’t even started on the treading water part.

No matter how good the instructor might be she would still be working with some low-grade raw material. What could she possibly teach me in one session that would get me through the test?

I Guess I’ll Try Again

Nonetheless, I decided to showed up the next day at the appointed time and place.

To my utter and continued amazement the instructor worked with me for about 15 minutes and taught me how to swim well enough to pass the test. Not well, but well enough.

The secret she showed me was the survival backstroke. The test didn’t require a specific stroke and it wasn’t timed so I just did what she said and slowly but surely I completed the laps needed to pass.

Treading water for five minutes turned out to be fairly easy. When I got tired I simply floated up on to my back for a few seconds of rest. The first 30 seconds passed, then a minute, at a minute thirty I started thinking I might be able to do this.

Eventually five minutes had elapsed. I had passed the test. I would not be signing up for Bowling.

Night and Day

As I walked back to my apartment after passing the test the thoughts that went through my mind could not have been more different than the ones I had thought only three days before. The difference was literally like night and day.

In a matter of 72 hours I had gone from feeling humiliated, embarrassed, and resigned to my fate of not learning to sail, to discovering a new sense of agency over my own life. In that moment I realized I had much more control over the outcomes in my life than I had previously thought. As long as I didn’t shut down and accept failure I had options.

Even when repeated failure seemed like the most likely outcome, I allowed myself to be open to a different approach to solving a problem.

This was the first key lesson I learned from my failure:

If you want a different outcome than what you’re getting you have to be open to a different approach.

I’ve found that this lesson holds true in so many aspects of life. It doesn’t matter what you’re trying to accomplish, whether it’s building wealth, getting out of debt, reshaping your body, changing your career, or transforming your relationships. If you’re not happy with the current state of affairs you have to be willing to try something different even when there is no guarantee of success.

As Henry Ford notably said:

Failure is only the opportunity to more intelligently begin again.

I failed my initial swim test miserably. I could’ve left it at that and very nearly did. But instead I chose to be open to a different way of solving a problem. When I did this the once insurmountable hurdle was overcome.

So Did I Learn to Sail?

Yes I did. And as it turned out learning how to sail was a blast and really not that difficult. Funny how things never seem as hard as you thought they would be once you know how to do them.

Of course there was a lot fumbling around those first few days on the water, but I learned early on how to right a cap-sized boat. When your boat is upside down in sight of multiple alligators you figure out how to correct the situation very quickly.

An incident from our first day on the water left a big impression on me.  While most of us were just trying to keep our boats upright and our butts out of the water there was one kid who was zipping around all of us newbs. He was tacking left and right across the lake, weaving in and out of the rest of the mostly stationary boats. This kid had obviously done this many times before.

At one point he did something I had never seen. As his heavily heeling boat shot past me his body was hiked out to the point of being parallel with the surface of the water.

With total control he casually dipped his head backwards into a small wave and then triumphantly wrung the water from his hair with an easy flick of the head.

I had two thoughts:

  1. What a freaking show off.
  2. I am going to learn to do that.

By the end of the semester I had learned to do that. I got to the point where if I had enough wind I could hold the hiked out position, tilt my head backwards and watch the horizon race by upside down with my head only inches above the water. It was an exhilarating experience to say the least.

It’s also an experience that a few months prior I didn’t even know was possible. And therein lies the second key lesson I took from my earlier failure:

If you let the fear of failure make your decisions for you then you are denying yourself experiences and possibilities you’re not even aware of.

Wise old Mr. Ford had already figured this out and put it a bit more succinctly when he said:

One who fears failure limits his activities. 

And thus concludes the story of my most memorable failure. We’ve all had failures. What have you learned from yours? Did they involve alligators? Are you still applying the lessons learned?



  1. I tried to join a college choir that was very hard to get into. You had to audition against many others and as it turns out I’m not a good singer. But I signed up and to my dismay when we got to try outs it consisted of an unaccompanied (no music) solo in front of the hundreds of people trying out. I was bad and didn’t get in but it was a great lesson. A lesson in doing your best even when you see very little chance of success. I walked out of there knowing I wasn’t a singer which was fine but also knowing I could take rejection and even public embarrassment and not have it crush me. It was actually easier to jump outside of my comfort zone after that failure. Up to then I had been successful at most anything I had tried and I needed to understand the pain side of not winning better. That was decades ago and still stings as I type this, a little, but it was a lesson in counting the costs of failure in advance. There is no courage unless there is first fear.


    1. Steve – that sounds brutal and I can relate to your story in so many ways. There is a big difference between having a good voice and being a good singer. I play bluegrass music and have been in lots of bands. I’ve always been told I have a good voice but once I started doing some recording and playing with professional musicians I got humbled quickly. I struggled to stay on pitch when it was just me in the vocal booth (aka torture chamber) and everyone in the control room was just watching me and waiting for me to do it right.

      Facing rejection and public embarrassment and realizing afterwards that it’s not the end of the world is a very valuable lesson. A painful one, but nonetheless valuable.

      I hope your experience those many years ago hasn’t kept you from singing throughout life. Singing for fun with friends/family is a great activity. I’m convinced that it’s beneficial to your health.


      1. Agreed, I sang in a bunch of choirs after that, I’m not great but I can make a joyful noise and I know the basics. I also have done some acting and a whole bunch of public speaking. I just like performing.


        1. “Joyful noise” I love it, we need more of that in this world.

          I used to be so fearful of public speaking and avoided it at all costs. As a child I suffered through a lot of humiliation at the hands of my stepfather and an elementary school teacher. I always felt as if public speaking was opening me back up to that same humiliation so I never wanted to give it a try. But I always loved performing and the practice of being on stage with bands and music helped me get over the fear. And as it turns out I’m actually pretty good at it. Now I’ve even done some emcee work for big events at the office (~150 people). I’ve even wondered if maybe there’s a side hustle in there somewhere.


          1. There can be, I’ve done side hustling as a lobbyist and an expert witness, both of those are basically public speaking to a large degree.

  2. Failing is so important. I don’t do it enough because I don’t take enough risks.

    Your story is great. Glad you figured our the survival backstroke. That teacher really earned her pay with you that semester.


    1. Jason – I fear that I’m in the same boat as far as not taking enough risks. I listened to the Choose FI podcast today with Vincent Pugliese and it really got me thinking about needing to take more risks and not settling for just a “comfortable” life.

      Glad you liked the story. No kidding, that instructor went above and beyond with me.


  3. You had me cracking up with “swalking”.

    We listened to that Choose FI Episode. I think Mr. G is mentioning Vincent in a post next week.

    Like Jason, I probably don’t take enough chances but sometimes I know my limits. Good for you that you pressed on. Sometimes “good enough” is all that’s needed.

    Four Cigmatic, tango dancing, me undies, “teasing out” the lessons. Tim is out there.


  4. Hey Mrs. G!

    Yeah, I can swalk with the best of them.

    Learning that being good enough is sometimes all you need is an important lesson. I’ve been working on this with my son a lot and still don’t think I’m getting through. He is such a perfectionist (don’t know where he gets it from) that he won’t try things unless he’s convinced he can master them first time around.

    He’s facing his own swim test demon now with scouts. Like father, like son. If he can just get through the swim test everything else will be a piece of cake. But all he can see now is this giant swim test monster in front of him.

    I’m enjoying following your progress on the road to Groovy Ranch.


  5. I love that you answered Tim’s questions from Tribe of Mentors. I may have to steal this idea.

    Failure is the best way to learn pretty much anything. It stings at first, though that sting is what makes the learning experience so great.


  6. Yeah, do it. He has even more questions that I didn’t use.

    I agree that there is so much to be learned from failure if only we can allow ourselves to accept it, absorb the lessons and move on.

    It does seem like the stakes of failure get higher the older we get, which makes me more resistant to take on new risks. But maybe the stakes were just as high – relatively speaking – when we were younger and we just learned to get over it and take some chances?

    Thanks for the comment. Not sure why all these comments are dated January 31. Probably due to my WordPress failings.


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