CHU On Self Leadership – Baby Boomers: Stop Using the C-Word! 

Summary/ Net: Boomers, please stop believing that you “can’t do” things you never mastered before – or better yet – tried without success in the past.  Use “The 5 T’s” to overcome your lack of confidence: Try, Training, The Right Tools, The Requisite Time, and Trial and Error.

I wrote this for three reasons:

  1. Few things frustrate me more than hearing friends, family members, and colleagues say they “can’t” do something when I know they have the capability to learn how to do it.
  2. I recently realized that over the course of my adult life, I have – on multiple occasions – told myself that I “can’t” (or more correctly, “couldn’t,” as these were in the past) do things I later learned to master. A few examples:
  • I thought I couldn’t learn to use a computer, then use Excel, then use “v-lookup” and “pivot tables.” Now, I have completed advanced Excel courses, can create PowerPoint faster than I can talk, and am learning Python.  Similarly, I went from not knowing how to create a simple video to making videos for my nonprofit, policy/ political, and other clients, learning Adobe Premier Pro to do so.
  • I thought I wasn’t handy; couldn’t be trusted to hang a shelf in our apartment. Today, I know I can do finished carpentry, recently building a cabinet that looks like a speaker with a lift to conceal a 70-inch TV in my living room.  I also made a set of bookcases that match the ones built by my friend and excellent carpenter/ contractor “Mr. Wayne.”
  • Although anyone who knows me today has a hard time believing this, not that long ago I thought I couldn’t ride a “drop bar” road bike. So much so that when I started cycling again about 12 years ago, my first purchase was a “flat bar” road bike.  Now, I ride several thousand miles a year on my beloved PARLEE RZ7 – training for endurance cycling events to raise money for research to find a cure for pediatric brain cancer.
  1. I also realized that – living in the 21st century – there are 5 “T’s” we can all use to overcome this lack of self-confidence in our ability to learn how to do most anything: Try, Training, The Right Tools, The Requisite Time, and Trial and Error.

The “5 T’s”

  1. Try

You never know what you can do until you try

– C.S. Lewis

Just try new things. Don’t be afraid. Step out of your comfort zones and soar, all right?”

– Michelle Obama




It’s a trite tautology to say that we fail at 100% of the things we never attempt, but it’s also true.  That said, we have the benefit of living in the 21st century and the “4 T’s” dramatically increase the odds that we can all master new skills and capabilities if we summon the courage to try and take advantage of the resources to help.

  1. Training

Training is everything.”

– Mark Twain

“Anyone who stops learning is old, whether at twenty or eighty. Anyone who keeps learning stays young.”                                                                                 –  Henry Ford

While “I don’t know how to do X” or “I’ve never been trained how to do Y” prior to 2008 might have been somewhat acceptable excuses for using the C-Word, that all changed in 2005, when YouTube was created.  Today, YouTube has over 90,000 lectures, tutorials, and courses on a wide range of subjects.  Want to learn how to build a finished carpenter-quality bookcase? Check!  Or to play almost any song on any instrument? Check! Adobe Premiere Pro? Check!

I remember first realizing this when my son Myles started his business making custom grip tape for skateboards in 2011 at age 12.  He sat at our family PC in the kitchen and taught himself how to use Photoshop to turn photos into drawings and then separate the images into individual layers to make stencils for spray painting the color images on the grip tape.  I remember asking Myles why he was using YouTube to learn Photoshop when his skateboarding coach’s wife was the lead instructor at New England School of Digital Photography.  His response – “I can do it myself.  And this is faster.”

In addition to YouTube, there are hundreds of online courses available from excellent providers, including Udemy, Kahn Academy, and LinkedIn Learning.  And most major universities are making their classes available to audit online for free.

  1. Tools

“Make sure that you always have the right tools for the job. It’s no use trying to eat a steak with a teaspoon and a straw.” – Anthony T. Hincks

“Technology is nothing. What’s important is that you have faith in people, that they’re basically good and smart, and if you give them tools, they’ll do wonderful things with them.” – Steve Jobs

Again, living and learning in the 21st century we have so many excellent tools available to help us learn and do new things.  Using Apple device apps like “Clips” which automatically convert voice to text captions on videos or the right “jig” to make sure the holes for shelf clips on a bookcase line up perfectly makes these formerly formidable tasks incredibly easy.

My transition from telling myself I couldn’t be trusted to mount a TV on the wall to hanging French doors and creating matching built in bookcases in my office was forced on me by the Covid-19 labor shortage.  My awesome contractor extraordinaire “Mr. Wayne” was too busy with larger renovation jobs to help me with my “house perfect list” projects, so I decided to figure out how to complete them myself.  I soon realized that I could buy both the materials – and some really cool “man toy” power tools like a power compound MITRE box – for less than paying someone else to do it for me.  And I get the wonderful byproduct of having more cordless power tools than I ever dreamed of.  (A colleague once said to me: “You realize you are a little boy in a grown man’s body!)

  1. Time

“Time isn’t the main thing, it’s the only thing.”                                                                                                        – Miles Davis

“Amateurs sit and wait for inspiration.  The rest of us just get up and do the work.”                             – Stephen King


To learn new things, once you have acquired the requisite training and tools (and training on how to use the tools), you have to put in the time.

Depending on the complexity of the material, skills, or project you are committed to tackling, the requisite time will vary.  As someone who has worked my entire adult life to manage the challenges of ADHD, I often find “getting started” to be one of the greatest hurdles to learning new skills (or completing tasks).  I have found that setting my iPhone timer for 15-20 minutes a very helpful strategy for getting going, saying to myself “Anyone can do this for 20 minutes!” And I often find myself re-setting the 20-minute timer – at times for hours.

Depending on the complexity of your challenge, great strides can be made over a few weeks or months by learning and practicing for as little as ten minutes a day.  I am a great fan of the book Atomic Habits, which praises the compounding power of just doing something one percent more each day. Language learning apps like Babble and brain training tools like Brain HQ are great tools for learning new skills and improving focus, short term processing memory and pattern recognition in bite sized lessons and games that yield significant improvement with little time invested on a daily basis.

Atomic Habits also recommends developing “habit stacking” routines, where you combine new routines with existing ones.  Examples from the fitness world include doing 50 air squats and heel raises while taking your daily shower or completing a few language and brain training exercises from Babble and Brain HQ while on the treadmill or stationary bike.

Other types of intellectual capital can be created by investing in a few hours of training.  Examples include specific software skill hands-on training – a few years ago, I invested in a one day 6-hour advanced Excel course produced by the company ONLC and was amazed at how much I learned (and was able to focus thanks to the extraordinary instructor and course design) and was able to apply immediately after completing the course.  A one-or two-hour cooking class can transfer a ton of skills and knowledge toward mastering new recipes and techniques, and weekend tennis or golf schools can raise your game to the next level.

  1. Trial & Error/ Try Again.

“Our greatest weakness lies in giving up.  The most certain way to succeed is always to try just one more time.”                                                                                                                                                                             – Thomas Edison

“A person who never made a mistake never tried anything new.”                                                                                                                                                           – Abert Einstein

The journey of learning new skills will often require a healthy dose of “trial and error.”  I learned the hard way during my “self-apprenticeship” to acquire finish carpentry skills to practice any permanent tasks – e.g. cutting, drilling and especially routing – on scrap wood before trying to rout out the space to countersink hinges on a finished door!  “Measure twice, cut once” is also a helpful mantra.

While writing this article, I thought a lot about why I succumbed to the negative self-talk of the “C-Word” for so many years.  One of the root causes of this destructive thinking appeared to be pervious failures at specific tasks, which given my career success as both an entrepreneur and consultant, is puzzling.  Although consultants and entrepreneurs/ business leaders have very different skills and attitudes on many levels, one phase both professions abhor is “We tried that already, and it didn’t work,” a phrase often used by “experienced” clients, managers, and traditional investors to kill innovative ideas, approaches, and products.


Imagine if Thomas Edison had held that point of view – I might be writing this article by the light of a whale oil lamp! Edison “failed” more than 1,000 times before producing a working light bulb, but is remembered for his beautiful quote “I have not failed 10,000 times–I’ve successfully found 10,000 ways it will not work.”

Or if Apple had concluded that a personal assistant/ communication device could not be developed and commercially successful based on the failed Newton – a brick size device launched in 1993.

While I am a huge fan of the trial-and-error method and learning from one’s mistakes, I also keep in mind Einstein’s definition of insanity as “Doing the same thing over and over again but expecting different results.”  To stop using the dreaded “C-Word” and happily live on a vertical learning curve, it’s important to differentiate between learning new skills or creating new products and services that require constant repetition with many errors along the way – such as learning to play Hendrix’ Little Wing on guitar – with those that require continuous innovation and improvement – like the “Newton to iPhone” example above.  One of the greatest lessons I learned from my late father was the power of “Creative Persistence,” and I have often said that creative persistence is the key to all entrepreneurial success.  (For more on this, see my article “A Tribute To the Original Collaboration Evangelist.”)

Will Koehrsen’s excellent article “The Mundanity of Excellence: Talent Does Not Determine Success and Why That Terrifies People,” echoes many of these points in his excellent summary of “The Mundanity of Excellence” by Daniel Chambliss and also draws on insights from the books Peak: Secrets from the New Science of Expertise (Ericsson); Endure: Mind, Body, and the Curiously Elastic Limits of Human Performance (Hutchinson); Grit: The Power of Passion and Perseverance (Duckworth); Principles (Dalio) and The Power of Habit (Duhigg). Koehersen’s summary of these great works:

“When we objectively study excellence, we discover:

  1. Excellence requires doing small, ordinary things consistently right.
  2. Innate talent is not responsible for high achievement.
  3. Significant improvement results from qualitative changes in how you practice skills, not from doing more of the same.

I hope this challenge to those of my – and all – generations to stop using the “C-Word” by leveraging the “5 T’s” is of value to you.  I would appreciate both your feedback on this article and any strategies you have used to learn and master new things.