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.





Near the end of Duke’s Sweet 16 victory over Texas Tech, Coach K (Mike Krzyzewski), one of the winningest coaches in college basketball history listened to his players – who asked him to let them change from zone defense to play “man to man.”  He agreed and Duke went on to win and, after beating Arkansas and will play in tonight’s Final Four matchup vs. North Carolina.

Think about that for a moment – Coach K has been coaching college ball for 48 years – that’s more than five times the combined college basketball experience of his starting five players.  By listening to his players and changing his mind, he exhibited an extraordinary level of confidence in himself and his young team.

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Leveraging Your Greatest Sales & Marketing Assets – Intellectual Leadership

Net: CEO’s and other company leaders with a enterprise view of their operations are uniquely positioned to identify and share best practices in all areas.  This opportunity can be greatest in organizations that operate in multiple locations with a lot of entrepreneurial flexibility to pilot new ideas, especially in sales and marketing. One way to capture best practices if to identify your brand’s most compelling assets and challenge yourself and other leaders to make sure you are utilizing both your most powerful messages and the most effective 21st Century communications media for sharing them.

My education as a consumer marketer wasn’t always pretty.  Among other screw-ups (see Leading by F***ing Up), our launch marketing campaign for AIR MILES Canada was so bad it was featured in a popular case study taught at the University of Western Ontario’s Ivy School of Business.  But somehow we managed to correct, learn from and survive from our mistakes and went on to enroll over 70% of Canadian Households as active members in the program and the company (now the LoyaltyOne Division of Alliance Data NYSE ADS) continues to win awards as one of the most recognized and respected brands in the country.

One of the insights we had in our earliest days was to make sure we identified and leveraged every potential sales and marketing asset available to us.  That included assets like the phenomenal support of our partners like Canada Safeway, Shell and Bank of Montreal/ MasterCard and the opportunity to co-brand our start-up with these extraordinary franchises.  We also created opportunities for partners to share their co-branded marketing, data-based direct mail, email and social media marketing and the business results from these initiatives at quarterly MAB (Marketing Advisory Board) meetings.

Recently, I had the opportunity to attend several inspirational Year Up Graduations, from Miami to Atlanta to NYC.  In addition to hearing the incredible stories of transformation told by the young adults we serve, I also noticed a number of “best practices” being implemented by our regional teams across the country. On the flight back to Boston, I took a few minutes to reflect on the most powerful assets available to all of us who work at Year Up that can be leveraged to communicate our value proposition to the organization’s stakeholders, including our corporate partners and potential targets, our investors, future employees and students.  Realizing that I have not always been the most thoughtful and strategic about leveraging these assets, I sketched out a small matrix to use as a kind of “check list” for our work:

The matrix forces us to think about the potential assets available to us when preparing for stakeholder engagement – Year Up Student Success Stories; the Value our Corporate Partners tell us they receive from working with Year Up; our incredible growth of the number of students we have served (from 22 to 4,000) and the corporate partners who have hired them (from 12 to 250+); and the endorsements of third parties, including leading industry groups, foundations, investors, academic institutions and others.  It also reminds us to use the most effective 21st Century communications media to share these assets.

We originally used this when developing a strategy to grow our partnership with individual companies, but more recently are also using it as we think about maximizing opportunities within industry verticals like finance, insurance, health care, technology and education.

If you are interested in learning more about Year Up’s assets and media/ communication opportunities, a few details follow:

  1. The voice and transformational stories of the young adults we serve.

Ideally, we would all be able to take at least one student with us to every Year Up stakeholder meeting, or better yet, to get every stakeholder or influencer to spend some time at one of our amazing sites with a few students.  But we don’t live in an ideal world and can’t always do that.

The good news is that we have several options for virtually bringing our students to stakeholder engagements, including the incredible student success stories produced by our marketing group, student pictures and quotes like the ones in our presentations and our screen savers and many incredibly powerful videos, including the 60 Minutes episode; our Cyber Security video that features CISO’s from leading companies like LinkedIn, Symantec and Salesforce and several students and the JP Morgan Chase video staring several AML and other alumni working at Chase and (then CIO) John Galante.  Our marketing team also recently developed a 90 second video “mashup” that combines clips from the GE Year Up Partnership video with those from Angel Navarez’ graduation speech.  It is one of the most powerful and efficient ways we know to explain what we mean by “Crossing the Opportunity Divide.”

  1. Year Up’s growth and track record of success

Although we are all used to seeing this chart, business leaders and other stakeholders often have the following reaction: “Wait, it looks like you continued to grow right through two recessions” – something most companies were not been able to do.

The leading nonprofit strategy consulting firm Bridgespan recently named Year Up as the largest, fastest growing and most successful youth serving organization founded this century.  That quote, when combined with a chart like the one below, almost always resonates with our corporate partners, business development prospects and other stakeholders:

  1. The world class brands and incredible support of and feedback from Year Up’s corporate partners

The privilege to use our corporate partners’ logos and – in many cases – literally co-brand Year Up with so many of the country’s largest and most respected companies and other leading enterprises is another incredible asset.

We have been able to do this since our earliest days and at times, it might be something we almost take for granted.  But those of us with entrepreneurial experience can assure you that most nonprofit and early stage for profit companies would die to be able to co-brand their enterprises with JP Morgan Chase, Salesforce, Harvard University, Facebook, Google, GE and so many others.

We recently added these charts showing the growth of two of our largest partners alongside the one above to demonstrate that Year Up has clearly been able to “serve our mission through the market:”

We also recently realized that we have been collecting Net Promoter Score (NPS) data as part of our Week 14 Internship Feedback Survey.  NPS is one measure of customer satisfaction that is used by many of our largest partners, including JP Morgan Chase, Facebook, AT&T and GE.  The NPS survey is deceptively simple, asking only one question: On a scale of 0 to 10, how likely would you be to recommend Year Up to a friend or colleague?  The NPS score is calculated by subtracting the percent of “0-6” responses from the percent of “9 and 10” ratings.

Average scores are published annually for many industries.  An NPS of 30 or higher is considered positive.  The average NPS Score from Year Up’s partner intern managers is 50 and ranges from 30 to 59.  The chart below compares recent Year Up NPS scores from several partners with the average NPS score of 14 for the U.S. staffing agency industry over the past seven years.

Another powerful way to share the success of our interns, graduates and alumni is through relevant quotes, like these from the 60 Minutes Episode about Year Up:

  1. Third party endorsers.

Many highly respected third party experts, leaders, publications and organizations have endorsed Year Up’s model and results, including The Bridgespan Group, 60 Minutes, Harvard Business School, American Banker and others.  Although not all of these endorsements will have the same impact with each stakeholders, over our 17 year history, we have received an impressive number of awards, business school case studies, and articles in respected publications and you can almost always find a relevant third party endorser that will resonate and add gravitas to Year Up for most stakeholder groups – corporate partner vertical, foundation, investor or community leaders.

One way to think about how effective you are at using these four assets is to refer to this matrix that lays out your assets and the media you can use to bring them to life in the most effective way possible:

We are not suggesting that you share or present multiple media sources of each asset in every stakeholder meeting.  We are suggesting that you use at least one media type (e.g. data driven charts, corporate partner testimonials) for each asset during your initial meetings to understand which asset and format hits both the “heart and head bulls eye” of those you are pitching to buy your products and services and/ or support your mission. Once you understand what message and medium is most effective to your specific stakeholder, you can then tailor future communications to emphasize those assets and media that area most effective with him or her.

We would love to hear your thoughts on creative ways you have used the assets of the enterprises you have led and the media you have used to showcase them.