Tag Archives: purpose

On Turning a Life Around. And Companies.

I had lunch last week with a guy named Kenyatta Leal. I met Kenyatta through the Last Mile program, which teaches incarcerated men to code software and, in the process, prepare them for “reentry” with skills, confidence, purpose and community.

Kenyatta was one of the first prisoners to go through the program at San Quentin. After a difficult childhood, he got into drugs and committed a crime for which he was sentenced to life in prison.

Kenyatta is now released, working for a Silicon Valley company, and is one of the most purpose-driven people I have met, especially when it comes to helping other prisoners.

Our sandwiches went untouched as we got lost in the conversation about turnarounds: what makes someone decide to turn their life around?

For Kenyatta, it wasn’t one big epiphany, but a collection of experiences that added up to a change in mindset, including…

  • Listening to counselors who urged him to take responsibility for his actions instead of blaming others;
  • Receiving the “tough love” letter from his mother while he was in solitary confinement telling him that if he wanted to get out, to start acting like it and stop complaining;
  • Realizing his Grandmother’s adage that we’re a composite of our five closest connections; thus prompting him to end his relationship with toxic friends;
  • Agreeing to become a founding member of the Last Mile program;
  • Sharing his experiences with others on a similar path.

Nothing hits the gut more than stories of turnaround, from Les Miserables to It’s a Wonderful Life to Robert Downey Jr. And that whole Jesus “rebirth” story seems to be pretty popular.

I believe it’s core to our programming as a species, not just the domain of self-obsessed Americans. We all benefit when members of the tribe are healthy and contributing. We find joy in the joy of others. So we celebrate their return to health.

I’ve had a number of friends who dismantled their lives through drugs and alcohol – anesthetizing to relieve pain and loneliness.

But some of them managed to reestablish their lives. One guy literally dug himself out of a ditch to go get help.

Seeing people overcome addiction is a testament to what we’re capable of as human beings.

We all have egoic baggage that drives us to do dumb things – inner pain mixed with circumstance that drives isolation and poor decisions. Otherwise we wouldn’t have to worry about turnarounds.

Thankfully, righting the ship is possible. But certain elements must be in place:

  1. Family and friends who care about our long term fulfillment.
  2. Awareness of our destructive tendencies and the likely result of that path.
  3. Mentors and advisors who shed light on the enlightened journey.
  4. A reason why (we must take the harder road).

Watching you and your own turnaround over the last 14 months has been nothing short of amazing. It’s hard to put into words on a public blog, so I’ll do an interpretive puppet show later.

Needless to say, your work has inspired my own turnaround – from “can’t find my way” drifting back into purpose. And perhaps by fate, my purpose has come full circle into this very idea of the turnaround.

In my professional life, I started working with companies on their death bed. I realized how much human potential is trapped in failing organizations – people with hopes and dreams who have been sucked into the machinery.

I learned that I love taking what no one else wants and breathing life into it. Like the prisoners. Working on the island of misfit companies is decidedly unsexy, but I find immense pleasure in moving an organization towards purpose and health.

Through all of this work and conversations with great people like Kenyatta, I have realized that our darkest moments are often a sign that things are about to change.  And that leaves us open to a catalyzing event, like a mother’s “tough love” letter or a daughter going away.

We then hopefully realize that the ingredients for turnaround are already in place. And we have no choice but to act. And through blood, sweat and tears, we turn it around.

And then we fall down again. We never check the box on being “fixed.” But the more we pick ourselves up, the stronger those muscles become, and the easier it becomes. And the more empathetic we are to others going through dark times.

You helped do that for me.

So thank you.

To Find Purpose in Your Work, Start Small

Finding purpose in your work is not nearly as easy as commencement addresses would have you believe.

For me, it used to be the bed test: Do I jump out of bed to get after it? And do I go to bed bone-tired but satisfied from doing it? Or would I rather be selling mattresses?

But meaning gets deeper yet fuzzier in middle age, when competence gives way to significance in our priority list, and we wander around asking big, vague questions like, ‘Is this the life I wanted?’ and ‘Am I really going to bed at 9pm’?

Rottweiler And Leash

Why is “the why” so important?

Viktor Frankl answered that question pretty clearly (and before him Nietzsche) in Man’s Search for Meaning where he recounts life as a prisoner in a German concentration camp and how having meaning was the best chance at survival. He then covers his method of psychology (Logotherapy) that revolves around purpose.

This is the bible of why we need a ‘why’ and one of my favorite books. It’s also one of the best “you think your life is tough?” reality checks to read while you scarf down your latte and gluten-free muffin.

“For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s personal dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself.” – Viktor Frankl

But damn, that’s hard to find. And stressful if we don’t find it, especially with all the pithy online inspirationoise telling us to follow our dreams.

Providing for one’s family is enough for a while, but at some point it’s not just about a paycheck when there are other opportunities to meet our basic needs.

I’m aware that ‘professional purpose’ is not a problem that plagues farmers in Nepal. They know their why. But our country is obsessed with it. And with good reason. Without purpose, as Frankl wrote, we get depressed, addicted and aggressive. Our inner lives become a zoo with open cages.

My Experiment

Last time, I tried to hack purpose by pledging half the money I made towards causes I cared about. That helped, but turned out to be too peripheral if I didn’t enjoy the daily grind.

This time, I’m jumping into stuff I love (“following my curiosity” as Elizabeth Gilbert TED’ed about) and hoping it ends up in purpose. And if not, at least I’ll enjoy the ride.

Perhaps purpose is always there, but gets drowned out by all of the useless voices in my head. Instead of being my co-passenger in a nimble sports car, purpose has been quietly reading a book in the back of a school bus full of obnoxious kids.

I’m still a work in progress, but I’m picking up a few things.  

I feel closer to my purpose when…

  1. I get past my own whiny crap (I save that for this blog) and help others. It’s a Hallmark-worthy sentiment, but it’s true.
  2. I have a healthy mix of childlike joy, where I lose hours without noticing, and adult responsibility where I feel like a part of the tribe. I’m like that triumphant-faced dog going for a walk while carrying his leash in his mouth.
  3. I give up trying to cure cancer. I can make a valuable impact on people’s lives doing what I love and being a good person while doing it.
  4. I don’t worry about what others think. This is an easy thing for me to list as a self-help bullet, but profoundly difficult work. Will dig in here in a later blog.
  5. I crave the results. Yes, the journey is the destination, but without a fierce desire for the endgame, the work doesn’t feel as vital.
  6. I am surrounded by people who give me energy, who push me and make me laugh. It makes the ditch-digging parts okay.
  7. I just start doing stuff. The “What Color is Your Parachute” tests are interesting, but jumping in and doing the work is more enlightening.

The Result? 

Well, it’s not like Indiana Jones using his staff to find out where to dig. It’s more like a kid discovering a big, open playground near his house. By opening myself up to curiosity, I found a bunch of new places to play for awhile –  “life experiments.”

Just breathe. Start small. Follow my gut. Find good people.

And then occasionally I step back from it all.

And I’m reminded that maybe I’m relying too much on my professional life for purpose. Like a lot of Americans, I’ve been consumed with one section of a jigsaw puzzle that is much larger than I imagined.

As Frankl writes, we also find purpose in the love we have for others and in how we give meaning to our suffering.

I love my work, but maybe the process of finding purpose there is what leads us to other parts of that puzzle that we never would have discovered.

And that’s all good work.

From Paralysis to Purpose in 90 Days

Recently, I challenged myself to commit to a gig by February 1 (see timer courtesy of Crushpath). My readers sent a lot of great feedback, questions…and a few very concerned head shakes. Some wanted to understand how I’m narrowing and filtering the options so that I’d be sure my next step was the right one. So with full-warning that this post is a bit of a selfie, here’s a snapshot of my process.

Getting to Know the Older Guy

Prior to starting the 90-day timer, I spent some time on what gets me up in the morning. Earlier in life, motivations were pretty straightforward (beer, money, opposite sex, beer), but with age, they’ve become more complicated. After seeing a pattern of ex-execs jump at the next “shiny metal object” job that came their way, I decided to dig deeper in the hopes of avoiding the wrong thing.

In a society infatuated with the self, there’s no shortage of tools designed to help people understand what makes them tick: Enneagram (I’m a 3), Myers-Briggs (ENTP), What Color is Your Parachute (mauve). I was even given a set of purpose cards (worst poker game ever). You could get caught up running self-diagnostics for months, but I think it’s best to pick one or two frameworks that fit your personality. Ultimately I found the most insights by asking myself: 1) When do you feel the most alive and why? 2) What do you want your legacy to be? 3) Who do you “want in the boat” with you?

I’ll spare you the navel-gazing details, but what I learned was this: I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives.

Clarifying and Learning

Once I had a sense of the goal, the process for attaining it seemed less Herculean. I listed out my “Must Haves” (e.g. creative control, dinner w/ family 4 out of 5 weekdays, intellectual interest) and “Can’t Haves” (e.g. long commute, board members who think they know best, overly crowded market).

I interviewed people with similar early careers, but different paths afterwards. People who had been founding CEOs, but had gone on to become venture capitalists, exec coaches, serial entrepreneurs, social entrepreneurs, nonprofit founders, whiskey-shillers, ranchers and confidence men (last one made up). I looked for people who shared my values and passions, and learned everything I could. Then I listed the most appealing options.

Extreme Narrowing

With list in hand, I jumped into a professional dating period that rivaled Warren Beatty in the 70’s. Lots of good people and ideas, but in Silicon Valley everyone wants to be CEO of their own thing. Also, it’s hard to commit to people you haven’t worked with before – and difficult to get two strangers excited about pursuing the same goals.

Realizing the process was taking too long and going in weird directions, I set the timer and committed to focus. Since then, I have become shark-like in my priorities. No meetings that don’t advance the goal. Always aware of my daily tasks. I even set up a war room in my office for managing priorities and scheduling.

War Room from Dr. Strangelove
War Room from Dr. Strangelove

Since then, I’ve only focused on options that get me excited. These could include starting something from scratch (company, social venture, nonprofit, fund), becoming “Founding CEO” for an early-stage start up, and even taking a shorter term executive role to help companies get to the next level (selling the company, raising a round, etc.).

I’m giving each opportunity a rank of 1-5 in three categories: Gut (do I just want to go do it?), Heart (am I emotionally drawn to it?) and Head (does it make sense to do it?).





Next Action


Sample Gig 1




Conversation with Phil K.

In-person working session

Sample Gig 2




Talk to EIRs

Sample Gig 3




Dinner with Veronica and Tom

Facilitating a meeting would be good path

Sample Gig 4




Need feedback from Steve

Option for shorter term work?

Crab Fishing




Rent boat. Sit in it.

For each line item, I drive hard to a decision. If the opportunity remains interesting to me, I’ll take whatever next steps are required to learn more to bring me closer to a decision.

The best filter I’ve found is to work directly with the team involved. There’s no better way to get to know the opportunity than rolling up your sleeves on something together. This is especially true for new careers – if you’re a mailman and want to be a hand model, best to try it out first.

Final Thoughts

I found it helpful to take time away from all the voices. Too much advice can cloud judgment, and often the advice is what those people would do in your situation, not thoughtful insights into your unique path. (But please keep your comments coming – I’m totally listening.) As a culture, we get so wrapped up in what other people think, it can be hard to find purposeful work. We put too much emphasis on personal brand and image over happiness. It’s a shame. Most people are too busy taking their own selfies to care anyway.

You can be as structured about this process as you want, but my experience is that the gut knows best. The more closely I listen to it, the better the options become.