On Becoming a Thought Leader

I’ve been thinking a lot about the concept of hard work and on becoming an expert.

Unsurprisingly, there is a lot to it.

Hard Work

Last summer I read Malcolm Gladwell’s Outliers. A fascinating book for anyone to read. One of his points is that it usually takes us 10,000 hours to become an expert in a field. Whether a pianist, third-baseman, wine sommelier, or an expert in some area of SaaS, hard work is required. No substitutes. 


It’s not just hard work. I can do the same thing over and over again, and not learn why something works the way it does. I may know how gravity works (things fall), but if I don’t understand why it works, then it makes it harder to make predictions for something new (like filling a balloon with helium). In the same way, focus is required. It’s not simply enough to expect after years of hard work that you will be recognized as an expert. 

Without focus, the winds will blow you in many directions. Read Shane Parrish’s article on Understanding Speed and Velocity: Saying “NO” to the Non-Essential. Cut out non-essentials.
We’ve been told that learning to say “no” frees us up to do more. We’ve been told “less is more.” If you don’t learn to say no, then your thought leadership quality will be watered down. It’s not simply the 10,000 hours. It’s a ruthless pursuit of the goal. We can share all of the quotable lines from big names, but until we do this very simple thing, we won’t get far.

Develop it into a habit. Add it to your to do list (yes, right now). Review your project list and delete what doesn’t make sense. Then move everything you’d like to do to a “someday” or “back burner” list. Get it off your priority list — you’re only stressing yourself out. 

Another word for focus is sacrifice. You must cut out things that you like for the things you love. Saying yes to everyone outside my house inevitable means no to my health, my rest, or my family — all of which should be at the top of the list, not the bottom. Learn to say no. Focus on what matters. It’s difficult for us to say no to coworkers, friends, and even ourselves. Saying “yes” to all these things means “no” to your dream.


You can be amazing at something but not be able to communicate well. Communication requires a significant investment in reflection. 

“If a tree falls in a forest and no is around to hear it, does it make a sound?” is an interesting philosophical question, and also insightful for the parallel of communication. If you work hard and are focused on the true results, will you be an expert in the field? Well, yes. Because you will be an expert in your field, but may not be recognized. This is where you make the choice. The answer isn’t simply “yes” to learning to communicate your thoughts. For instance, that can detract from a lot of research you’re doing — but it can also help frame concepts you’ve been thinking on, but couldn’t articulate till you put pen to paper. Even if you do that, there’s no reason it must be in a public forum rather than your private journal. Writing does not necessitate public discourse.

There are many avenues to becoming a thought leader. There’s the obvious ones — blogging, vlogging, podcasting, speaking, social media — and there are others that are not as obvious. Don’t allow the “sexy” methods to pull you from the effective ones. They are often mutually exclusive.


There are a lot of us who want to specialize, become experts, and contribute at a higher level. We don’t settle for mediocrity or simply copying content from others (besides the ethical reasons). All of these are worthy endeavors and ought to be pursued. 

The next step is a tough one. It is this: to evaluate the merits of this list not because of who wrote it or was referenced in it, but on the ideas, the concept, and the truth. By shortcutting the process and evaluating it on any other measures (author recognition, friend’s reference, etc.) is merely proving you have a long way to go in being a leader in thought. 

Additional Resources

Efficiency: A Letter to My Younger Self

Oftentimes and many years later we have realizations on how silly we were, how short-sided we thought, or simply how wrong we were. This is one I wish I could write to my younger self. As I journaled, I realized it wasn’t simply a letter to my younger self, but to many, many people today. A lesson widely needed.

I understand you want to be as efficient as possible. In fact, you want everything in your life to be as efficient as possible.

I think that is to your downfall and here’s why: efficiency is not the goal, effectiveness is.

Peter Drucker in his masterpiece The Effective Executive talks about this specifically. We need to be effective, that is the goal. And one concern I have with what you’re trying to do is you’re trying to squeeze every last penny out. You need to leave some money on the table. That is not a bad thing to do.

For example, if you onboard employees as quickly as possible with as little training as possible then you will get what you paid for. You will get a bad product. And you will have to pay for that for months and possibly years to come.

If you try to write up a big process real quick, give it one quick glance, and hit “send”, then you will find things you should have considered.

When you need to reconcile the accounting books and you “just want to get through it” because you have many other clients to work on, don’t be surprised when your errors get caught in review — and you look bad.

Don’t be shortsighted by the “wins” of today at tomorrow’s costs. Instead, invest today for tomorrow’s gains. Just like we need to get enough sleep each night in order to be effective, if we chew into tonight’s sleep to get a bit more done today we will waste the entire tomorrow. There’s no such thing as a free lunch.

Just because it’s easier to measure efficiency doesn’t allow you to take the lazy and less productive way. Go the more difficult and rewarding path. Go for effectiveness and win.

The Two Pennies

I went on a jog a few days ago. No earbuds. No screens. No music, audiobooks, podcasts—just my thoughts. I enjoyed the beauty of January, though we often think of it as dead and decaying. We long for spring.

Around 3 miles in I looked down and saw two pennies. I picked them up for my kids (I knew they’d be excited at the prospect of “having money”). Typically, jog for me means catching up on podcasts, listening to that audiobook, etc. It’s often about checking another thing off the list. Arguably this jog was 0% productive since I couldn’t check anything off my list. However, it cleared my mind. I thought at a different pace since I was focused on what was around me, such as noticing two pennies that I would never have seen before. I reframed worries and doubts that had grown colossal. I thought through opportunities that seemed out of reach. I realized many projects were neither important nor urgent, so I could put them to the back burner.

So while I’ll continue to listen to podcasts and audiobooks while jogging, I won’t do it all the time. Sometimes you need to spend an hour to reflect and absorb what you already know, to make those connections to things you’ve never made before. In short, don’t only ever put on your headphones to block the outside world, sometimes sit (or jog) and listen to that around you and your own thoughts.

Just my two cents.

If All You’re Doing Is Surviving…

Below is an example from my life about parenthood, but the principles to this story can be applied to all areas of life—work, school, volunteer, or whatever. If you’re struggling as a parent, it’s okay. We all are. Secondly, reach out for help—I do the same. We are that village that takes to raise all of our kids.

It must be a popular statement, or else it simply sticks out in my mind because I’ve begun to notice it everywhere. Here’s how the conversation usually goes:

Friend: “How old are your kids again?”
Me: “Their ages are…”
Friend: “Oh wow. Yeah. You’re just surviving. That’s all you’re doing right now.” (emphasis mine)

While I appreciate my friend’s compassion and validating my attempt at being a good parent, I’ve begun rethinking this line.

It’s not just one friend, either. It’s family. It’s many friends. It’s coworkers. The difficult thing is just that: so many people tell you this as a parent with young kids that you just accept that’s how life is.

But then what are you supposed to do? Bide your time until your kids grow up a little bit? Then you’re busy because you’re running them from school to soccer practice—oh, shoot! Then picking up the other one for ballet and then a quick bite to eat, home for homework, and finally exhausted on the couch! Then repeat the next day.

If you need to get past that period of life, then what? Teenagers? Ugh. I don’t even need to go there!

So if you’re just surviving with young kids, frazzled with being a soccer mom, and finally teenagers, then what? Wait till they’re out of the house? By then you’re in your 50s and thinking of retirement, grandkids, and if your bones weren’t hurting in their 30s (mine are) then your 40s and certainly your 50s.

There are no easy answers, only deep, soul-searching questions. But for those of you who are just surviving, I must ask the question, “what are you surviving for?” Are you surviving so that you can work to make the world a better place? Just to get by and hope bad vibes stay out of your way? So that you can live to see a concert, achieve a goal, unlock a quest, or see your kids attain _________? Is that it? Is that all?

We each have varying levels of hope for the future. Some are distraught, some are depressed, and some are optimistic—and some are in between. The purpose of this thought isn’t to be a depressant, but to awaken our souls to these questions. I’d rather go through life asking difficult questions that I may never get the answers to, than to idly sit by too afraid to open the door.

So, to those who have a family member with cancer. To those of us who are workaholics. To those of us who are in over their heads with debt. To those of us who can never seem to catch up. Who feel as if they aren’t even a half-way decent parent. Who feel like failures as parents. Who are cancer survivors. Who can’t catch a break. Who have recently lost a child, parent, spouse, or close friend. To those of us who simply feel like we’re only surviving. Here is the message: there is hope—we just spent a month sharing the Christmas story. Read it (the real version, not the fluffed up Santa version).

However, even if you’re not religious (or don’t want to discuss it), spend time with a close friend or family member. Deepen the bonds you have—or feel like once had—with that person. Shed your toxic relationships. Get away and reflect on your last year. It’s not going to be easy. But go on a walk, let it out (cry, if needed!). You can’t move forward in life if you disallow yourself to share with others and yourself. Be willing to reflect on your past, current situation, and dreams for the future. If you do that, you may find that all you’re doing is surviving, but maybe, just maybe, you’ll begin to find hints of meaning.

Reflections on Robinhood’s checking & savings fiasco

We in fintech often confuse Type 1 vs 2 decisions—reversible/not reversible. Robinhood reversed it, yes, but at high cost. As great as tech is, disrupting existing systems first requires wading through minutiae of regs + history.

It’s truly amazing to be part of companies and watch other companies move fast and do incredible things. And perhaps if I were on the Robinhood team I would have come to the same conclusion they did (our hubris will convince us we would “never have done ____________”), but these stories still illustrate to us several key principles:

1. Moving fast is high risk. If you can stomach that risk, great. But be prepared for some decisions to blow up in your face.

2. Ask for counterpoints. Groupthink is deadly. Ask counterpoints from those who agree with you will give you exactly what you expect — not much. Solicit from those who disagree or are willing to disagree.

3. Conduct pre-mortems. While not bullet-proof, when we’ve conducted a pre-mortem (assume your action will fail, and discuss why it did) to poke holes. This helped us identify many of the core issues we would inevitably face. Instead of concluding that “yes, this is awesome” we were able to comprehend, “yes, this is awesome, but _____________” to have a sober, realistic understanding of the land mines that lay ahead of us.

4. Execution is important, but pre-work is even more so. Think of it this way: if you give a presentation on a topic you’ve never spoken about before, where do you spend more time: preparing for your presentation (thinking, slide creation, rehearsing) or the actual presentation?

Sleep on it. I’ve been part of countless decisions where we did “research” (usually about 20 minutes or less). If we only had dug a little bit deeper, we would have realized some glaring issues.

5. Lastly, humility. You are human, you’re far from perfect and you are certainly not invincible. Be the leader who admits they’re wrong, don’t be the leader who is incapable of that.