The hard way is the fastest way to growth

The vital role of pain in becoming a better leader

Welcome entrepreneurs.

I’m so glad you’re here.

Over the past two weeks I’ve been virtually traveling the world, talking about the Dark Side of Crushing it with folks in Detroit, Berlin and the Middle East. If you missed it, check out the link to my interview with Startup Grind (incidentally, if you’re morbidly curious as to what Laura and I might have been like in 2015, here’s our previous interview on Startup Grind, too. Yeesh), and my talk with Invest Detroit Ventures will be posted soon.

You’ll also notice that things are changing a bit around here. The format of the newsletter below has changed (feedback is appreciated), as has the Inside Out corporate website (and, soon, logo). My work is growing up, and I am more grateful than I can say that you all have given me this platform, this opportunity, to help change the narrative around building companies.

At its core, leadership is a profound opportunity to express your one unique life in the world. From my perspective it’s high time we treated it as such. Thanks for helping me change the narrative, one leader at a time.

Let’s dive in.

How leaders grow into who they want to be

The path of leadership is one of change. Of growth. That’s why I love the work of coaching so much. I get to accompany incredibly talented and driven people on the journey through the wilderness and mess between who they are, and who they want to become.

Most leaders, they think that this is a thinking exercise. That change is simply a matter of deciding what we want and then systematically working toward it. As comforting as it is to think of ourselves as these incredibly logical, empirically efficient creatures (particularly as we make decisions with millions of dollars and hundreds of jobs in the balance), unfortunately that’s simply not the case.

Reams of neuropsychological research (here’s a decent summary out of Harvard and Carnegie-Mellon) indicates that people, even the most calculating leaders, make decisions emotionally and then rationalize that decision with logic. In other words, what we now know empirically is that the work of our conscious mind is to rationalize, not to be rational. And so it is with change. It’s not enough to logically understand the benefit of change — we must also reach the same conclusion emotionally.

This is relatively straightforward. When change happens, it’s because changing feels better than staying the same. Simple as that. And then afterward we come up with logical reasons in support of the change.

Simple yes. But this is an incredibly high bar. We’re evolutionarily wired to prefer the status quo because no matter how bad it is, we know we will live through it. We can of course take steps to make changing feel better — visualization, the law of attraction, etc — but overcoming our evolutionary bias against change is often too difficult, and we end up frustrated despite our at times herculean efforts.

When change does finally happen, it’s most often the result of pain. Whether that’s the physical pain of touching a hot stove, or the emotional pain of having our work rejected by a customer or investor, we change most effectively and reliably when staying the same hurts too bad.

“We can ignore even pleasure. But pain insists upon being attended to.”- C.S. Lewis

Great. Pain drives change. Pain still sucks. So what?

Understanding this, we can take an active (although unpleasant) role in our own transformation.

The reason that so many leaders evolve slower than they’d like, is that humans don’t like pain. So when the pain comes we look away, numbing ourselves to the very catalyst to our transformation. We might ignore the pain of rejection by quickly jumping to the next task, or distract ourselves from the pain of an unworkable co-founder relationship with TV or food. We might just shove the feeling down in the name of “compartmentalizing” (downsides of that approach detailed here).

And in so doing we stay comfortable, and stuck, robbing ourselves of the transformation we say we want. We don’t evolve, not because it’s actually comfortable where we are, but because we aren’t willing to face the actual pain of our situation. To feel it, unmitigated, without reflexively looking away.

It’s normal to avoid pain. It’s part of the evolutionary wiring that lead to us being here to talk about it. Pain sucks, and it makes sense to avoid it in most circumstances.

But if you’re trying to change, to grow, as so many leaders are, the specific pain caused by your current situation can also be an incredible catalyst for change. If you welcome it.

If you’re playing to win, all of life is an obstacle.

If you’re playing to grow, all of life is an ally.

“Life is a thorough university; pain and hardship are its distinguished professors.” ― Matshona Dhliwayo



One: Savor what you dread and avoid (Zen Habits)

If this week’s essay resonated with you, consider that you can lean even further into your own transformation by learning to savor your pain. To most people this sounds awful, but when I left my last company I experienced this in my meditations on the pain of leaving that part of my identity behind, and can say from experience that it changed me. Leo Babauta from the hyper-popular blog Zen Habits gives a great example.


Two: WTF is going on with #GME (Various)

The news of the week is what r/wallstreetbets did to hedge fund manager Gabe Plotkin. TL/DR: Plotkin heavily shorted GameStop stock, betting it would go down, so “retail investors” AKA “Trader Joes” organized on Reddit and bought a ton of the stock, spiking it and costing Gabe and other professional investors literal billions in a day. The interesting part is what happened next, and its implications. Here’s the best synopsis I’ve found on the Internet so far, if you’re wondering what this all means. And this from Detroit financial media company, Benzinga, on what Mark Cuban and others are saying, and this from Union Square Ventures’ Fred Wilson. (And, lest you get excited and want to jump into the wave pool, here’s a warning from experience).

Three: How the best leaders answer “what are we here for” (HBR)

In this analysis of how the best leaders drive meaning throughout their organizations, Harvard Business Review found that the most effective leaders co-created their org’s meaning along with the stakeholders affected by it. Longtime SMS readers, this should be familiar.


Four: How leaders kill meaning at work (McKinsey)

And the flipside. Supplement your work on driving meaning throughout your team with McKinsey’s overview of four common, yet very avoidable traps that kill meaning in your employees.


Five: The dark side of authentic leadership (Forbes)

Business psychologist Tomas Chamorro-Premuzic, finally fed up at all the authenticity bubbling up around him, published this opinion piece about The Dark Side of Authentic Leadership. It’s worth a read, if only because it’s good hygiene to read the opposite of your ideas, but ultimately the argument rests on an assumption that I’ve found to be false: that people’s authentic selves are inherently ineffective and must be filtered to get more than “4 to 5 people to at least tolerate” them (the author even goes as far as alluding that people’s authentic selves are bad, using Hitler, Stalin and Mao as the examples).


Finally, I’d love to hear how you feel about the new SMS format. If you like it, or you hate it, either way please let me know.

Be well,


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