The forgotten half of leadership

Leadership is to most a matter of doing. People have written reams of books, articles, whitepapers, etc about all the doing that is required of leaders. Setting the vision, building a culture, fundraising, all about doing. It’s a concession to our pervasive culture of productivity that the only part of leadership that is talked about is the part that looks like a bunch of boxes one can check. It’s what’s measurable, so it’s what gets done. But it’s only half of the battle.

Leadership necessarily involves two equally important aspects: the subject and the object. We focus so much on the object, or the output, that leaders should strive for, that we rarely address subject, or the leader herself.

This may seem like another way of saying “sharpen your sword,” but the practical reality of doing that is really just a way of checking another box. Important, for sure, but still in the category of the object.

What is needed is a sincere and equal focus on the leader herself, or more specifically the place from which the leader is coming.

Every box that a leader checks is checked from a very unique perspective, and that perspective includes specific preferences, biases, traumas and neuroses, which together make up the narrative that leader has built to bring order and meaning to her life. These biases, traumas, preferences and neuroses, all the chatter living in her head whether consciously or not, are the overarching framework through which she decides which boxes to check and why, and what it means to check a box. Everything that a leader does in her quest to bring about a result for her team, and the things she decides are valuable to do in the first place, are inextricably driven by the internal discussion going on in her head.

If she has overcome a rough childhood, she is more likely to hire people who persevere. If her parents were members of a labor union she is more likely to prioritize creating a great culture over driving for additional profitability. And so on.

None of this is bad, inherently. It’s just a matter of consciously making these choices, rather than letting unconscious processes make them for you. The problem is that every leader makes decisions based on a set of criteria and influences which are unknown to her, unless that leader has done some serious internal work.

The work, here, is to dive deep into your own thought processes, to see the patterns for yourself. Figure out your own innate biases, and what environmental triggers send you down specific thought patterns. Once you see them, then you have a choice to make: are these helpful to my aim as a leader, or should I work to neutralize them.

This is why the best leaders tend to be meditators, and the best business coaches have backgrounds in psychology.

In becoming the best leader you can be, it’s important to become adept at vision setting, culture building, selling, fundraising and the rest. But as leadership is about making good choices, not only for you but on behalf of all the human beings for whom you are responsible, it’s equally important to do the internal work to figure out why you make the choices you make in the first place, so you can make them consciously.

If you want to help people, start a business, not a nonprofit

At some point most, but not all, successful people figure out that no amount of success or money will actually make them happy, and at that significant turning point, people start to look for meaning in different places. There are a lot of places to turn, as the human animal can make literally anything meaningful, but the best of these people turn to helping others.

If you haven’t done a ton of helping others up to that point, it can look like the non-profit world is the route to take here, as it seems like common sense that helping people is why nonprofits exist. That’s fine, and many great people work in the nonprofit world, but if you’re looking to really help people it’s the wrong direction.

Charity is a very small pond.

If you add up all the charitable giving in the world, including all the endowments, the foundations, the $18 to Bernie Sanders’ campaign, literally all of it, it all adds up to 0.005 of the world’s spending, a number which has been relatively steady the past 50 years. A half a percent.

Bracket out for a second the moral statement that level of species-wide charitable investment makes, and let’s just focus on the practical implications for someone really looking for the best way to help people. Absent running for public office (which godspeed to those souls who jump in that water but I have both no interest and a checkered past) we basically have two choices: business, responsible for 99.5% of all monetary impact in the world, and charity, responsible for 0.5%. Remember the all-importance of market size, and choose to fish where the fish are.

If you still think a nonprofit is the way to go, consider that since there is not enough money to go around, and since there are over 1.5 million registered worthy causes in the US alone, in order for you to make the impact you want to make with your nonprofit, you have to literally take funding from another nonprofit with another well meaning mission to change the world. People or organizations with money and a conscience tend to organize their giving by first setting a budget, and then choosing where to give or which cause to support from that budget. So if your neighbor wins and gets funding, that actually in reality lowers the chances of you getting the funding you need. Charity is literally a zero-sum game, so there’s a tangible human cost to any success you have in that area. Not the case in business, in which there is absolutely such a thing as a win/win/win situation (despite, admittedly, some confusion).

So far as I can tell, the only way to create lasting meaning for human beings is to help other human beings. For those of us who have learned the emptiness of self-serving success and want to create meaning by helping others, start a business, not a nonprofit.

Risk vs Fear, Ryan Vaughn on Creative Mornings

Finding myself explaining the distinction between Risk and fear a lot recently. Risk is a reality of life which is present in nearly everything we do, particularly for those of us starting or running companies, while fear is an emotional reflex that takes over our nervous system and often leads to, among other things, poor performance.

Risk is real, fear is a reflex. More often than not they have nothing to do with one another, but when confronting a situation we conflate the two all the time.

I put together a talk about this topic a couple years ago. It was the first time I shared my time in jail in a public setting. I was terrified that I would be ostracized if people found out, but in reality sharing that fact had absolutely no negative impact. It did, however, bring me closer with our team.

I almost didn’t share it because of the fear, but I’m glad I did. It’s one of the best talks I’ve given.