Where the best mission statements come from

And an exercise to unlock hidden potential within your work

Welcome Entrepreneurs. I’m so glad you’re here.

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Going through some challenging cultural times with my previous company back in 2015, I vividly remember reading nasty reviews on Glassdoor from employees as they walked out the door. It truly rocked me. I put so much of myself into creating VNN into a place that I hoped people would love as much as me, so it hurt deeply to hear that some didn’t.

But that pain caused me to reflect. It showed me how I was not living up to my responsibilities as a leader, and catalyzed the changes that helped us rebuild our corporate culture into an amazing place to work. I got to reap the benefits of that cultural turnaround for years, and still count it among my proudest achievements as a CEO.

And then, years later as VNN continues to take over the HS sports market without me, I get this note from a former employee:

Wow. Considering the Glassdoor reviews that started it all, just wow. This is quite the gift. Things like this make my work feel more worthwhile than any milestone I could hit. Thank you, Alex.

A founder getting clear on her purpose and values can have a remarkable impact on her organization. This week, I want to talk about an important question founders can ask to gain that clarity.

Hope you enjoy.

An exercise in purpose

"What is success for you?  And how will you know when you have it?"

These are among the first questions I ask founders when I work with them, and it took me a while to stop being surprised by the deer-in-headlights looks I see in response. That would have been me five years ago, but now I operate with a much clearer vision for myself and my life. In the process, I’ve managed to forget how often other people work hard without a sense of why they’re doing it.  Not just what goal they’re working toward, but why it matters in the context of their lives.

The stakes are high, as we spend most of our life chasing one goal after the next, many times thinking that each milestone is significant and will give us more than just a quick dopamine hit. Unfortunately, as I learned the hard way, you can spend a decade running at top speed, egged on by a culture that deifies productivity, to a destination that ultimately doesn't make you happy. As Charles De Gaulle said, "the cemeteries are full of indispensable men." 

What success means and how much is enough are challenging questions to answer. These questions force us to wrestle with the fact that we're literally spending our lives on the thing we're doing, and that both will at some point end (the thing and the life). 

“What is success for you?  And how will you know when you have it?”

Founders usually answer this question in terms of their businesses. Success is getting to the next financing event or hitting $10m in revenue.  Success is, ultimately, an exit. It's easier to grapple with the ending of your business than your own mortality, and by the time most founders come to me, they’ve already been forced to identify and clearly articulate the goals for their businesses, if for no other reason than to raise capital from investors. So because there's some muscle memory with regard to articulating the meta, big-picture goals of their businesses, founders first fall back on that when asked to confront the big questions. 

Articulating your goals in such a way is normal in the highest levels of business because it works. It’s vital to "begin with the end in mind," as Stephen Covey has said. Knowing exactly where you're going as an entrepreneur is foundational to making progress, whether as a solo-preneur or a leader of teams-of-teams. 

But in my experience it's rare to apply such rigor to the real big picture: our lives. 

It’s rare to think with such intention about how we want to spend our one wild and precious life. A life in which many businesses may occur. Not because it's not effective -- knowing where you're headed has the same catalytic effect in any context -- but because it's a hard question, and outside the context of your business it's a question that you’re rarely forced to answer.  In our myopic growth culture, opportunities to contemplate endings are precious and rare.  At least for healthy people.  

“What is success for you?  And how will you know when you have it?”

That's why I ask. Because these are the types of questions that few people will ask themselves.  Because our conversation forces them to grapple with the temporality of their lives—the fact that they will end at some point. And because very few people want to go there alone. 

It's uncomfortable to ask, because I know where these questions lead. But I ask anyway because I know what can happen to a life if the answers aren’t clear. It's what happens to most lives in the world today: they are spent chasing the thing that everyone else seems to want, only to attain it and realize it wasn't worth the wanting. 

"I, too, am a log, and I am already burning. Every cell in my body is using oxygen to produce energy, just like this fire in front of me. And when my fuel runs out, I will die, just like this fire will die out. I am being consumed by the sacred fire of life. I have no choice about that. But I do have a choice about the altar on which I place myself. To what will I offer myself? I have put myself on the altar of such unimportant material and egocentric things. It is time to make a deliberate choice and start burning on the altar of meaning, love, and freedom." -- Fred Kofman

I know because I spent fifteen years as a tech CEO, running after the economic success and prestige I thought would make me happy. I got the success and prestige, and wondered what was wrong with me that I wasn't happy. There was nothing wrong with me, I came to realize. I just didn't really want the things I thought I wanted. With fifteen years of momentum driving me forward, it was incredibly painful to step off the path of money and fame, figure out what I really wanted out of my one, precious life, and reorient toward that. 

The Summer Day, by Mary Oliver

Who made the world?

Who made the swan, and the black bear?

Who made the grasshopper?

This grasshopper, I mean-

the one who has flung herself out of the grass,

the one who is eating sugar out of my hand,

who is moving her jaws back and forth instead of up and down-

who is gazing around with her enormous and complicated eyes.

Now she lifts her pale forearms and thoroughly washes her face.

Now she snaps her wings open, and floats away.

I don't know exactly what a prayer is.

I do know how to pay attention, how to fall down

into the grass, how to kneel down in the grass,

how to be idle and blessed, how to stroll through the fields,

which is what I have been doing all day.

Tell me, what else should I have done?

Doesn't everything die at last, and too soon?

Tell me, what is it you plan to do

with your one wild and precious life?

So I keep asking the questions.  To others, and to myself. 

"What is success for you? And how will you know when you have it?" 

And I keep pressing when I hear the well-practiced answer about a founder's company, because it's worth remembering that a company occurs in the context of a life, and not the other way around. Even though sometimes it seems otherwise. 

An exercise to find your answer

Identifying your purpose, the "why" behind what you're doing as Simon Sinek would say, is tough work.  It's easy to reach for the comfortable, socially-appropriate answer, but to uncover the deeper, more lasting answer to this question, most of the time it's helpful to have a bit of structure to lean on; a ladder to help with the descent. 

My favorite of these ladders is the Eulogy Exercise, which I've adapted from Fred Kofman's The Meaning Revolution. If you're open to grappling with questions of life and death and purpose (and no shame if you're not, yet), I invite you to grab a pen and notebook:

Eulogy Exercise:

Imagine that you are at the end of a long and rich life. You’ve accomplished everything you wanted, behaving honorably and building meaningful connections with your family, friends, and colleagues. You are proud of yourself for leaving a great legacy, and for having led an organization that brought great value to the world. You’ve done your work here, and you feel ready to go. So when you learn that your days are numbered, you take the news in stride. A lot of people who appreciate and admire you want to pay their respects, so they organize a ‘living funeral.’ (A living funeral is a celebration in which a living person with a life-limiting illness listens to the eulogies, praises, and farewells of family, friends, neighbors, and colleagues.) In the ceremony, a dear friend will stand in front of the audience and read a eulogy.

  • Instructions:

    • Write the eulogy that you would like your friend to give.

  • Guidelines:

    • Spend at least 20 minutes journaling your answer without stopping to edit, or even to think. Let your stream-of-consciousness be your guide (no bonus points for good grammar and spelling).

    • It can be helpful to do this exercise more than once, with a week, month or many years between sessions.

This exercise has a way of illuminating your personal North star, if you are honest. So be honest. But please, don't be humble. Don't be socially acceptable, don't be customary, and don't settle. If a thing is possible for anyone in the history of humankind, it's possible for you. And you don't get another chance. You have one life, and in sixty years or tomorrow that life will end. 

What is success for you?  And how will you know when you have it?

(HT: Julie Mosow, Bennett Green, Miranda Newman, Joel Christiansenand Compound for editing!)

PS> If you decide to take on this question, I would love to hear about it. Specifically, what did you learn?

I’ve found it can be quite transformative, and I hope that is your experience as well.

Liked this article? I’d be honored if you’d share with others who might find it valuable. 


Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


One: 2020 Letter to Shareholders (Jeff Bezos, Amazon)

I’m never sure whether to admire Bezos or not, and why. I’m conflicted on this. But I was struck by the importance of a portion of his letter to shareholders, presumably the last he will ever write. It’s worth reading in its entirety, but here’s my favorite part:

“What I’m really asking you to do is to embrace and be realistic about how much energy it takes to maintain that distinctiveness. The world wants you to be typical – in a thousand ways, it pulls at you. Don’t let it happen.

“You have to pay a price for your distinctiveness, and it’s worth it. The fairy tale version of “be yourself” is that all the pain stops as soon as you allow your distinctiveness to shine. That version is misleading. Being yourself is worth it, but don’t expect it to be easy or free.”


Two: Writing as a distinct form of consciousness (Bookbear Express)

I write about 2,000 words/day, most of which I never publish. Most of my writing is for me, and serves much the same role as meditation. Maybe a combination of meditation and executive coaching. I’ve considered writing a post about how well my journaling has served me as a leader, and Joan Mitchell’s post helped me see what I’m doing from another perspective. “The feedback loops of physically typing and looking at the words as they are thought and appear in letters constructs my thinking as it is thought.” Yes. This. And this unique form of consciousness is more effective in many ways than traditional thinking.


Three: Psychedelics 101 (Tim Ferriss’s blog)

Psychedelics changed my life. They expanded my understanding of the Universe. They taught me how to embrace one of the scariest parts of myself — my addiction. And they played a significant role in my post-startup recovery, and helped me understand why I truly am, and always have been, enough.

I haven’t talked about this part of my journey publicly. I may soon. In the meantime, please see below for a great starting point (I suggest starting with Pollan’s book How To Change Your Mind):


Four: Healing in the Deep Ocean of Grief (Mindful)

A entrepreneur friend of mine, Bryan Welch, CEO of Mindful Magazine, wrote a heartbreaking piece about the death of his son. It spoke to me at a deep level, as I suspect it will to many who have done some amount of inner work. This part hit me hard:

“Eventually, of course, there was healing. The pain subsided. Old emotional comforts and habits showed up. I sensed myself subconsciously rebuilding the protections I once had against the sadness and pain in the world.

“And to my surprise and confusion, I wasn’t sure I wanted that to happen.”


Five: Calculating Leader Leverage (Feld Thoughts)

Silver bullets are rare, but this hack might get close. As your company scales, problems get more complex, and it can be a nightmare diagnosing the cause of interpersonal issues. If you’re wrestling with one such issue, Brad Feld has a take that is worth your time to explore and implement.

TL/DR: Do an NPS survey to your employees about your company. Those who score low likely fall under problem managers.



Start Close In

— By David Whyte

Start close in,
don’t take the second step
or the third,
start with the first
close in,
the step
you don’t want to take.

Start with
the ground
you know,
the pale ground
beneath your feet,
your own
way of starting
the conversation.

Start with your own
give up on other
people’s questions,
don’t let them
smother something

To find
another’s voice,
your own voice,
wait until
that voice
becomes a
private ear
to another.

Start right now
take a small step
you can call your own
don’t follow
someone else’s
heroics, be humble
and focused,
start close in,
don’t mistake
that other
for your own.

Start close in,
don’t take
the second step
or the third,
start with the first
close in,
the step
you don’t want to take.


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