Doubt, a Love Story

Phase 1: "Doubt, I Hate You"

Doubt, you suck. You're boring, draining. You contribute nothing. It's not like you're even funny, or beautiful. In fact, the only thing you help me create are future scenarios that will probably never play out, which get me hyperventilating (and therefore prepping) for armageddon, before breakfast.

So why do so many leaders get caught up with you?

Whether you're building teams, art, businesses, nations or your personal career, doubt works hard to creep in. Doubt begins innocently enough, just a spare question left unanswered. Left unchecked, it grows quickly into an insistent, gnawing stomach ache, the kind that doesn't come about for any physiological reason but as a result of the state that you're in. As a result of something that you're thinking, or telling yourself, based on the meshing together of (likely) unrelated, but stacked annoyances. A few good people flip out about this or that, and don't understand your vision or what you're building. A few others pass little poison pills of skepticism, because it's their job or it's just what they have inside of them. Someone else, moody about whatever. The perfect storm.

Phase 2: "Shut up and Don't be Boring"

It's hard to hear people question what you're passionate about, and struggle to 'get' a vision that is so perfectly clear to you. It's hard to hear people doubt what you believe in, and it's easy to just want them to go away (and take their infectious doubt with them). Whether they're informed or ignorant, eventually, the repetition of it all can stack enough to turn your head and fester. Enter self doubt, situational doubt, doubt in others.

Whatever flavor, lingering doubt is a luxury you can't afford, not even for a moment. Listen to the underlying questions in case they're helpful to you, but leave the struggle bus behind. When you let your head turn towards something that doesn't serve you, something that's the result of someone else's worry you are quickly seduced down a boring, destructive path as you steer in the direction of your focus. And this state can make you boring and destructive, sucking minutes, days, years from you, and leave you with a view of the world and your situation from which it is no longer possible to reach for great things. And it can distract you from what you need to be focusing on, and start taking up real estate in your mind. Not to mention, making you the kind of person people avoid at cocktail parties.

Every leader goes through this, every single one. No matter how awesome your company is, what your traction has been, or how brilliant your team, things will go wrong, people will sit there poking holes, the world will change and there's nothing you can do about it. Others will tell you not to take any of the lows personally, but good luck with that. It's hard to have a soul about what you do, to love it with everything you have, and be able to simultaneously uncouple your feelings from the annoying stuff. Your feelings keep you engaged, compelling and passionate and I've yet to meet a great leader who can stay completely objective and detached under fire. But none of this can control you. It's easy to forget that you are not your worrying mind.

The best advice I can give, that was given to me, is to fill up your war chest before you meet the world, and continuously fill it. Not just with money, but with all the reasons why you love what you're building, and why you love your company. Lock yourself in a comfortable place where you get inspired, and write down everything you can think of - from the big lofty things like how you're changing the world and making lives better, to the little specific moments when a client said something that made you happy, or proud. What you loved about the first time when someone really 'got it', or when you realized you were on to something bigger than you could have imagined. The excitement of it, the deep sense of purpose and contribution that brought.

Recall clearly, that first moment when you glanced up from all the chaos and realized your company was supporting families, and that this product you dreamed about in your living room would one day be putting kids through college, or paying for loved ones in faraway places to have better lives. Enumerate for yourself all the million tiny details that you wish everyone knew instantly about you and your team, without having to be skeptical first or to put you through some annoying ringer. How much you value diversity, how brilliant the people are, how you've never met people more fiercely competitive, and also so kind, authentic and creative.

The first time I went through this exercise (guided by numerous beautifully crafted, essay-length text messages from a dear friend of mine), I spent an hour alone on my rooftop and wrote down one hundred things, barely taking my pen from my journal. The unsolicited (but appreciated) texts came through in perfect time to bring me back to myself, just when I was starting to let other people's doubt turn my head. It was the most invigorating thing ever and I felt instantly new again.

Focusing back on what I love, meant that I shifted my attention to all the good stuff. There was so much of it - my team, our fabulous clients, how awesome our product is, what I'm so proud of about our culture. When I read everything back (which I suggest you do often) it became so clear to me that in the end it all comes down to people. For every one thing I love about what we've built, there are at least ten things I love about our clients and the people who show up every day, and make our company a great place to work at.

I learned also, that the culture you've built is such a personal reflection - and this carries risk with it too. Because my good habits are the good habits of my company, but so too are my bad habits. Like not celebrating success, moving right on to the next milestone or the next challenge, and allowing all the juice of the journey to pass me by. Like not remembering how much I love and honor each and every messed up moment, because each new thing that happens makes us better, and stronger, and more equipped to tackle what is coming our way in the future. If we're not changing faster on the inside than the world is changing on the outside, then we're dead - and moving this quickly means screwing up routinely on all fronts and getting your ass handed to you on a regular basis. The opposite, complacency, is the true enemy.

Phase 3: Doubt- I love you, thank you

So, learning to love and embrace the doubt is all a part of this process. Doubt can keep you sharp, hungry, urgent. Love it, embrace it, thank it for sharing. But remember that it doesn't own you, that it's a mind-hack intended to serve you and your team but nothing more.

So when someone you respect is panicking around you or telling you the sky is falling, or if several bright people begin poking holes in your vision or what you're building, breathe and (internally) thank them for keeping you sharp. Listen to the words, hear the meaning and hold them up for questioning, but don't let this fester. Re-read a few of the things you wrote down about why you love your company, your product, your team. Allow yourself to feel good, remember that it's all a part of the process. Remember why you're here.

And then get back to work, because you don't have time to dwell on anything that isn't making your customers happier, your product better, or otherwise creating value in this world.