Dear Elaine circa 2005,

If you’re reading this, it’s because time travel becomes possible and someone has been kind enough to relay this message to you. Please thank them for me too.

First, it’s Elaine from 2012. In 2005, you are enjoying team walks to Peet’s each morning, realizing that your London and Italian cohorts are right – MSN is huge internationally, and maybe you’re even backing down from your stubborn use of camel case thanks to your friends knocking some sense into you. You’re a motley, passionate start-up crew and that crazy clash of perspectives has made Meebo’s product and team stronger. There are very few occasions where I’d confidently stop time to experience a moment indefinitely. However, that oh-so-short walk to Peet’s is one of them.

I’m not going to spoil your Meebo journey. I wouldn’t want to ruin the exhilarating surprises and nothing I could say, unfortunately, could prevent the occasional soul-crushing despair. Fortunately, the good days will definitely outnumber the bad. However, time travel is an extraordinarily rare opportunity and I know you’d be disappointed if I didn’t offer you any advice.

But please be patient, I want to recount a story from our autobiography…

In an airport between flights, your future Elaine meets a retired psychologist and after some social banter, you casually ask, “So at what age do most people become self-aware — demonstrate an understanding of their strengths & weaknesses and some idea of how they fit into their social context?”

This is a set-up. You’re already thinking about follow-up questions. Does self-awareness gradually increase with age? Is there a time when it peaks? What happens when someone becomes self-aware at the age of 80 – is that even heard of?” You’ve been dying to ask these questions forever.

But what he says stops you, “Elaine, I can’t answer that question because less than 5% of people get there… ever.”

To my 2005 existence, I’m so sorry – I know this is a shock. When you were in middle school, your mother reassured you that your classmates might grow up and surprise you some day — she was right. You half-expect a similar right-of-passage transformation to happen with your peer group — it’s unlikely.

Second, it’s not clear what this means for societies coexisting at a larger scale — I can’t speculate on that either.

And lastly, everyone probably harbors some secret, selfish hope that those who’ve wronged us might one day develop some future self-awareness and regret their clumsy missteps — oy, this rarely, rarely happens either. You have to keep doing the right thing just because it’s the right thing.

You already know that you aren’t self-aware. It makes you a little uncomfortable but boy, how you’d really like to join that 5%!

So the advice. I know you’re hoping for a top ten list with easily digestible bullets and actionable tidbits. But, actually, my single piece of advice to you is philosophical and just three words…

“Don’t be self-aware.”

I know this runs contrary to everything within you — your desire for truth, to do well by others, and for self-efficacy. However, when you are self-aware, you can’t dance without feeling ridiculous, talk without freezing mid-sentence, learn at any reasonable speed, or help but blame yourself for not getting along with everyone. The start-up pace is so relentless that if you commit yourself to self-awareness now, you will spend too many hours replaying events in your mind and crushing yourself under the weight of self-criticism. It’s hard to balance the humility of self-awareness with the confidence it takes to run a start-up. Self-awareness is a destination you need to know how to get to but it’s no place to linger.

It’s also refreshing to have people who are woefully un-self-aware in an organization — those are usually the folks who have a lot of perspective to offer, who don’t bow to an organization’s normalizing pressure, and who keep that spark alive. Your team will be a happier, stronger place if you postpone your quest for self-awareness, focus on just being comfortable with your own skin no matter what you learn about yourself, and keep Meebo a kind environment for everyone.

I know what you’re thinking, “Elaine, you came back all the way in time just to tell me this?!!!” Sigh… yes. And from one perfectionist to another, you know I wouldn’t do it without a ton of reflection and consideration. Perhaps your favorite quote will help:

“There are works which wait, and which one does not understand for a long time; the reason is that they bring answers to questions which have not yet been raised; for the question often arrives a terribly long time after the answer.” — Oscar Wilde

Love,
-Elaine

P.S. And spend more time with your future husband too!