Sometimes, life seems upside-down.

I originally wrote this post months ago, but I’ve been too self-conscious to publish it until now. This quote convinced me to put on my big girl pants:

“The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists on the inside, showing too much of yourself. That’s the moment you may be starting to get it right.” – Neil Gaiman University of the Arts Commencement Speech

So, here goes, and I hope it helps at least a few of you.

Reality Check

A few months ago, I had a birthday party.

A dozen friends and I gathered for several days of wonderful sun, beach, and catching up. On the last day, I didn’t get up until 11:30am, knowing full well that the last remaining friends were leaving at 12 noon.

I was afraid of being alone.

Like a child, I hid my head under the covers (literally) and hit snooze until reality couldn’t be postponed any further.

But…why am I telling you this?…

The Dangerous Myths of “Successful” People

We all like to appear “successful” (a nebulous term at best) and the media like to portray standouts as superheroes.

Sometimes, these dramatic stories of overcoming the odds are inspiring. More often, they lead to an unhealthy knee-jerk conclusion:

“Well… maybe they [entrepreneur/artist/creator painted as superhero] can do it, but I’m just a normal guy/girl…”

This post is intended to give a behind-the-scenes look at my own life. Though I’ve occasionally done profiles like A Day In The Life with Morgan Spurlock’s crew, I rarely let journalists follow me for a “normal” day. Why?

I’m no superhero. I’m not even a consistent “normal.”

In the last 3 months, I’ve:

Cried while watching Rudy.

Repeatedly hit Snooze for 1-3 HOURS past my planned wake time, because I simply didn’t want to face the day.

Considered giving everything away and moving to Montreal, Seville, or Iceland. Location varies based on what I’m escaping.

Seen a therapist for the first time, as I was convinced that I was doomed to life-long pessimism.

Used gentlemanly (ahem) websites to “relax” during the day when I clearly have urgent and important shit to do.

Taken my daily caffeine intake (read: self-medication) so high that my “resting” pulse was 120+ beats per minute. 8-10 cups of coffee per day minimum.

Worn the same pair of jeans for a week straight just to have a much-needed constant during weeks of chaos.

Seems pretty dysfunctional, right?

But, in the last 8 weeks, I’ve also:

Increased my passive income 20%+.

Bought my dream house.

Meditated twice per day for 20 minutes per session, without fail. This marks the first time I’ve been able to meditate consistently.

I’ve cut my caffeine intake to next-to-nothing (in the last 4 weeks): usually pu-erh tea in the morning and green tea in the afternoon. I’ve had no more than 1 cup of coffee per week. More on this in a later post.

With your help, raised $100,000+ for charity:water for my birthday. (Thanks to John Park for bringing the thunder!)

Raised $250,000 in 53 minutes for a start-up called Shyp.

Signed one of the most exciting business deals of my last 10 years.

Added roughy 20 pounds of muscle after learning the pain and joy of high-rep front squats (and topical DHEA, courtesy of Patrick Arnold).

Transformed my blood work.

Realized — once again — that manic-depressive symptoms are just part of entrepreneurship.

Come to feel closer to all my immediate family members.

The Point

Most “superheroes” are nothing of the sort. They’re weird, neurotic creatures who do big things DESPITE lots of self-defeating habits and self-talk.

Personally, I suck at efficiency (doing things quickly). Here’s my coping mechanism and 8-step process for maximizing efficacy (doing the right things):

1) Wake up at least 1 hour before you have to be at a computer screen. E-mail is the mind killer.

2) Make a cup of tea (I like pu-erh) and sit down with a pen/pencil and paper.

3) Write down the 3-5 things — and no more — that are making you most anxious or uncomfortable. They’re often things that have been punted from one day’s to-do list to the next, to the next, to the next, and so on. Most important usually = most uncomfortable, with some chance of rejection or conflict.

4) For each item, ask yourself:

– “If this were the only thing I accomplished today, would I be satisfied with my day?”

– “Will moving this forward make all the other to-do’s unimportant or easier to knock off later?”

5) Look only at the items you’ve answered “yes” to for at least one of these questions.

6) Block out at least 2-3 hours to focus on ONE of them for today. Let the rest of the urgent but less important stuff slide. It will still be there tomorrow.

7) TO BE CLEAR: Block out at least 2-3 HOURS to focus on ONE of them for today. This is ONE BLOCK OF TIME. Cobbling together 10 minutes here and there to add up to 120 minutes does not work.

8) If you get distracted or start procrastinating, don’t freak out and downward spiral; just gently come back to your ONE to-do.

Congratulations! That’s it.

This is the only way I can create big outcomes despite my never-ending impulse to procrastinate, nap, and otherwise fritter away my days with bullshit. If I have 10 important things to do in a day, it’s 100% certain nothing important will get done that day. On the other hand, I can usually handle 1 must-do item and block out my lesser behaviors for 2-3 hours a day.

It doesn’t take much to seem superhuman and appear “successful” to nearly everyone around you. In fact, you just need one rule: What you do is more important than how you do everything else, and doing something well does not make it important.

If you consistently feel the counterproductive need for volume and doing lots of stuff, put these on a Post-it note:

Being busy is a form of laziness–lazy thinking and indiscriminate action.

Being busy is most often used as a guise for avoiding the few critically important but uncomfortable actions.

And when — despite your best efforts — you feel like you’re losing at the game of life, remember: Even the best of the best feel this way sometimes. When I’m in the pit of despair, I recall what iconic writer Kurt Vonnegut said about his process: “When I write, I feel like an armless, legless man with a crayon in his mouth.”

Don’t overestimate the world and underestimate yourself. You are better than you think.

And you are not alone.

And If You Struggle…

If you occasionally struggle like me, these resources and articles might help you rebound:

The Prescription for Self-Doubt (Video)

Harnessing Entrepreneurial Manic-Depression: Making the Rollercoaster Work for You

Two Root Causes of My Recent Depression (by Brad Feld, one of my favorite start-up investors)

Did you find this post helpful? Please let me know, and if you have any particular strategies or quotes that help get you out of funks, please share in the comments!

Note from the editor: For more productivity advice, check out the following videos on YouTube from Tim:

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