/ uncomfortable

The Most Important Actions Are Never Comfortable.


January 16, 2013 the conference is over so I decide that betting the farm on a few games of Roulette at Harrahs is a good idea. Time flies in the Casino and all of a sudden we’re rushing to catch the 11:30 Red Eye from McCarren International. One four and a half hour flight and three timezones later, I’m stuck in a two-hour layover at Hartsfield-Jackson. A quick scare for leaving the keys in Las Vegas, before finally arriving home in sunny Charleston, South Carolina.

I was in Vegas for the Affiliate Summit West, the premiere affiliate marketing conference bringing together the biggest networks, affiliates and merchants in the world.  I have had some success in the past with affiliate marketing of prepaid debit cards, web hosting and few other products, so I thought going in that I would be able to hold my own.

The assumption was like living in a Manti Te’o fantasy world. It has been a few years since I’ve attended a tradeshow, but as I found myself surrounded by internet millionaires with their fancy matching Adidas track jackets, talking big money deals and me not knowing anyone… I couldn’t help but feeling uncomfortable and a bit overwhelmed.

Fight or flight, I’m going to choose fight.

When I first saw the early UFC’s of Royce Gracie choking out guys two times his size, I thought that I needed to learn how to do that. So I convinced my mom to let me sign up at Ground Control in Baltimore and drove into the city from the suburbs four times a week by myself.

As a scrawny teenager from the suburbs, learning Brazilian Jiu-Jitsu downtown without knowing anyone was initially somewhat terrifying. Far from being a natural talent, I struggled every single day. I kept going back each week and that experience along with bjj have both stuck with me forever.

**When is the last time you’ve felt overwhelmed? **

I’m not interested in a time that you thought there was too much to do or that you’ll never finish the paper you procrastinated on for the past ten weeks, but a moment that you signed up for and when it arrived you were like holy shit. Where you had to swallow that lump on your throat and go to battle?

If you can’t remember or something doesn’t quickly flash to mind, get out in the world and pursue something that you want to do. Sign up for karate classes, host a charity dinner or run a marathon. Push yourself.

You might be out in the world trying things, but if you’re not feeling overwhelmed or questioning whether you made the right decision then you’re not pushing it enough.

I question my strategies, business practice and blog posts all of the time. Am I doing this right? Is there too much risk? Should I be using my time better? I think that all entrepreneurs question themselves and change their minds regularly.

Jason Fried talks about his conversation with Jeff Bezos.

During one of his answers, he shared an enlightened observation about people who are “right a lot”.

He said people who were right a lot of the time were people who often changed their minds. He doesn’t think consistency of thought is a particularly positive trait. It’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicted your idea today.

I interpret this to mean people are often when right a lot because they change their mind based on experience. It’s why business plans are so largely invalid now. Technology and the marketplace evolve at such a rate that if you’re unprepared to change your mind or pivot to new things (The Lean Startup methodology), you will be doomed to failure.

Take the first step by moving outside of your comfort zone

We’re social people, but even the most talkative outgoing person can get shy in different situations. Stepping into a conference filled with unknown faces, networking at social events, talking to members of the opposite sex or starting a new job are all stressful because they’re outside of familiarity and can be uncomfortable. Largely people fear public speaking more than death… it’s time for you to test fate a bit 😉

I’m re-reading the 4 Hour Work Week now and Tim Ferriss emphasizes that,

The most important actions are never comfortable.

I’d love to print that quote out and stick it on my wall. Comfortable, easy, whatever… we don’t truly receive any value from something unless it’s challenging.

Applying this to your business.

Your friend starts a business, posts about it every day on their facebook page and then bugs you with a copy and pasted message to go like it. Likes are cool, but how many of these people are converting into paying customers? Probably none. This is similar to what I like to call the “Display Advertising Myth”, the notion that you can set up a website (without incredible copywriting and design) and pay for ads on Facebook or Google to gain new customers. As members of generation-y, we’re constantly barraged by millions of advertisements that we’re practically immune to it.

So quit being so comfortable and start picking up the phone and cold calling potential clients, distributors or decision makers. Draft email pitches designed to generate sales, start sweet talking a blogger or journalist to cover a news story, get out and go to conferences that make you feel like an idiot because you don’t know crap.

I’ve learned that it’s usually only when we step outside of our current network or social circle that we reach our target audience. As entrepreneurs we have to constantly move outside of the comfort zone to try test new models, hypothesis and never stop learning. It’s fun wasting time on Facebook (I do it all of the time but recommend using stay focsd), but won’t move the ball forward.

When your customer is calling up cursing worse than Samuel L Jackson in Django Unchained, pick the phone up with a smile and diffuse the situation without any gunfire. Getting into this mindset of always taking on new challenges and ending the avoidance of things that you hate doing, will take your business to the next level.

I remember when Kwame finally said that he’s not taking customer service calls anymore. It was a year and a half after founding GiftCardRescue and we were a multi-million dollar company. Yeah at some point you’re going to earn the right to outsource certain tasks, but largely this comes after the model is proven and business is growing. Not during the startup phase.

As your business scales and moves through the different phases, you too will move from doing one task that’s uncomfortable to the next. But the experience and knowledge will transfer over. You’ll be smarter, more agile and eager to try new things. Eventually it’s not about comfort anymore, rather you can’t imagine doing something where you’re not taking on a daunting challenge. And that is what living is about.

Note: I’ve generated a lot of interest for the master course on internet marketing I’m launching February 1. If you want to join the first group (limited to five people), you can fill out this survey.

Photo credit: ORRANGE. / Foter.com / CC BY-NC-SA


I make money online through websites and business consulting. Everyday I'm challenging myself to learn and do more.

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