As a kid, I was the guy everybody would call for advice. I would give the advice but always feel pressurized while on the call. I would think “Why the heck are all these people calling me? What do I know”? People thought I had lived a million years and done several things so I ought to have the experience and capacity to help them out in their situation.
Sure, I worked in MIT, had a business reproducing frescos, played in a band and toured around. So when I got these frantic calls from people, I knew I couldn’t fail. I had to help this person seeking my help otherwise I will let them down. It wasn’t so much the pressure of impressing – it was more about not letting people down.
To me, fear was letting people down ─ hearing people who had high hopes in me say “ I expected better from you.” was like a dagger. Disappointing people has always been a central fear of mine, and part of overcoming that fear was learning how to fail fast. To learn how to figure out if something is a bad idea or if I’m on the wrong path very quickly.
Personally, I’ve been able to pinpoint a bad direction by being really transparent. Each year, I write end-of-year blog posts that feature my top five to ten mistakes – or how I screwed up completely. Even today, these are the most popular, high-traffic posts on my blog.
When you’re transparent, you let your guard down and people can now relate to you. They appreciate both the good and bad stuff you did just because you’re not afraid to accept them as yours. Part of this means I’m also not your regular “Yes-man.” I am there to be direct in my business and agency. I represent authenticity and transparency when I’m at work. In a business, you can’t dance around an issue for billable hours. You must get your point across, decide the best course and get it done.
The Only Option is to be Yourself
One of the things I realized early on was this: I cannot be someone else when I show up in work and life. I can’t not be me. If I do, it’s not only doing a disservice to me, but also to the other person I’m trying to impress based on a false notion. When I used to work at Tutor.com, there was a guy named Ross who is still there as their CTO now. He was a great guy, a programmer, a hippie kid in those days. Once, we were stuck on an issue and Ross said, “You know, you’ll have to pull a Ferrin again.” (My last name at the time was Ferrin – I’ve since changed it to Alexander which is my middle name.) I asked him, “What do you mean”? And he said, “Man, you’re like the most fearless person I know about pointing out the elephant in the room.”
I can’t lie to clients when the elephant is clearly in the room! That’s fooling each other and I’d rather speak to people honestly and get it out of the way, “Here’s the problem, this is what I think we should do.”
I learnt the lesson of how to be me the hard way. For me, it was both personal and career-related stories that taught me how I had be myself. I was dating a girl when I was 26 years old and we were together for seven years or so. She was a great girl and we really liked each other– but she expected me to be someone I was not. I am not judging her for that. It wasn’t anyone’s fault, but I knew I couldn’t be who I wanted to be in order to give her what she wanted. For example, her mother was a wealthy CIA worker and wanted that package for her daughter too: a husband who could buy her a big house with a white picket fence – and that wasn’t me. So we eventually, we had to go our separate ways.
Another example is I used to work with two incredibly genius men on a business reproducing frescoes. They had a 3D printer on which I worked. I lived in Rhode Island at that time and commuted to Cambridge for work so it was five hours of travel a day for two and a half years. These two men were smart and they knew who they were. One of them, Jim, came in one day with a shaved head and started to shave his head regularly. After a few days, he suddenly stopped. He’d have this huge patch of hair and wouldn’t care much. I’d ask him, “Jim, what happened to the hair?” and he’d quickly reply, “Forget about that. Here’s what we should do.” He was one of the inventors of the machine we used twenty years ago, when this technology was pretty new. He’d appear quirky to an outsider, but if you stayed with him for a while, you realized this is just who he was – and he wasn’t afraid to embrace it! These men were hugely successful with their business. Just being with them energized me and helped me understand how important it is to be authentic.
How Do You Play the Game of Life?
Life is a chess game, with the goal to keep passing to wherever we want to pass. But in between these moments, there are moves. You have to make a move in order to reach somewhere on the chess board. As they say, the destination is not as important as the journey itself. To me, this means the moves are more interesting and mean a lot more than where I eventually reach. At every move, you have a choice which only you can and must make.
In 2009, we realized that a client at our agency was taking up an immense amount of our bandwidth and was bombarding us with requests. They were our client for three years in a row and we had hit a point where we needed new clients and new projects. It happens a lot in the agency world. But the problem was that 40% of our business was coming from this one client. Britta, my business and life partner, said we have to make a decision to let them go. We were fully aware that this would, at least temporarily, bring our income down to 60% of what we were making then. We’d have to make some tough decisions and let a few of our staff go. We’d have to develop new strategies to bring in new clients. Those were micro moves for us. The macro move was to get out of the deliverables business and focus only on providing services. And it was super scary and hard, but we did it! Basically, we had to go back to a defensive strategy versus an offensive strategy just like in the chess world.
So the big thing I realized was this: The game isn’t over if you lose your best players. The game isn’t over if you have to give up some clients. If your office burns down tomorrow, you can still be in the game and play. Make a move – and you’ll always pull it off. You just have to realize that the game of chess will go on; it’s not going to end. And know that you’re going to make it through whatever comes. It’s okay if you don’t know your next move – have the spirit to keep going!
Don’t Run to the Train!
And unlike the game of chess, life doesn’t have a timer. No one’s going to come and tell you, “Okay, you have 30 seconds to make your next move.”
You don’t have to be constrained by time. But in the real world we make time such a huge constraint. I understand deadlines and urgencies, but if you think about it, isn’t it all made up? How did we decide that a day will have 24 hours and not 25? It’s the fake constraints we’ve created to apparently simplify our lives. I have a principle in my life: I will never run to the train. If I run to the train, I don’t learn anything. I’ve invented a quick fix. Whereas if I let it go and take a breath, I’ve missed the train and am probably late for an appointment. What does that teach me? That I’ve got to leave earlier for my appointments.
The “Be Present” philosophy clicks. If you can constantly pull off not running for the train, then you’ll find the train is a decent analogy for life itself. You will not be jumping from things to things. Multi-tasking is the big bug of the 21st century. You’re doing five things at one time – checking emails, talking on the phone, watching a video online and so on. Instead of that, let’s just make most of this moment by focusing on one thing rather than squeezing multiple instances into it.
We can only deal with a certain amount of things at one time. So let’s just give into it and say, “I’m here. I’m at this appointment now. That’s where I am. I’m going to kick my feet up. Let’s have fun. Let’s be in this moment.” This practice, in and of itself, is something that’s legitimately helped me reduce a lot of panic and fear.
About: Ian is founder of EAT Media and has 20 + years of startup + creative experience solving content issues across digital and print mediums. He’s spoken on the subject of content strategy (and hip-hop) at SXSW, the IA Summit, and the Custom Content Council. He lives and works in New York.