11 Bits of Advice I Would Tell My 21 Year Old Self

Costa Rica, 1996

Today is my 41st Birthday. And while some people think I still live like I’m in college, I’ve actually learned a few things in my first two decades of adulthood. Here is some advice I wish I got at 21 — or at 31. Or even yesterday, because it’s a daily practice to remember this stuff.

Dear Edward,

1. The Best Places Aren’t In the Guidebook. There are those moments when life asks you to say YES to the unknown. Some of my most wonderful memories of traveling around the globe began with a simple decision — should I be open to the unknown or not? When we try to plan everything out, we preclude the limitless possibilities. Like the time a couple guys I’d just met and I trusted a Costa Rican fisherman to take us an hour up the coast to a “playa bonita” he said he knew. We ended up having a mile-long stretch of virgin beach and one of the sweetest little surf breaks in the world all to ourselves for the better part of a week. All because we trusted in the unknown.
2. Get Reality Checks from Those Who See Your Highest Self. Years ago I took a job as an international political consultant. I traveled the globe making more money than I ever thought possible providing campaign strategy advice to presidential candidates of foreign nations. The money and power went to my head, and I started to treat people poorly. It took my best friend from college sitting me down and telling me I was “turning into a total DB” before I saw what was happening to me. Your best friends know the best you. Listen to them.
3. Wear Well Made Shoes and Suits That Fit. Ok, this might seem superficial, especially after #2, but bear with me. Like many young men, I went through a phase of wearing XL everything — in spite of weighing 165 lbs. This lasted until my late 20’s when I bought my first tailored suit and real leather shoes. The difference in how I felt and how people regarded me was not subtle. It was like putting on 10 years of stature and prestige. So, don’t waste money on cheap suits and shoes. You’ll just look…cheap. Instead, get 2 impeccable suits (1 navy blue, 1 dark gray/charcoal) and two pairs of Italian or English shoes (1 brown, 1 black), and wear the hell out of them. ProTip: Wear the brown shoes with the blue suit, and the black shoes with the gray suit, for god’s sake.
4. Cancel Meetings You’re Not Ready For. In one sense, we’re never truly “ready” for any meeting. We all need to take risks and just go for it. This isn’t about those meetings. This is about those meetings you really shouldn’t be having because too much is at stake and you might totally blow it. When I was 25 I had an important meeting with a member of Congress at 8am on a Friday. Unfortunately, Thursday night got away from a colleague and me, and I showed up to the meeting in no condition to be speaking to anyone. If you are going to lose more ground by having the meeting than by canceling, just cancel.
5. Talk to the Pretty Girl. Or the handsome boy. Or the VC you want to raise money from. Or the TV personality you always admired. I wasted years of my life not talking to the people I really wanted to get to know. I told myself stories in my head that they’d never want to talk to me. That I wasn’t cool enough, handsome enough, funny enough, smart enough. And then I realized that all those people were thinking the same thing about themselves. So, I started being more proactive. I talked to the pretty girl at the party. I told the TV personality I admired him and wanted to work for him. And sure, sometimes I got turned down, but most often, I got exactly what I was looking for — a date, a job, etc. Because life is sending you perfect pitches all the time. All you have to do is swing the bat.
6. Ignore the Haters. Sadly, there will always be people who don’t love themselves enough to love you. There will always people who see how you choose to live, where you travel, or what you’ve done and feel competitive with you. Heck, there are even those who imagine what you’ve done and who you are, and hate you for the image of you they have. Ignore them. All of them.
7. Copy People You Admire. When I was 26, I was doing research on the new motorcycle I had purchased, and I read about a couple traveling around the world on their honeymoon on my exact model of bike. I was so inspired, I decided to do a similar trip. Within 6 months, I had quit my job running an environmental non-profit and drove south. The travel blog I wrote about my trip ended up in Forbes and the Guardian, and inspired thousands more people to do a similar trip. Of course, there’s also the other side of the coin — don’t emulate people you don’t admire. Sometimes people seem like they have it all — like they should be good examples to follow. They have the wealth and influence you want, and a lot of other people try to emulate them. But something about them doesn’t feel right to you. Maybe it’s their business ethics. Maybe it’s how they treat women or their families. Just trust your gut and stay away from them. Far away.
8. If You Lead (Well), They Will Follow. I’ve learned that there are those people who demand respect, and those who command it. Demanding respect is leading poorly. It’s driven by self interest and fear of being judged or undermined. Commanding respect is leading through action and example. It is humble and is driven by a higher purpose. While leading well may also be nerve wracking, the fear that comes up is worry that others might not be well served by your leadership, not that your image might be tarnished. Just remember that in 99% of situations, people are looking for leadership. They are looking for selfless leaders. Give them the leadership they seek — in the interest of serving their interests — and they will follow.
9. Figure Out Your Unfair Advantage. We all have something we are naturally amazing at. Some people pick up the guitar or a paint brush and make art from the first try. Others can put into simple prose the huge ideas we can’t seem to get out of our heads. And still others can negotiate a business deal so well everyone feels like they need a cigarette once it’s over. Whatever you do so well that few others can match you, do more of it. My skill-set is two fold — 1) I help people get honest with themselves and put words, intention, and action behind their dreams, and 2) I can create a vision and motivate teams to bring great things to life. So, today, I’m both a coach and an entrepreneur. But I didn’t know that for a long time. I tried being a number of other careers before this one. And I have no regrets. All of those experiences simply made me even better at what I do today.
10. Choose Friends Who Dream Big, But Don’t Compete with Them. Friends who make big plans for themselves will push you to make big plans for yourself. Spend more time with those people. On the other hand, friends who think small will discourage your big dreams because frankly, no one likes being left behind. Spend less time with those people. But don’t EVER compare where you are today to where other people are. We all have our own timeline. We all have our own luck. Admire the success of your friends. Emulate it if you can. But don’t be jealous of it. Jealousy is the fastest way to lose the people you want to be closest to.
11. Build Your Dreams, or Someone Else Will Pay You to Build Theirs. Those people whom you admire most, the ones who have built companies, won elected office, recorded hit songs, etc… They didn’t get there by working for someone else. Sure, we all serve someone, whether it be customers, constituencies, or fans, but at the end of the day, you won’t leave the impact you want in this world by punching the clock for someone else. So, take the time you need working for mentors to learn your trade, but some time before you feel fully ready, set out on your own. Start a new firm. Launch a new start-up. Record a solo album. Just do it. And when you fail — which you will the first time or two — just get up and do it again. Because as they say, “Success is going from failure to failure without losing your enthusiasm.”

Love ya, kid.

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Edward Sullivan is the founder and head coach at LeadWell.co — a boutique coaching and training organization that helps start-up CEOs and corporate executives navigate the challenges of leadership with authenticity. With offices in San Francisco and New York, LeadWell helps leaders and their teams optimize their performance and overcome obstacles to growth. He can be reached at edward@leadwell.co.