The Best Advice, from your Best Friends
Because they know you better than you know you
When I look back at my life I can pinpoint a handful of really big decisions that would have sent me down very different paths. In each case, I relied on the advice of close friends. Sometimes I took their advice, other times I didn’t, but in each case their guidance was incredibly helpful in my process of making a call.
This photo above is from a party in Athens, Georgia in 1993—a time long before smartphones or social media, when people rarely brought cameras to parties. I just finished my junior year of college and a close family friend, Melissa, set me up on a blind date with the lovely young lady on the left, Stephanie. While blind dates usually fail, I went into this one thinking it might be a great match, since Melissa knew both of us so well. We hit it off, spent much of that summer together, and this week we will celebrate both our 25th anniversary and the high school graduation of our second daughter.
Steph is my best friend, and in our journey together there have been very specific occasions where she stopped me in my tracks as I wrestled with a tough decision and/or emotional struggle, pulled me out of despair, and showed me the right path. Sometimes her advice is tough, but it comes not from “Here’s what I would do” but rather, “I know you well, and this is probably what will make you happy.” And it’s usually followed with, “Do what you wish and I will be supportive no matter what.” Taking her guidance has resulted in any success I can claim, and I have modeled her approach to be a better friend to others in return.
In a world where we tend to “connect” with thousands of people, I hope this post is a reminder of the best of friendship.
Why Your Best Friends Know Best
Research suggests that a big chunk of our brains evolved to maintain models of the people we cooperate with. And the closer someone is to you, the more accurate that model is. Your best friends know you extremely well—your good, bad, and ugly. But they are not literally in our brains, so they can bring useful advice without the cloud of emotions that often hurt our decision making.
At my last startup, company struggles and senior team drama came to a head. I had doubts about my ability to step up and succeed in taking over the CEO role. I was very close to just packing up and quitting. Being a company founder is lonely and the stress was the highest I’d ever experienced. I decided to share my struggles with two good friends, Jeff and Eric, who knew me and the situation very well. They built my confidence up and motivated me with some verbal kicks in the ass. As a result, I fought for the opportunity, we turned around the company, and I realized that this role is my true calling.
This example points toward the second big reason your best friends’ advice can be valuable: They still have to be around you. Lots of people are happy to give you advice, but many of them barely know you or your specific situation. So the advice is mainly, “Here’s what I would do” when what you’re often looking for is “I know you and this is what I predict will make you happy.”
In my startup, Jeff and Eric were directly connected to our company and had a stake in our outcome. I don’t believe they would have encouraged me if they didn’t think I could do the job. Within my family, Steph has a big stake in the business decisions I make. She’s not specialized in startup financing, but she knows my strengths and weaknesses, and her checks and balances of them have been a secret weapon in negotiating my equity and exits. No matter what the situation, it’s in your friends’ direct interests for you to be happy.
How Seek and Process Advice
Long ago I took a lesson from Socrates: “He who is wise admits he knows nothing.” It is a powerful habit to pause before you make a big decision and get some outside perspective. For me, it comes from a realization that I’m too close to something and I’m more afraid of my biases driving bad decisions than feeling embarrassed to ask for advice.
When you ask for feedback or advice, you must be truly open to it. You should not seek to “validate” a decision that you’ve already made. Do not think of sharing with friends as checking a box or seeking their approval in advance. Choose to be open and truly listen. Even if you end up disagreeing, you will be more confident in your decision.
Diversity of perspective is critical too, as just relying on a handful of close friends might not be helpful in areas outside of their experience or knowledge base. That’s why I also believe in purposely curating friendships in a wider circle. This is friendship, not networking, which also has its place, of course.
For me, elevating from network acquaintance to friendship tends to come from when I meet someone and kind of “hit it off.” We tend to overlap in business or industries, of course, but these real friendships tend to be sparked by some hobby or other personal interest. Those common interests bring you together and make it easier to pick up a conversation even if you haven’t spoken in years. When you need some outside perspective, they are there and ready to help.
And if you don’t have a friend to speak to at the moment, there’s even a way you can get their help by stepping outside of your mind and into their shoes. Simply ask yourself what a good friend would advise you to do if in your situation. This reframing alone can often snap you out of your struggles and clarify the best way forward.
The longer I live, the more I believe that “I” is really “Us”. In so many ways this is the inspiration for building our startup, Hearty. We are products of the people we are around, from family to school to work and more. We’re constantly in each others’ heads, sharing information, and counting on each other to accomplish anything. Seek relationships with people who make you better, and pay the world forward by offering encouragement and advice to other comrades you meet along the journey. Be the friend you hope to have.