Why You Need a Personal Board of Directors

How to ruthlessly edit the people in your life.

“You are the average of the five people you spend the most time with,” is one of those slap-you-in-the-face quotes that has you side-eyeing all the regulars in your life. Jim Rohn said those words, which Tony Robbins pounced on, and then Tim Ferriss had his way with. Oprah even paraphrased it. It’s kind of a great concept, right?

“Are you good for me? Really good for me?” you wonder about your inner circle, judgmentally sizing up all the people you’ve let into your life. Given the truism that you can’t choose your family (heavy sigh), and given that many of your friends and coworkers might not be top-of-the-line influences in your life at this moment (especially if you’ve chosen them out of convenience), it’s not too late to assemble a group that’ll at the very least keep you out of jail, and at best, help you reach unfathomable levels of success. Let’s call this motley crew your Personal Board of Directors.

The good news is that you might not need to systematically abandon all of the derelicts in your life in favor of people who will help you get to the top. Upon further reflection, some of these derelicts might, in fact, be loving and loyal, and at the very least have a shared history with you involving way too much Goldschläger, which will provide consistently amusing reminiscences in the years to come. No need to cut those cords – just maybe don’t ask for life-altering career advice or input on your new start-up’s business plan. Think of these people like the childhood toy you just can’t part with; you’d never throw it out, but you wouldn’t bring it to a key meeting with a VC firm, either.

Five Personas to Add to Your Personal Board of Directors (on the Road to the Top)

Before the list even starts, let’s be real about something. You might not be a prize yourself (how else can you explain all that time you spent hanging around with the very slackers and ne’er-do-well-ers you’re now trying to ditch?), and so you’ll want to manage your own expectations about whether these five important people will want to even be near you. No worries, though. Even a meeting once every few months can make a big difference in steering you towards the big time and inspiring you in the right way. Most people are charitable enough to spend time on the phone with you a few times a year, too, in case they don’t want to be seen out in public with you.

  1. Connect with a proven winner – someone who has done what you want to do, quite successfully. Pick his brain about what worked, what didn’t. Ask them what skills you need to keep growing and developing to get to their level of success. Ask her what she’d do differently if she could do it all over again (and hope she doesn’t say, “not take this meeting with you”). Ask him to take you under his wing. Ask her if she’d be okay with being a very part-time mentor to you. Always pay for the lunch/ dinner/ drink/ Slurpee to balance out all the taking you’re doing in the relationship. (Worried how you’ll find this proven winner? A little flattery goes a long way. Look up successful people who happen to be based in your area on LinkedIn, tell them you admire their career trajectory, and that you’d love to hear their story. Successful people eat that stuff up.)
  2. Find yourself a creative person. These people are special because their brains work in ways that you only wish yours could. They’ll see new and unique ways to tackle some of your many, many problems, and if you’re open to these ideas, you’ll actually get somewhere. Creative people can be found in traditionally creative roles (like at marketing, branding, design, architect firms, etc.), and can also be found looking cooler than average at cooler than average coffee shops. Ask for a creative person’s advice and keep an open mind.
  3. Get to know a money person. You might be planning a massive expenditure in your start-up and your new confidante might be the one you need in your life to burst your bubble. Someone has to be smart with a calculator when you’re contemplating going to grad school, taking a sabbatical from the job that’s burning you out, or deciding to get a mortgage on your barista salary. The money person will be your voice of reason when you want something and have no idea if 2 + 2 = 4. (Tip! Don’t pick a money person who is an unrelentingly conservative downer. They’ll never give you the green light you’re looking for when you want to take risks, which is always un-fun. Find someone who can accurately weigh the pro’s and con’s and help you understand just how big a risk your dream might be.)
  4. Get in tight with a Gen Z’er. This person will likely be appreciably younger than you, and that’s the point. (Millennials are now over the hill, all washed-up. You need someone fresh, with more energy and a way more modern perspective on the planet you’re cohabitating.) This 18- or 19-year-old is the one who is going to show you, with a singular eye-roll, whether your idea is half-baked or not. This youthful little bundle of inspiration might also remind you of what it was like to be at the starting point of adulthood when you were blissfully ignorant and far less cynical. Use that energy and not-wedded-to-the-past perspective to your advantage.
  5. Surround yourself with your missing puzzle piece. You know, a special person who can round out that gaping, dysfunctional part of you that’s missing, no matter what it is.
  • If you’re prone to confidence-lacking bouts of “Who am I, a colossal failure, to pull this off?” find yourself a cheerleader. This person, just to clarify, should not be a pom-pom-carrying high school girl. This person is unfailingly enthusiastic about you and your potential – perhaps a tad naïve to believe in you more than you do, but nevertheless, necessary. Positive encouragement can be a powerful driving force, especially if you’re surrounded by an inordinate number of pessimists in your life.
  • If you’re all full of good intentions yet never follow through with anything, ever, you need a drill sergeant who will seek sick pleasure in holding you accountable. Find the person in your life who is willing to show up at your door on a Monday morning at dawn with a baseball bat to “ask” why you didn’t submit your weekly plan on Sunday night via email like you said you were going to. Empower this person to do whatever it takes to get you to comply with what you said you wanted, like revising your resume by the 15th, completing your next quarterly budget by the 20th, writing that book before you turn 50. (Tip! Discuss rules of engagement in advance, like how you both feel about cruel and unusual punishment, etc.) But really… a strong accountability partner can make all the difference in helping you to execute your plans.
  • If you’re a big-picture thinker and get itchy when you start to think about how the files are going to get organized, find a detail-oriented thinker. Conversely, if you get giddy about the details and might miss the big stuff, like where all this is going, seek out a big-picture, strategic thinker. Bounce ideas off your opposite, learn about where you’re falling short, and either ignore what you hear or incorporate some of their yins to your yangs and actually get ahead.

So, how to assemble this Personal BOD, this Power Circle, this veritable crew of winners to help lift you onto the stage to accept your award or climb your corporate ladder or whatever it is you want? You might already have some of these people in your network, so take a close look at the people you already know. You might need to get creative and ask your network for introductions. You might need to muster up the nerve to cold call someone you admire – someone you’d be honored to have in your inner world of success – to ask for a bit of wisdom. You also might want to become the kind of person whom others would love to have in their personal BOD’s.

At any rate, you get to choose who you spend time with (unless you’re a parent and my understanding is that there aren’t a lot of options if you don’t like your kid), so why not spend it wisely, with people who are positive, smart, enriching influences in your life? And word to the wise: if people all of a sudden start ghosting you to spend time with people who host podcasts and make their own cheese and have shelves full of awards, it might be because they read this, reevaluated their social sphere, and realized you didn’t make the cut. Assemble a better Personal BOD of your own and you’ll be in demand for others’ inner circles in no time.

Jodi Wellman

Jodi is a co-founder of Happy Work Spectacular Life, loves red Skittles (maybe too much) and finally got a Happy Spectacular logo tattoo.

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