When I was in the throes of entrepreneurship, running my struggling commercial printing company and my struggling tech company simultaneously, I had a vividly clear thought in my head.
I thought, “If I could pay someone a thousand dollars to just listen to me talk about my business problems, I would.”
And that, fundamentally, is why I am an executive coach today.
Starting off my career as an investment banker, then a corporate attorney, I felt very limited. As a banker, my life was all about standing by the fax machine (yep — I just dated myself), traveling, and managing spreadsheets. As an attorney, my life was all about reading, writing and billing.
I always felt like I had more to offer the world than just my liberal arts skills. I felt like I could recruit, sell, create a vision, craft strategy, build product, manage, code and more. I felt like I needed entrepreneurship to truly maximize all of my skills and really challenge myself.
And boy did I ever get that challenge. Entrepreneurship was by far the hardest challenge and most rewarding experience I’ve ever had in my career. I have been an entrepreneur now for more than 15 years.
Entrepreneurship can be thrilling, but also brutal. (So are other professions, of course, and I don’t mean to discount the challenge of other professions, but I am writing simply from my personal experience).
I was sole owner and CEO of my commercial printing company, where 1,000 things went wrong per day, and I was sole founder and CEO of my tech startup, where 1,000 other things went wrong per day.
Though I consider myself to generally be pretty level-headed and even-keeled, I was frequently on edge as an entrepreneur, and I often carried with me an enormous and unwanted baseline of stress.
Being an entrepreneur (especially without partners) is a hellaciously lonely existence. Nobody cares as much as you do, there is a line between you and your employees, and the stakes are very high. It is hard to find empathy, and it therefore makes for an extremely emotionally vulnerable position to be in. Even having co-founders and partners is no panacea. In many cases, having co-founders can even compound stress if founders are at odds with each other.
Entrepreneurs need a listening partner. I firmly believe they need a coach.
They need someone who is paid to simply sit there and hear them brag about their successes and cry about their failures. Entrepreneurs need to talk about all of their fears, their fear of failure, their fear of embarrassment, their concerns about their business, their investors, their employees, and frankly, the whole kitchen sink. They need to be able to speak with grandiosity, pride and even pain without fear of judgment.
They also need a sounding board. The echo chamber of one’s own head makes it impossible to have any perspective on what is really going well and what isn’t, what are the right moves to make and what aren’t. It is too hard to self-assess when you are the sole creator of your own business universe.
It is vital for mental health and peak performance to speak to someone you trust who is focused on hearing you. I believe this with all my heart.
And so, when I stepped off the entrepreneurship train after selling my company last year, I wanted to dedicate my time to helping other entrepreneurs who are on this warpath.
I feel particularly equipped to help others because I have been an entrepreneur twice for over a decade, and I have the financial and legal acumen to buttress my general advice with specific time-worn knowledge.
Furthermore, my personal qualities made me feel like being a coach would be a natural path. I love talking to people one-on-one, and I am most proud of my ability to understand and connect with people.
I didn’t actually seek out my first coaching engagement. A former student of my business class at General Assembly reached out to see if I would be interested in coaching him. During my class, he developed a startup idea, and shortly after, raised seed funding. I am forever indebted to him for being the first to trust me as a coach, and for lighting the pathway to my current career.
Taking my first few steps in the coaching world, I was afflicted with an initial and mild dose of impostor syndrome. Are coaches charlatans? Does anyone need them? Are they just a crutch and a dependency? Do I even know how to coach someone? Do I need credentials or training?
I have been coaching for nearly a year now, and I am happy to say that these questions don’t bother me anymore. I absolutely love coaching, and I have been relayed heaps of positive feedback by my amazing coachees.
One of my favorite pieces of feedback came from a wonderful founder who expressed in the most “millennial” way possible his appreciation. At the conclusion of our second session, he exclaimed, “Holy frick! This is soooo incredibly helpful!”
Holy frick, indeed. I love coaching, and this is how I got here.
I have a bad attitude about doing self-promotion.
I don’t mind, and in fact, I will even relish opportunities to talk about my accomplishments and my capabilities in a 1-on-1 or small group setting. But it’s the online self-promotion game where I really struggle.
In all of last year, for example, I made but 1 solitary Facebook post. (And it wasn’t even that good).
There’s something about the permanence of online communication and the 1-to-infinity distribution of content that makes me suddenly shy about sharing.
But in attending an evening talk recently about personal branding, I listened as a social media guru implored the audience members to “live a life curated.” She encouraged us to get with the program and to Facebook, Instagram, Tweet and Snap our way to relevance.
On the one hand, the point is well taken. In our post-Industrial economy, many individuals are no longer cogs in a very large machine, but are instead freelancers left to fend for their own careers. One’s personal brand and network becomes the only asset they can count on. Promote yourself or risk oblivion. Get a YouTube channel, start uploading, and don’t stop.
The Narcissism Economy (as I like to call it) is in full gear, and impresarios rule the roost (Kim Kardashian being an inarguable example).
On the other hand, you can only be you.
If social media isn’t your thing, it’s painful and mostly fruitless to fake it. Authenticity is still the gold standard, whether you choose to be digitally extroverted or introverted.
But like anything, I suggest making the best of what you’ve got. Personal branding and digital promotion are trending upwards, not downwards. For better or worse, we need to get on the train or risk being left behind.
From the vast buffet of social media choices, however, we are still free to pick and choose what we want to partake in.
I can’t seem to motivate myself to do anything on Instagram, but I have discovered that I enjoy blogging on Medium.
I feel very self-conscious recording videos of myself offering quick coaching tips, but I know it has helped some people, and I do get a kick out of learning the ins and outs of the technical A/V gadgetry.
Oftentimes, when we experience resistance, it is a sign that an opportunity for personal growth is right in front of us. We can tell ourselves our same old stories that rationalize why “the future is wrong” and “my view is right,” but there is an alternative.
That alternative is to say, “I will embrace something uncomfortable. This is outside of my wheelhouse, but I’ll give it a shot and accept that I might look like a dork.” It’s brave, it’s scary, and it may lead to some embarrassment, but it’s a step in the right direction.
So yeah, I really do hate self-promotion. Hang on while I click…
What percentage of your work day do you spend consuming things? How much time do you spend each day consuming Facebook, Instagram, Twitter, Snapchat, Hacker News, Techmeme, Google Finance, ESPN, Wikipedia, or whatever else suits your fancy? 30 minutes per work day? 1 hour per day? 6 hours per day?
I was speaking with an attorney friend recently, and I asked him how much time he wastes during the day, consuming sites like ESPN. I suggested possible answers.
“30 minutes per day?”
He replied, “Yeah, definitely. Or maybe more like 2 hours. Yeah, 2 hours, easily, on ESPN alone.”
This is symptomatic of the digital world we live in today. Everyone — blogs, marketers, journalists, friends, media outlets — is becoming a master at grabbing attention. The firehose of information flying in our direction is at an all-time high. And it will only increase.
In the old days, if you wanted to learn what camera you might want to buy, you could go to a store, ask a few questions and purchase it. Or you could ask a friend. But now, 9 trillion terabytes of YouTube reviews, web reviews and other purchasing options await your precious attention.
It can almost create a sense of digital nausea. How many words a day does the typical desk worker consume nowadays? How many photos and videos? I think it’s staggering, and I’m not sure our brains were evolved to handle this much verbal data consumption.
We all fall into this trap. Personally, I don’t consume the FITS (Facebook, Instagram, Twitter, Snapchat) much, but I definitely research everything to death and I love to follow my curiosity down so many intellectual rabbit holes, usually starting with a Hacker News post or a Wikipedia search.
In contrast to consumption, what percentage of your day do you spend creating things? Writing a blog post, shooting a video, penning a document, writing a book, using your hands to craft something? I would surmise that the typical desk worker consumes at least 90% of the day, and creates only 10% of the day, if not worse.
Imagine what would happen if you consumed no digital data at all during the day? What if you wandered into an actual forest armed only with a notebook and a pen. What would you create?
Seth Godin has said that some writers find efficacy in boring themselves to death so that they can write. Would Jack London or Ernest Hemingway have created their works of art if they were plugged into the 24-hour attention-splitting wonder-chine that is the internet? No chance.
There is a reason why Henry David Thoreau wrote Walden by a pond, not a modem. (Only took 40 seconds and 10 billion neurons to verify that on Wikipedia).
This is not meant to be an indictment or a judgment, just an observation. We are bombarded. Seriously bombarded. We are bombarded by information overload to the sickest degree.
The only solution, I think, is to take some time to shut off the firehose. Allow yourself to be bored, to be dumb. Not everything has to be looked up on the internet the second the question is posed in your head. Empty your mind.
If you are a startup founder, my firm belief is that you need a coach. Stat.
Why? Well, let me count the reasons… Being an entrepreneur is stressful, intensely so. When the going gets tough, as it inevitably does, to whom are you going to turn to express all your fears, hopes and frustrations? Your significant other? They can’t hear anymore. You will do nothing but inject fear and pessimism into the heart of the person whose support you most desire.
Speaking to an employee as a business confidante is another bad idea. Well-intentioned though you may both be, the CEO-level of transparency must stay beyond earshot of any employees, for reasons of conflict of interest and morale. You wouldn’t want the pilot of your plane to tell you that they’re secretly afraid you’re going to crash, would you?
Speaking to investors is admirable, but let’s be real, you’re human. It’s hard to be 100% honest with the person who’s entrusting you with their money and whose opinion you care deeply about. It’s just a completely normal human reaction to want to spin things for your investors, for the benefit of everyone’s morale.
Speaking to your friends becomes overbearing when all you talk about is your startup and your startup’s troubles. Either you are perceived to be blabbering on and on about first world problems or your friends’ recommendations aren’t what you’re looking for (you probably just want to vent and have no desire to hear any suggested solutions) or your friends really just don’t care to hear about all your crap, as they have enough to deal with themselves.
That’s why you need a coach — someone you pay to hear you talk about all your business crap. And there’s a lot of it. To steal a line from Thomas Hobbes, the life of a startup is nasty, brutish and short.
You need to be able to say the unsayable, you need to spit out articulations of your worst fears, you need to be able to express that you don’t know what the heck you’re doing, and you’re frustrated and scared. You need to be able to say your employees are incompetent and don’t care as much as you do.
You need to be able to say all of that and then throw it away. And then to recover and rebuild and get back to the business of kicking butt. And only someone you pay, who is outside of your company and outside of your social life, will listen to that and give you exactly what you need.
This may seem like the most self-serving post of all-time (I am a startup coach, after all), but I say it from the bottom of my heart with the deepest sincerity and a genuine concern for all entrepreneurs.
Talk to a coach. Stat.
This is not easy for me. In the blogging age that we now live in, sharing our thoughts and our lives on-line comes second nature for so many. Not so for me.
It has taken me months just to get from my first post on Medium (a one sentence post, mind you) to this, my second post! And both posts are strictly meta, talking about what I’m talking about!
But I guess these posts are good because they share with you my voice. And so, to encourage regular posts, I will try my best to post as soon as I write, bypassing second drafts or any real polish. That’s the only way I’ll gather any motivation to put finger to keyboard.
And I must remind myself not to age myself by refusing to dive into those popular activities of the young‘uns. I will out myself right here right now as someone who has never stayed in an AirBnb (no thanks!), never ridden an Uber or Lyft (gasp!) and who thinks Snapchat is for the birds. And no, I am not 120 years old.
But I digress (just aged myself again!). All I mean to say is that to not stretch oneself is to ossify, and I am definitely anti-ossification at this point.
And the other reality I must come to grips with is the fact that we live in an era of personal brand marketing, and I think it’s here to stay. With the internet, everyone has a microphone. And to not pick it up and use it is to be left behind to wither. I refuse to do that.
On this blog, I will articulate my musings on technology and Silicon Valley. I will also pontificate on topics I deem relevant to my coaching clients or anyone else seeking an executive coach.
I hope you like what you find here. Please follow me/subscribe/like or whatever the heck they call it (can’t believe I’m doing this). Wish me luck, and see you around!