This blog post has been a long time coming. In one sense, it’s taken me the better part of 2018 to organize my thoughts on the topic and actually, y’know, write this blog post. In another sense, writing this post has taken my whole life.
If you’ve come seeking practical technical marketing advice, begone! You’ll find none here. But if you’re interested in learning how one introverted Type B internet geek has been able to helm a successful company, read on!
I never wanted to be the CEO of a company. I was certainly not someone who, as a teenager, fantasized about starting a business and making a million dollars (that was a lot of money at one point!), but I definitely had friends who couldn’t wait to get started in Business and make their first million. In my late teens and early 20s, I had no interest in attending business school; in fact, I was a working toward a classical music major for most of my college career, which is just about the antithesis of a business school degree (AKA the “Let’s go have an actual career making money” degree).
But despite all that — despite never wanting to be a CEO, a business person, a corporate stiff — I always wanted to be a “leader”. As a nerdy and gangly 7-year-old kid growing up in the suburbs of Southern California, I didn’t have a lot of friends. Accordingly, I really valued the friends that I did manage to pick up. We were a tight-knit group of misfits (not in the cool punk rock way, just the way in which no one is picking you for either sports teams or group class projects). Throughout elementary school, we’d find ourselves playing pretend and building forts in the hills of Conejo Valley. At one point we decided that we needed roles and structure, a la Teenage Mutant Ninja Turtles, G.I. Joe, or the Planeteers. So we came up with unique roles for ourselves and we even gave our ragtag team a name. It’s embarrassing. Some things are better off (not provided).
The team role that I desperately wanted for myself stood in glaring contrast to my personality.
I wanted to be “The Leader”. Like Leonardo from TNMT or Duke from G.I. Joe. I wanted this, badly, despite being painfully shy and quiet. My one and only simultaneous skill and defense mechanism was to run really fast (usually away from things). But nonetheless, I always wanted to be The Leader.
Hi, Little Mike. Welcome to the real world. Being a leader = not a position you’re suited for. Sorry, kid. — Life
Oh, okay. That’s all right I guess. — Young Me
That was the extent of my leadership aspirations for the majority of my young life. It didn’t seriously come up again until I got into my 30s.
Now I’m not faulting any particular group, making excuses, or even saying that “this is how the world is”, but the fact is that from my vantage point as a kid growing into a teen and then growing into an adult, I kept getting a pretty clear message over and over again: in this world, the leaders are confident and aggressive. They can talk to anyone and sell a glass of water to a drowning person. They command the attention of everyone in a room and give orders with authority and hold people accountable. They yell sometimes. As I entered the workforce, those points were hammered home, and the traits I thought a leader needed were exemplified by my bosses.
The only people who I saw running “successful” companies (a word which, I now realize, is very open to interpretation) were stern, if not iron-fisted, managers. They made the rules and set the goals with confidence. They weren’t afraid to yell to get their point across, and they’d make hard calls about firing and downsizing without looking back. They got to say “do as I say, not as I do” (many were quite fond of that one). What’s more, they could sell like nobody’s business without (seemingly) even trying. Let me be clear, I’m not taking a passive-aggressive shot at my former bosses here. These are just the qualities and traits that, based on my experiences, seemed to correlate strongly with success in leadership.
Even as a team manager and then director at my last job (i.e. where I was an employee), my bosses — the people who actually had skin in the game — we’re completely unlike me. Even though I was in “leadership”, I was firmly convinced I could never be The Leader.
So what the heck happened? What changed?
Almost four years ago, I was terrified to start this journey. Founding UpBuild meant I had to be the Leader of something serious, regardless of whether I felt ready or qualified. I had to be the Leader despite all my bosses thus far implicitly showing me that I didn’t have what it took (one explicitly told me once; thanks for that). I was not a Type A Extrovert. I didn’t exude confidence. I couldn’t sell. But I was going to do it anyway, and I think it’s gone pretty darn well.
In the rest of this post, I want to share some of what I’ve learned about being the CEO of a company as an intensely introverted Type B geek. I’m afraid I don’t have the How To field guide yet and it’s possible that I never will. For anyone reading this who finds themselves in a similar position, I hope this can be of some help.
Obstacles & Challenges
Shy, Scared, and Easily Exhausted
It’s a common misconception that introverts are shy by default. There are plenty of folks who are outgoing and talkative but who regain their energy by being alone. I am not one of those. I’m both extremely shy and intensely introverted. In fact, I still get incredibly nervous before every phone call and meeting and afterward, I’m exhausted. That’s a core challenge and perhaps the one from which most other challenges stem.
Being Type B in Pursuit of Type A Success
The Type A & Type B Personality Theory holds that Type B people are less driven but are still motivated to succeed. However, they are more likely to enjoy steadily working toward achievement and will more easily draw fulfillment simply from the process of getting there. They are compelled to explore ideas and concepts in-depth and, by comparison to Type As, are less competitive.
That’s very much how I identify, and so it’s been a challenge to reconcile that with the fact that success in business typically goes to either Type A individuals or Type A organizations. After all, “fortune favors the bold,” and the victor is likely to be the most ambitious, driven, and proactive. Not to mention that in Silicon Valley/startup culture, it’s the charismatic Type A powerhouses that most often earn the write-ups and interviews. That’s not to say this is always the case (it’s not) but it’s a pervasive idea that I found that I had absorbed much more than I would have liked.
Hacks & Alternative Paths to Make It Work
What to do when the cards seem stacked against you? The answer (for me at least) was not to simply try to become Type A and succeed using that playbook. It was to find workarounds and figure out what I could do to make things easier for myself.
Play the Role
This might sound kind of funny, but I often think of certain leadership activities like acting. When I need to talk to a client or make a big company presentation, I don’t necessarily feel like I’m in my element. What helps me is to act according to this role I’ve built out in my head. It’s hard to describe but it’s an idealized reimagining of the extroverted leaders I’m so familiar with. It’s a bit about taking the strengths that I’d like to see in myself and modifying them to fit what I can embody, then playing off that in key moments.
This might not have much to do with Type B introversion, to be honest, but I’ve learned to use preparation to make leadership easier. I take a long time to think over decisions, come up with graspable ideas I want to convey, and figure out how to say it. So knowing that, I bake in time throughout my day to prepare in that way. I often write out long pseudo essays to myself in which I’ll convince myself to change something I’m thinking about, possibly change it back, and finally arrive at the decision I want to go with. Another way that I prepare: meditation. Meditation has been an incredible tool that I use before big calls, meetings, conferences, etc. I can’t imagine doing any of this without a meditation practice.
Start a Distributed Company
I honestly have no idea if I would be able to successfully lead UpBuild if we were a company with a brick-and-mortar office with face-to-face meetings each day. I probably would have burned out in the first six months, I wouldn’t have been able to convince any clients to work with us, and the team would have lost all faith in me. I’m being dead serious when I say that the asynchronous nature and disconnection inherent to remote work (i.e., almost always being on the other side of written emails instead of face-to-face conversations) is the only reason anyone thinks I know what I’m doing. The most frequent tool I use is stepping away from my desk for 5 minutes and fine-tuning email drafts. Being at the head of a remote company and working with clients over email allows me to come across as very articulate and insightful; I don’t think I would come across as either of those things in a traditional office, but who knows.
Batch Meetings & Calls
Ruth and I like to joke about this, but at UpBuild, Tuesdays and Thursdays are simply “Meeting Days”. To expect to get anything else done is a fool’s errand. The good thing is that meetings are work, too, they’re just a different kind of work. Being an introvert who can easily feel drained after interacting with people, I’ve found it best to batch as many calls together as possible.
Let’s consider a hypothetical but pretty average day. I have 7 meetings that I’m committed to. There are 5 30-minute meetings, 1 45-minute one, and 1 60-minute one. I can either let those land wherever or try to batch them and put them into tight blocks. Why does that matter?
As an introvert, I lose energy through interacting and gain energy by not interacting. Based on what I’ve experienced over the course of my life, I’ve found the following to be more or less true at work.
Imagine I have 100 Energy Points that keep me going. I might start the day with 100 points and as I go about my day, I’ll start to feel pretty drained and unproductive once I’m below 50. To make matters more challenging, if I haven’t slept well or if I’m stressed out about other things, I might not even start the workday at 100 Energy Points!
Each interaction (usually a call or meeting) requires 10 Energy Points. It’s interacting and, as such, drains me a bit. On the bright side, I’ve learned that if I have a few meetings back-to-back, each successive meeting takes about half as much energy out of me as the one preceding it because I’m still in social/interaction mode. Three consecutive meetings is a lot easier to deal with than three spaced out meetings where I get out of “interacting mode” but don’t have the chance to recharge in a meaningful way.
Conversely, I can regain energy throughout the day, but it takes longer to refill than it does to spend. I’m telling you, the game mechanics here do not necessarily maximize fun. Nonetheless, if I can have about 90 minutes without significant interaction (Slack messaging and email don’t have the same impact) I can regain 5 Energy Points. If I can add another 60 minutes on top of that, I can get another 5 back. I rarely get to do this, but I’ve also found that if I can get a 25-minute nap in, that’s an easy 10 Energy Points back in the tank.
To see what I mean, check out the timeline and chart below for a day without batching (orange) compared to a day with batching (blue). Without batching has me end my day with 45 energy points; with batching leaves me with 85 and I’m stoked to come back to work the next day!
And here’s the full (completely non-scientific) dataset.
Embrace Who You Are & Trust Your Motivation
This might seem like pretty fuzzy advice, but it’s a big takeaway for me. I think that the make-or-break quality of a successful startup founder or CEO is having intrinsic motivation for doing what you’re doing. External motivation is easy to come by and can just as easily vanish or just be forgotten. Building something to make money, seize a market opportunity, or earn recognition is fine and can get you by for a time, but when times get tough and the road ahead isn’t clear you need to be able to rely on your own internal motivation to get you through. If you have a reason, deep in your bones, that you need to be a founder, to build a company, and to solve a specific problem for a specific person, that can be your guiding light. Having that and focusing on it lets you embrace whatever your nature might be and work with that. The motivation is what’s most important, and everything else can be hacked.
This is not a post where I’m going to tout UpBuild’s growth numbers, our team/client retention, or our topline revenue. I’ll wait until our four-year anniversary for that. The results here are more intangible.
The result of all this (this entire ongoing experiment) is a company that I love leading and a job that I love doing. I wouldn’t trade this for anything, and there’s hardly a day that goes by where I don’t actively think about how thankful I am for the opportunity I’ve been afforded.
I think true leadership is about having a clear goal and working with others to get there. It’s about taking action and inspiring those who choose to follow you. It’s also about listening, about thoughtful consideration, and about resilience. I think that what I’ve found over the years is that while Type A extroversion is prevalent and makes for exciting conversation, Type B people and/or introverts can be in leadership positions and create very successful companies. It’s just a different approach. Type As and Type Bs are simply different tools, and you can use either to build something magnificent. In fact, I’d argue that if you have some of each (As and Bs) leading a company, the thing you build will be even better.
All I can share is my own experience, so I hope mine has been helpful to read about. If you’re in the same Type B and introvert boat (and even if you aren’t), I’d love to hear about your experiences with leadership in the comments.
Until next time, happy optimizing!