Externally, I am a confident person. I can carry myself in meetings, I’m not a bad public speaker, and I’ve taken enough leadership courses to understand I tick a decent amount of the boxes. Internally, however, I am not nearly as confident as my outward persona might have you guess. I’m no stranger to anxiety and, while they decrease as I continue through my career, there are plenty of moments I ask myself if I belong on a certain project or in a certain room. Classic Gemini.
And let’s be clear: I am fully aware that I am an overeducated, cisgendered, heterosexual, white male. Despite what 4Chan might tell you, that’s still an advantage in American (and Western) society, however unfair that may be. And while society may allow me to more easily belong because of all the hard work I did to be born into a white middle class family in a good school district, I am a big nurture guy in the showdown with nature. There are strategies to building one’s self-confidence, and it’s a massive advantage in the Western business world.
Know Your Stuff
I used to be terrified of flying. I’m talking panic attacks days before my departure and being on edge through an entire trip, only to collapse at home exhausted when it was all over. One of the ways I overcame this was to acquire as much knowledge as I could about flying - the physics of it, the operational aspect at major airports, the routines flights typically maintain. I could tell you what all the dings mean in the cabin, the physics of drag and lift, and why really the only time to be nervous is if you see red nd green alternating light beams from an airport’s control tower.
I did it not to become a pilot (although if I ever hit lotto one of my first purchases will be a single engine prop Cessna), but to gain back some of the control that is lost by being a passenger by learning as much as I could about flying. I used that as a springboard to power through it when I got put on an account that required a lot of travel, and I’ve been golden ever since.
So if you’re feeling insecure at work about a particular project or team you’re on, one early step is to dive into the work product for it. Research the hell out of topics that pertain to the workflow. Become an SME in something necessary for it. Do everything you can to remove that kernel of doubt nagging you that you’re not good enough for your position by acquiring knowledge. It sounds corny, but knowledge really is power.
Contribute Consciously
Now that you’re well-versed in your work, you’ll find yourself in more meetings. It may be a super senior meeting where you’re to simply be a fly on the wall, but there’s still a role to play. It’s an opportunity to absorb something and to bear witness to how decisions get made or strategy hammered out (warning: you’re not always going to be impressed with what you see.) There are ways to contribute to a meeting without talking, and at the very worst it’s an opportunity to absorb and further learn.
But you might also be there to contribute. If you know this is the expectation, it’s not a green light to run your mouth about all of the knowledge you had acquired from the previous section. It is a skill to listen and contribute at opportune times and in meaningful, succinct ways.
If you’re in a competent organization, you will notice that the highest ranking person in the room is one of the last people to talk (outside of potentially kicking off the meeting.) If they jump in too early, it sways the more junior people in the room to agree, or at least water down their opinions if they go against the boss’s.
If the boss talks the whole time, drowning everyone else out and not accomplish much, this is a huge red flag. Meetings like that are ego-driven - not results-driven - and the lack of productivity can only roll downhill.
The best bosses I’ve had didn’t tell me what to do - they asked me questions to let me come to my own conclusions on the next best step forward, providing guardrails where I threatened to divert too far.
But back to your role: don’t shrink into the corner - this isn’t Basketweaving 101 to boost your GPA. Take your cues from the room and settle yourself somewhere that feels comfortable but elevated. Chances are, you’ve earned it.
Find Your Intrinsic Driver
I’ve mentioned before that I find myself very extrinsically motivated. I want the title and (more importantly - this is America after all) the money associated with good work and upward career progression. These are excellent carrots for an employee like me to have dangled in front of them as motivators.
But they only go so far. Especially in advertising, which is particularly sensitive to macroeconomic downturns; promotion holds and hiring freezes occur often enough that you need a backup plan. When the power goes out in a storm, what’s your backup generator?
And that’s where the intrinsic motivator comes in. When things are on hold extrinsically, what continues to drive you to do good work? For some lucky people, the mere goal of a job well done is enough to get them through the day regardless of remuneration or promotion or whatever other shiny object is the ostensive reward.
While that’s part of my intrinsic motivation, it’s not the whole (or even the majority) of the story. Through a decade of therapy and self-reflection, I’ve determined that my main intrinsic motivator is never feeling like I’m good enough. Growing up As were great, but were A+s possible? If I pitched 5 innings of shut-out ball but gave up a single run in the 6th on the way to a W, guess where my focus was post-game.
This was cemented when I was lucky enough to go to a private prep school, which combined the ethos of “You are very smart and special to be here” with “You are a shame not only to this school, but also your family name.” The mix of positive and negative reinforcement was incredibly effective at pushing us to do our best regardless of whether the chips were up or down.
And that insight has been incredibly helpful as my backup generator when the extrinsic motivators aren’t providing the energy I need. By harnessing that intrinsic motivator that was nurtured in me via a uniquely New England-style cognitive dissonance of accomplishment, I can use what used to make me question my credentials to enhance my confidence.
But this is only possible because I’ve been able to realize it. Nearly everyone suffers from imposter syndrome at some point - the key to overcoming it isn’t necessarily self-confidence. It’s tackling the reason you’re feeling inadequate. The lack of self-confidence is a symptom of the underlying problem. Figure out the problem and the self-confidence will follow.
Grab Bag Sections
WTF Highway Drivers: I had the pleasure to drive from New York to Boston and back this past weekend. And boy do I have notes.
The northeast corridor has not figured out what the Italians have: the left lane is for crime. If you’re not going 15+ over the paltry speed limits on the interstate, you do not belong in that lane. The utter lack of self-awareness of people in the left lane as they have a line of cars behind them and nothing but open road in front of them should be an arrestable offence.
Finally, embrace the zipper method. As we encounter closed lanes from the perma-construction on the web of interstates between these two cities, it might seem that the right thing to do would be to get over as soon as you can to help traffic move past the closed lane. Dear reader, you would be wrong. You should use the entirety of the open lane and merge at the point of closure for the most efficient process. This would, of course, require a patience and “we’re in this together” attitude for which Bostonians, New Yorkers, and especially Nutmeggers are not exactly known.
Album of the Week: We’re heading to the West Coast this week for Dr. Dre protege Anderson .Paak, whose LA-themed albums have won him critical acclaim. The second of the three, Malibu, is where we’ll focus today.
An excellent intro to Paak’s style is “The Season / Carry Me” where he mixes two songs into one. If it’s vibes you’re looking for, “Room in Here” (including a solid The Game feature) and “Celebrate” are where you should go. While we keep a family-friendly atmosphere on this newsletter, “Silicon Valley” has horns and backing vocals on the pre-chorus that you shouldn’t miss. Paak ends the album with a strong outro in the Talib Kweli-featured “The Dreamer.”
Quote of the Week: “Believe you can and you're halfway there.” - Unknown (often misattributed to Teddy Roosevelt)