Success, Failure, and Perseverance on your Professional Journey
As Presented to the Clarkson University Honors Program on 2022/02/03
Life has always been pretty challenging to cope with, and growth is a process that requires planning or a lot of failure and iteration. Here’s the thing: when you’re at the onset of your growth, you don’t know which way to grow. We’re not sunflowers and the sun is not obviously overhead. When you fail in your professional life, it’s really hard to figure out why you failed.
I’ve failed a lot. I’ve also tried to pull together (from my perspective) what the “typical” process of achieving command of your domain knowledge looks like, and then looked back at myself and how I constantly skipped around, failed out of stages, and then pushed through paths that were not “supposed to be” there.
Growth is cyclical, not linear. I find that being at stages of inexperience, general experience, and subject matter expertise status are good starting points for establishing a unifying theory for how individuals grow over time. You always start from the onset of the new paradigm you find yourself in, and getting to those key stages will help you envisage new horizons.
With the consideration for success and fail states as arrows across key stages of one’s own roadmap, I wanted to posit how I believe progression usually works, and counterposit my own experience.
What differentiates these paths? There’s no coherent cycle I’ve ever really followed aside from leveraging entrepreneurship-mindedness to jump into new paradigms which I fit into very uniquely (not necessarily “good” fit, just a very exacting and unique fit) via some combination of aggregate knowledge, or opportunities to grow. I was told over dinner by someone I advised that I don’t think linearly, but rather exponentially.
Of course I think exponentially. Do you think that, knowing 1 * 2 = 2, the only insight you might get from 1 + 2 = 3 is that 3 * 1 = 3? No: you’re going to have new insights, like discovering that 3 / 2 = 1.5. That is to say, from a new paradigm you always find yourself reflecting uniquely on your existing knowledge. You need to have that knowledge in the first place, though, because in every new place you will find yourself being inexperienced. Some subject matter expertise is critical before you shift gears and explore a new subset of information.
The Difference
The difference is that if you internalize within the learning process a robust self-assessment mechanism and pursuit of broader implications of your knowledge, you’re always developing vantage as well as your foundation. I learned this new thing. What does it mean? It’s not trivia, it’s connected to something else. What did you learn beyond the original lesson?
A lot of things can be derived from first principles, many of them quite trivially. It’s very simple to have a conversation as an expert with someone who is also an expert and stumble into something that, if you were to pursue via a standard path, you’d spend hours trying to figure out.
But you’re not born an expert. You’re born a dumb baby. So was I. That’s a fact of life. Fortunately, adversity can breed tremendous growth, and if you turn every single time you make a mistake into a challenge to better yourself, you can push yourself harder than anyone could ever push you.
Problem with pushing yourself is that burnout is ever looming, and you are really mean to yourself, you know?
So the key here is not just internalizing self-assessment mechanisms, because that mechanism can entail simply shouting at yourself for being dumb whenever you make a mistake: you also need to enact processes to better yourself, and keep yourself honest for it. You need to define the process and establish how you integrate your new experiences into the old one to build your vantage up. If you’re doing everything right and breezy it might feel good, but might also mean you’re not challenging yourself, maybe even getting complacent; if you’re getting beat on every day and just feel terrible, maybe you need to step back and reassess what you’re trying to do, because you can’t built anything tall on that kind of foundation.
Some key points:
Are you more effective at learning new skills from 0, or from a different place of knowledge?
Opportunity-cost is really hard, because it’s difficult to gauge what the best path forward is when you’re opportunity-starved, but keeping coherent priorities is critical in a world where you can become irrelevant in a few months from becoming complacent and hard to work with.
Always ask questions, and make sure you internalize that asking questions is always OK
Skills vs. Core Competency
What is a skill? I am qualified to do things with, my foundation is defined by, I extrapolate from, and leverage the skills I have to get things done.
What is a core competency? I am categorically capable within, perceive the world through the lens of, and am best poised to solve new challenges by interpolating within core competencies.
Skills and core competencies are inherently interconnected, but skills are tentpoles in the ground while core competencies are the cloth spanning between them, connecting the lattice of skills that you have into a tent of knowledge. Don’t learn things 1, 2, and 3: learn the domain of 1-3. It may be a little abstract, but pursuing multifaceted solutions which tie together different skills is always a lot better than applying them piecewise; why project-based coursework is usually better than extensive Q&A with a lot of little questions.
Ownership and Vision
You need to have a vision. You need to think of the future. You need a horizon to strive for. And you need to step back and ask why when you fail.
Maybe there’s something I could do differently. Maybe I’m approaching this all wrong. Maybe I don’t understand what success even is, so what does a failure here even mean?
I failed a lot, but I never just put my head down and kept pushing on through. I needed to take a step back and pivot, constantly. And you need to be flexible not just in mindset and approach but also about what you know and how others perceive that. Objectively I can say I’ve been an abject failure, but objectively I can also say I’ve been an absolute success. So I just… keep myself honest.
The roadmap:
Define destinations first
Establish your vision, establish keystone elements of your future self and career before you lose yourself in how you get there
Build a framework of who you need to be when you get there
Who do you want to be? What kind of things do you want to be squarely within your wheelhouse?
Turn high-level goals into low-level goals: “I want to lead teams” -> “I want to lead technical teams” -> “I want to lead technical teams building and integrating radios into satellites”, “I want to work on boats” -> “I want to work on boat hydrodynamics and navigation”
Sub-goals definition based on requisite skillsets and gaps
Who are you today? What is your current trajectory? What does the right trajectory entail? What are you missing?
Walk back from the destination using traceability, e.g. “to be a space operator I need to understand spacecraft operations, orbits, processes, regulations, and have an insight into the ground segment”, “to be a CMO I need marketing experience in X domains, established experience converting marketing into $Y in business, and Z00,000 followers on social media”
Reading job reqs you are wholly unqualified for is a good potential start, but it can also guide you to dead ends: it is possible that you might be building obsolete skills by definition this way
Establish an internal review process with consistent check-ins
Don’t lose yourself to your work: keep track of where you are and where you want to be. No trajectory is perfect on the first try, and you need to be ready to readjust
Some good things to review: how efficient you feel you are in your day-to-day; how fulfilled you feel in the work you are doing; how surmountable the challenges ahead of you seem.
Never stop decomposing the big challenges into little challenges
“This thing is so hard to do,” so why are you headbutting a wall like it will crack before you do? Have you tried learning how to work a drill?
Never forget to step back and reassess things when you’ve hit a roadblock. Maybe you’ve gone down the wrong path. Maybe you can bypass this wall and roadblock easily; this might have consequences or opportunities associated.
Define little discrete tasks that guide you towards those
Establish little steps towards significant pivots on your way forward.
Taking the metaphor further, don’t just drill through the wall. You need to get a drill. Charge the drill. Set up the drill. Get through that wall.
Pursue weird opportunities and ways to build yourself up
Refer to the review process and center yourself. Maybe reassess what’s behind that wall and if you’re really happy pursuing it, even if you’ve always wanted to.
Be flexible, and be ready to pivot, and be ready to jump into something new. There are a lot of opportunities out there to focus on things that fulfill you, that are a good fit for you, that let you make the impact you want on the world. Maybe instead of drilling through the wall, see what happens if you walk one street over. You’d be surprised. There are lower barrier of entries for parallel pursuits, and your vantage might help you see over that wall by the time you look back over.
Ask questions.
The self-review process is all about this, and you can only ever find alternate paths forward by questioning your original preconceptions as well as those given to you by others.
Maybe you don’t have to break that wall down by yourself. Maybe there’s someone on the other side of that wall. Maybe you can ask them some questions.
Don’t be discouraged by people who answer your questions with additional questions. Asking questions yields 1 of 3 outcomes, all useful: you get the answer; you get insight towards your question; you learn to not ask that person questions. There’s more people out there who will want to help you.
Never stop asking them how to break through, how they broke through, or whether they just wandered over from somewhere else beyond that wall.