I’ve held a variety of roles at organizations of different sizes, but by far the most success I’ve experienced is in the environment of an early-stage, fast-growing startup company. It’s an exciting place to operate, the momentum and fast pace feels amazing to be around. The sense of progress and “building something” is palpable, optimism is in the air.

Of course, like all things in life, there’s a trade-off. A fast pace means high pressure. Momentum means higher expectations. Excitement also means uncertainty. Potential for huge wins necessarily means potential for huge loss.

Most of the time, all we hear about are the success stories. This survivor bias has created a skewed perspective on being early-stage employee in the public eye. I have thoughts, and this post is my attempt to explain the reality of what it’s like.

The Rocket Ship Metaphor

Startups are often compared to “rocket ships”: once they “launch”, they “accelerate” into “the cloud” (ha ha). I think this metaphor is apt. Rocket ships aren’t very impressive on the ground before they launch. They’re filled with fuel and are known to explode everywhere and hurt people. Once they get off the ground they produce an enormous amount of smoke and noise, at first it’s hard to determine if they’re making any progress at all, and the vibrations throughout the frame will cause the crew to feel like they’re being shaken apart. They leave some scorched earth behind them in their wake. Once they make it into space, they’re untouchable and don’t easily return to earth.

Don’t let the recent successes of SpaceX bias you: the vast majority of the time, the rocket explodes. Like 99% of all rockets ever launched blew up. Also a boatload of rockets that were supposed to launch never even made it to engine ignition.

Rocket ships are amazing but they are risky. Do not enter the blast radius unless you are prepared to get exploded. This applies to rockets and to startups.

Scaling Yourself

Every day in a startup is a new day. New problems. New customers. New scaling issues. Each day is an adventure, and that keeps things interesting! Except there’s no boundary or threshold to change. You don’t get to a certain level and get to relax. The prize for winning the early-stage startup game is: a mid-stage startup. Those are even harder to do properly and even more liable to explode in your face.

Yes, you might get a “vacation” after the team is big enough that you aren’t needed all the time. But that vacation will include you stressing about how things are going without you, your unconscious mind will be solving code problems from last week, or your vacation will literally be interrupted by some “unsolvable” problem back in the office. Founders never get a break from thinking about their baby, but you as an early employee won’t get a break either.

Often times you will be told you need to “scale yourself” in accordance with the new demands of whatever stage the company is at. Usually that means hiring somebody to do the job that you used to do. That means replacing yourself with someone better than you at that thing. Scaling yourself is inherently robbing you of your explicit utility to the company. To stay relevant you must reinvent yourself, constantly.

If you ever stop reinventing yourself, even for a short time (a few weeks, a few months), you will demonstrate your inability to scale and you will be replaced. If you’re “irreplaceable”, efforts will begin to make you redundant. The startup and it’s founders are not your friends. They need you to do a thing, and if you can’t do the thing, you’re not going to last long.

That’s just the harsh reality. Loyalty means nothing when you’re getting a paycheck. Assume you’re hard work has already been compensated for, and never rest on your laurels.

Failure vs Success

Throughout the course of my career, I’ve realized that I’ve learned far more from my failures than from my successes. Every single time I failed, there was a reason (usually many reasons) that are worth reflecting on. Failure is a signal pointing to your flaws. If you listen, you can get better. If you don’t, you’ll stagnate. Even if you were betrayed, you failed by putting your trust in people who didn’t deserve it.

Success is different though, since you can experience success without it being directly tied to your behaviour. Maybe you got lucky (it happens), maybe you got carried by your team, maybe you worked real hard for it, maybe maybe maybe. You don’t actually know why you succeeded. Even when you get a good outcome (financially), that doesn’t mean you deserve it, and it doesn’t mean you can repeat that playbook again with the same result.

Failure brings humility. Success brings arrogance.

As soon as you start believing your own bullshit, you’re lying to yourself and everyone else. Stop it, or else.

I’ve made this mistake and confused my arrogance for wisdom. I presumed that past success guarantees future success. It’s brought me nothing but misery and hardship. This is an extremely hard lesson to learn. If you’re not expecting it, it might break you entirely.

When to Quit

The rocket ship ride is incredible, if you make it to space. Hold on for dear life, and if you’re lucky it’ll be the best thing you could do for your career, your confidence, and your financial situation. If you let go even for a minute, or if your rocket is destined to explode due to some design flaw or just plain bad luck, it’s going to be painful. But at least you can rebuild the rocket and not make that same mistake.

As you scale yourself and your startup grows, you must become better at evaluating performance and making hard decisions. That means firing people (even your friends) when they aren’t working out. Ultimately, that means managing yourself out when you no longer have gas in the tank. Don’t expect your company or your founders to give you anything you haven’t earned, just out of a sense of loyalty. As previously discussed, loyalty is dead and you’ve already been compensated for your work.

In my experience, when you start getting feedback that makes you feel defensive and powerless, that’s usually a good sign that you’re failing to scale yourself. Feedback is a gift, and if you defend yourself, explain yourself, excuse yourself, or rationalize your behaviour, you’re rejecting this gift. This pattern of behaviour is self-destructive, and if you dig your heels in you’ll find yourself out of a job.

Sometimes there is no path to improving or scaling yourself in response to feedback. If you feel stuck and frustrated after a few feedback sessions, it might be time to consider firing yourself, on your own terms. Find a soft landing. Take some time off. Remember that any resistance to change is resisting growth, and without growth a startup is dead. There’s no shame in managing yourself out. Do it before it gets done to you.

Final Thoughts

If you’re an early employee struggling with any of this, if this post resonated with you in any way, or if you feel alone for whatever reason, please reach out to me at anson@mackeracher.com. You’re not alone in this journey.