Startup or Enterprise, A Tale of Two Careers
I’ve been asked a lot over the past couple of years to discuss what its like working at a Startup given my work history is mostly larger companies.
To put some context behind my thoughts its worth noting that both of my recent employers (CoreOS and Heptio) have been fantastic experiences, but were not in fact my first stints in the Startup arena, however given that my Startup origin story is quite a bit dated I’m going to stick to the more modern material.
I couldn’t come up with a good structure for this without giving away details that are still a bit too fresh for me to disclose. Instead the below is just snippets based on both facts and my own experiences that you hopefully find useful.
One thing is for certain — while HBO’s Silicon Valley has some truth in it, building a Startup is definitely not like that for most.
Why Work at a Startup?
The idea of being part of a team of people scrambling to build a business from nothing sounds appealing.
You like the sound of doing a lot of hard goddamn work and enjoy learning on your feet more than learning from others.
The idea of change and flexibility appeals to you. New roles, new locations, new co-workers, new products. Its all going to change a lot.
You are okay with going it alone / being lonely. This is mostly true for executives / department heads and founders in particular.
You can handle, and maybe even enjoy an emotional rollercoaster. The joy of winning / creating is amazing (highs) but the constant struggle and frequent failures (lows) often lead to many burning out or feeling stressed out all the time.
You want to do something incredibly rewarding (assuming things work out), in almost all circumstances working at a startup is sort of like a time dilation bubble for your career. You get more experience, faster and in a broader array of scenarios.
Why Not Work At a Startup?
It is not easy.
It is not a utopian panacea of feel good stories and people playing foosball.
Compensation is generally lower. The tradeoff here is the career growth and flexibility. The younger the company the crappier the (immediate) compensation but the more growth and flexibility you’ll have.
Despite what pop culture would have you believe there is very little time for you and your friends to hang out at work. Sure you know them, and you like them, but you’ll have no time.
You are impatient. The average startup takes 7 years to exit. Most never do, and unless you are one of the first dozen employees or a high ranking executive the average payout is nice but not life changing. Basically it is a long slog.
You will not have as much influence or input as you think. Sure if you are employee #7 (as I once was) you will have a lot of input … for a while, but the goal is to grow the business.
As that happens your influence dwindles. By the time a company reaches 100 people the executive team has exceeded their Dunbar number and the company is becoming something else.
Why Work at an Enterprise?
You value stability at work, the same day to day job is A-OK with you. Planning for the long term is your norm.
Immediate compensation and benefits are a significant concern for you.
You want to bolster your resume with a household name. Everyone knows who American Express and Google are. Not many recruiters or hiring managers know Startup #231.
Mentorship and learning from experienced industry veterans is something you value and would serve you better than being thrown into the deep end.
Why Not Work at an Enterprise?
You want to feel highly valued as an individual / person. Most large companies fall flat here. Sure you may land with a good Manager or Director but by and large you are just a line item.
You prefer high energy co-workers and modern work environments. Most enterprises operate in office parks built decades ago, with long commutes for most employees the general vibe is lower energy and more work-focused.
Rapid changes in work focus, work environment and individual assignments is something you need to thrive.
There are a lot of considerations to take into account and this is just the start. I think for most people over the course of their career that bouncing back and forth between both types of companies provides the biggest personal and professional benefits for you.
This allows you to both learn about different phases of business and about yourself and how you handle different circumstances while also choosing when to accelerate your career or compensation as needed.
Its also worth noting that while Startups are often perceived to be a young persons game, thats not really true. Sure the age trends a bit younger for specific roles and company types.
A big reason for that is the number of people who can afford to take a financial risk within each age bracket deviates based on a number of factors such as medical concerns, having kids, dealing with aging parents, saving for retirement and similar.
These concerns should certainly be at the forefront of any decision making about what company you should land at if you are deciding between offers as many Startups do not have as robust a set of benefits or compensation as their larger counterparts (instead relying on equity and the time dilation effect I noted above).
