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Many people working at startups change jobs frequently, while employees of big companies may toil in the same place for decades. 😢

If you work at a megacorp today, how do you know if you’re ready to make the big leap to the startup world?

Here are 5 questions to ask yourself:
1) Are you capable of working in an unstructured environment?

Here’s the thing, even in well-run startups, there’s nothing like the command structure, hierarchy, and clear roles of a huge megacorp.

Big companies thrive on deep layers of people and titles and information.
Startups require you to make progress despite ambiguity. Often times deep ambiguity.

Features aren’t in planning for months. There’s no internal handbook describing exactly how your role works. Every “first” has to be invented.

You kind of have to figure it out on your own.
For some people, this ambiguous startup environment is enthralling because it is all opportunity and growth. Not having everything already structured means YOU GET TO STRUCTURE IT.

It can be so fun to be at the earliest stage of building not just a product, but a company itself.
For other people, the deeply entrenched structure of a big company is perfect: predictable, clear, and won’t rapidly change.

Be honest with yourself about how excited you would be to work in a more fluid, early-stage environment. It’s not for everyone (and that’s ok!)
2) Do you have a relevant skill set to be considered at a startup?

By their very nature, big company roles tend toward specialization. As a dev in particular, you are rewarded in a megacorp for building deep tribal knowledge of labyrinthine internal code bases and technologies.
This specialization often comes at the cost of broad experience with open source projects. Megacorps tend to have not-invented-here syndrome with code.

When I worked at Microsoft, often the entire stack from the pixels on screen to the compiler was all Microsoft-internal code.
In a startup, you are often gluing together solutions with public code from disparate projects, figuring out to integrate them together in a elegant way.

Much more of the code you write will actually be building product value, vs. just feeding the internal engineering system.
3) Are you comfortable with the financial tradeoffs?

Startup compensation works differently than it does at big company. The offer may look strange compared to what you are used to, and include unfamiliar components.

You need to evaluate a startup offer differently.
Typically, a Microgoogfaceforceazon-type job includes base salary, a potential bonus based on pay-for-performance, and some stock ownership.

The stock component is often called “golden handcuffs,” because the megacorp has to handcuff you to your job to get you to stay. ☹️
The entire megacorp job offer can be thought of us cash. Sure, the stock might go up or down a little, but there's not much that a single employee can do individually to influence that.

As a result, the income is predictable and safe, with little upside but also little risk.
Startups, on the other hand, offer significant equity in the company as a highlight of the offer. Yes, the cash part of the offer will be competitive, but rarely as much guaranteed cash as the megacorp.

What you have instead is actual company ownership with a tremendous upside.
Unlike in a big company, YOU can actually individually influence the success of a startup. You can have a material impact on the worth of your equity.

Startup equity upside is all about 100x growth, not 10% growth. It is exponential.

Or it could be worth nothing—hence the risk.
In the end this is a personal choice, and you need to be honest with yourself about your priorities.

If your goal is to max out guaranteed cash earnings in your 1st year, a megacorp will almost always win.

Consider, though, why they have to overpay people so much to work there.
4) Do you love learning?

Startups are all about learning. Not book learning, like reading Plato’s Republic (usually), but about rapidly assimilating new skills.

Figuring out what you need to know to solve hard problems, and then turning around and doing that again and again.
The single characteristic that has most equated to success for people at our startup is demonstrated capability to learn new things.

I can’t predict accurately what skills you might need in 2 years. But I know if you are great at learning, you can pick up whatever you need to.
If you love to learn new skills and then immediately apply them, you will flourish nowhere faster than at a fast-growing startup.

While adeptness at learning won’t necessarily work against you in a megacorp (though you might get bored), in a startup, it is absolutely required.
5) Do you enjoy working collaboratively?

Not everyone does. As an extreme introvert, I have struggled with this in my career.

Yet, in a startup environment, true collaboration is frequent and necessary; people simply must work closely together or the company will fail.
That is not to say that all startup work is collaborative work.

I actually loved the first few years in which I often went for days at a time without a scheduled meeting, being able to just put on my headphones and code the entire day without interruption. That was bliss.
In fact, in a startup much less of your time is spent on “status update” meetings and “report outs to the boss.”

But, the work that you are doing relates directly to other people. Not just to a line item on someone’s schedule. You have to figure out each piece with others.
Because you are building through ambiguity, inventing the product while you code it, finding product/market fit while you market and sell it, necessarily everything you do is with other people who are also inventing & discovering.

A high-growth startup means collaborative work.
In the end, the choice to leave the megacorp world behind is a personal one. Big company life is safe and predictable, while a startup can propel your career forward like nothing else.

Ask yourself the right questions (and be honest in answering) and you will be on your way! 💫
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