👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on how to make high-stakes professional and personal decisions in your 30s.
The most common complaint I hear from employees at startups (including Section) is this: “The leadership team keeps changing the strategy.”
Of course they do. Startups are giant experiments designed to find product-market fit – they die if they don’t. So almost all startups constantly change and hone their strategy to figure out which product, packaged and sold to which market, can get to $10M+ (minimum) in annual revenue.
The problem isn’t the strategy. It’s that most employees have no idea what to actually expect when working at a startup.
They’ve been sold the “rocket ship” – a business that grows exponentially with tons of promotion opportunities and stock options that will be worth something. We sold this story to our new employees three years ago – as evidenced by All Hands slides that promoted “joining a rocket ship.”
But startups aren’t rocket ships. They’re roller coasters. They can be highly rewarding and serve as massive career accelerants. But they’re also incredibly demanding, stressful, and frustrating.
Here’s what we tell people to expect who are joining or working in startups. Use this list to avoid being shocked if you’re just joining a startup — or to assess whether your experience is emblematic of all startups, or just the one you’re at. Once you’ve read our advice, we’d love to hear yours – email us.
– Greg
The 10 things no one tells you
1. The strategy WILL keep changing – that’s a feature, not a bug. Startup strategy changes constantly. Your startup probably doesn’t have great product market fit, and periods of growth may be red herrings followed by periods of stagnancy or even decline. So your leadership team isn’t changing the strategy because they’re idiots (usually). They’re changing it because it’s not working, and they have to find more growth. You can excel in this environment by not complaining, paying attention to what is/is not working, and bringing ideas for the new experiments.
2. You’ll do work that gets thrown away very quickly … even if it’s good work. You could put three months of effort into an initiative at the beginning of the year, and it gets killed before launch. The upside of this is you’ll also do work that gets used immediately. So don’t take it personally, when some of your projects/initiatives/great ideas end up DOA – and take credit for your ideas that get implemented and actually work.
3. “Opportunities for growth” often means doing 2 jobs. “Growth” in a startup means “having more impact,” not necessarily promotions or raises. If you’re not willing to do two jobs, you likely won’t be happy at a startup. You won’t get paid twice as much for the second job – the whole reason you’re doing it is because your startup doesn’t have the money to hire two people. The benefit is more responsibility than you’ll get anywhere else, and experience you can speak to at other startups. And maybe you learn that the 'second job’ is actually the role you want.
4. You’ll be given a job you have no idea how to do. You’ll be given roles, tasks, and projects you’ve never done before. This comes with lots of upside – startups are the fastest path to lots of responsibility early in your career. But expect to be uncomfortable, nervous, and out of your element often. There’s usually no safety net, so the stakes of your job will feel higher. Some people (including us) love this challenge. But if you don’t, startups might not be the right fit.
5. Your boss’ sway inside the company is your promotion path. Big companies have promotion paths, review cycles, and other levers to accelerate you through the organization, no matter who you work for. Startups don’t. Your boss could be the best mentor and advocate in the world – but if they don’t have influence and power in the organization, your potential will be capped. If your boss is one of the 2-3 most important people at the company, their projects and exposure will trickle down to you. If no one listens to them, they won’t pay attention to you either.
6. Promotion and bonus budgets are non-existent. Once in a while, your manager might have the budget and influence to support a large raise, so you can end up with faster salary growth than at a larger organization. But most of the time, budgets for raises and promotions at startups are much smaller than you think. It’s why managers rely on title changes and higher-impact projects.
7. Availability (not necessarily long hours) is rewarded. Lots of people say work-life balance is nonexistent at startups. It depends how you define work-life balance. Sometimes you will work long hours. But for the most part, it’s less about the quantity of hours, and more about remaining checked in (aka, available on Slack) after 5 PM. Startup leaders are eating, breathing, and living the startup – therefore, they’ll reward others that are available and responsive in the moment, even if that moment is Sunday afternoon.
8. Outcomes, not process, are rewarded. Your CEO does not care if you put a ton of work into something if it doesn’t translate to outcomes. Before you spend 20 hours improving the brand style guide, ask yourself: “Will this help the team do better work that I can measure when it’s time for performance reviews?” If the answer is no, spend 2 hours, not 20.
9. It’s about relationships, not stock options. You’ll go through more highs and lows with your startup colleagues than almost anyone else in your life. They’re also likely the strongest, smartest colleagues you’ll work with (because startups are picky … and sink or swim). For these two reasons, people who work together at startups often work together after. Both of us still work today with colleagues from our previous startups.
10. You have an opportunity to be one of the most important people in the company. The biggest benefit of working at a startup isn’t promotions, raises, or a logo on your resume. It’s the opportunity to be integral to an organization’s progress. This comes with downsides (namely, stress). But it’s also much harder in a large company. If you’re someone who hates being a cog in the machine, and needs to see the immediate and visceral impact of their work, there’s no better place to work.
Our advice
In his book “Tribe: On Homecoming and Belonging,” Sebastian Junger writes about the powerful bonds of tight-knit groups, particularly when formed under stress or hardship. He writes about military units, but the same is true in startups. They’re not life or death, but share similar characteristics – a shared sense of purpose, hand-picked teams, long hours working under stress.
So it’s not surprising that lifelong friendships are formed at startups. And it’s not surprising that a year of startup experience is equivalent to three years at a large company. In the last two years at Section, Taylor has learned how to manage a P&L, forecast revenue, boost team morale, do layoffs, and pivot a business. That experience would have taken a decade at a larger company.
At the end of the day, these are the two reasons to work at a startup: the people and the personal growth. But go in prepared for the roller coaster, not the rocket ship.
To the next 10 years,
Greg and Taylor