8 Career-Building Insights I've Learned After Working At Five Startups

Should I go back to school? Change career paths? Or switch to an entirely different field altogether? A friend asked me these questions over coffee, and my rather simple and straightforward reply was:

Screw those, go work for a startup.

I’m well aware of how crazy startup life can be. I’ve worked for five of them. And I still believe they are fertile grounds for growth, especially if you’re fresh out of school. As cliche as it sounds, startups are where failures lead to learning, experimentation is encouraged, and no two days are the same.

Those who want a change of pace or desire to hone new skills should consider taking that leap to startup life. I did that years ago. Five startups and many lessons later, I have no regrets, because I’ve learned 8 key lessons that have since shaped my thinking in both my career and life.

1. Don’t ignore the need to build rapport

It’s no secret that startup teams are usually small. You’ll be working with the same hungry faces, day in-and-out, so you’d better be on good terms. Building good rapport removes barriers to collaboration. Permits vulnerability during meetings. Removes the sting of feedback. Good rapport makes for happier and friendly teams, which can only benefit everyone.

How do you build rapport? Buy a busy colleague coffee or lunch. Celebrate their victories, big or small. Offer your help with their workloads. Teach them a new skill. Be sympathetic to their struggles, open to their shortcomings. It’s these simple things that turn colleagues into lifelong friends.

Startups aren’t just fertile grounds for your career; they are also excellent places to nurture your budding work network.

2. Be okay with being thrust on the spot

When it comes to startups, it’s easy to track who’s doing what. It’s also easier to determine who messed up when the proverbial shit hits the fan. Everyone gets put on the spot once in a while — even a startup’s founders. Learn to be accountable. Be responsible. Be okay with owning your mistakes.

How should you deal with this? When the inquisition happens, don’t take it personally. Mostly, it’s because teams want to diagnose and solve the issue before it grows. You can help by presenting possible solutions to the table. If it was your issue, you’d be in the best position to do so. In every bad situation, lies an opportunity to turn things around and improve.

3. Expect to get stretched a lot

I was once asked to rebuild the company website, all on my own. I had zero knowledge of coding and a rudimentary knowledge of WordPress. For weeks, I had to stretch myself by speaking with different people, learning new skills, then piecing code together. That’s the typical experience of most startups.

Here the path diverges. It’s a dealbreaker for those who want stability and familiarity in their jobs. You’ll need to be proactive and resourceful, or you need to learn how to fast. Embrace and cherish the practical opportunity to make mistakes and learn on the job — it’s a chance rarely found elsewhere.

4. Don’t be afraid to share ideas

One of my founders was pretty big on sharing ideas, which was unusual for the startup industry. “Shared ideas could be stolen,” conventional wisdom says, “so hold those cards close to your heart.”

Consider those words of wisdom, and share anyway. Yes, putting your cool ideas out there poses a huge risk. They could be indeed be taken from you. But on the flip side, it allows your friends, colleagues and founders to suggest improvements, highlight issues or offer support to bring the idea to fruition. Their feedback might even lead to new idea pathways for you to explore

5. Find a cause you can resonate with

You’re going to be sweating buckets and working your butt off, so it better be for a cause you strongly believe in. I cannot stress this enough. Looking for financial gain? Look elsewhere. Only people who aim to shake mindsets, uproot foundations and move mountains, need apply.

So what should I do? Ask yourself, what would help you leap out of bed every morning? Figure out the industries that relate to those causes, then dig around for startups in those industries. Attend conferences, follow startup blogs, attend hackathons and incubators. Then go introduce yourself.

6. Stop and pause occasionally

When confronted with a problem, one of my bosses used to sit back and stare into space. It wasn’t indecisiveness; he was using the awkward pause. Startup life can be frenetic, the competition unyielding, but it’s wise to pause and really think things through, once in a while. Making decisions on instinct and acting with haste has saved many a startup, but it has doomed others as well.

How should I approach this? I once made a hasty decision that resulted in a $2,000 loss for the business. Small loss, but still painful. To avoid a repeat, I created a 3-step framework that has since led my decision-making:

Does it make sense to others? I run decisions through 2–3 people. Does it click with them? No? Back to the drawing board.

What benefits will it bring? Will it improve customer service? Create loyalty? Improve efficiencies? Would this help the customer or client?

Has there been a similar decision? No point overcomplicating this. Ask around, and note how the decision was made. Was it useful? Did it improve something? Did it bomb? Then adjust your plans accordingly.

7. Champion value in everything you do

One thing you quickly learn at startups is that every move, every decision, every product is calculated against a rubric of value. And this rubric is almost always about the customer. Would this tech streamline their hiring? How can this service improve their health? Is this something they would recommend to their friends?

Value for the customer = sale for your startup. And that sale, in turn, is the value that keeps you afloat.

How can I ascertain value? Put yourself in your customer’s shoes. Employ the outsider’s perspective. As a customer, would I really be tempted with what your startup has to offer? Will it really make me better, faster, stronger? As a marketer, this is second instinct, but it can be nurtured with practice.

8. Remember to enjoy the journey

This has gone on for long enough, so I’ll keep this brief. Remember to enjoy your journey. If this is your first job, enjoy your formative years. If this is a break from corporate, enjoy the new rush. I promise you’ll be a different person when you emerge on the other end.

If you’d like, I recommend journaling your startup journey as well. Write down your takeaways; it might be similar to mine, but it would most likely be different. Mull on them and consider how they can be used to shape and improve your career and personal life.

If you’ve worked at a startup before and have a takeaway not listed here, feel free to share below. I’d love to read what you’ve learned as well.