250,000 to 40,000 to 10.

These numbers sound like a frightening drop, but this sequence represents the best series of decisions I’ve made.

It’s the number of employees at the companies where I’ve worked.

After 5 years at one of the largest companies in the world, 2 years at one of the biggest business schools, and a summer at one of the “best places to work” according to basically every publication out there, I decided it was time to venture into the unknown. No, I didn’t hike in the Himalayas or backpack through Siberia. I joined a startup, which I would argue, is not unlike a rigorous hike or extensive backpacking tour. Over time, in all three cases, it gets more comfortable. You get used to the bumps in the road, the altitude sickness, the cold, the wild animals, and it begins to feel almost good, and finally, you realize that you totally fit in the wilderness.

Like any good guide, I’ve prepared some advice for those transitioning into the wilderness of a startup:

Three things I’ve learned:

  1. Learning by doing is the best way to learn. Its natural to feel like you should be really well prepared for something before you dive in. But what I’ve found working at a startup, is that sometimes you just need to move ahead. Experimenting and iterating is one of the best ways to create a really valuable product because you gain real feedback and can change based on that. It also allows for more opportunities to learn, since you’re constantly reinventing things and putting new products or content out there.
  2. You have a powerful effect on the people around you. Negative energy is very powerful, especially in a small team. When I’m feeling discouraged or down, I can see that it has an effect on my teammates, and not in a good way. This has made me much more conscious of my behavior and energy, and how important it is to stay positive.
  3. Every day is a new day. Each day at a startup is a rollercoaster. Actually, each hour is. There are so many ups and downs, and bumps along the road, which means its so important to stay level-headed, keep perspective, and remember that every day is a new day to wipe the slate clean.
Three tips:
  1. Assess the worst case scenario. If you’re comfortable with that, then do it. this philosophy is  also helpful during the tough times when you doubt yourself.
  2. Create a unique value proposition that you can bring to a startup, and own it. It’s important to really understand what you bring to the table. It can be in multiple areas of expertise and across several functions. In small teams, being a jack (or jill!) of all trades is actually more valuable in some cases because it allows the team to remain lean but still have a broad skill and experience base. It’s also really important to be confident in your abilities. It’s often harder to execute at a startup because it can seem like there will be greater consequences, which means you need to put self-doubt aside and just move forward.
  3. Integrate yourself in the broader tech / startup / (whatever’s relevant for your startup) community. Being at a small company means you have a smaller daily direct professional network, so make sure you’re immersing yourself in a larger one. Its also a great way to recruit, get yourself and your brand noticed, and develop new business.
In the end, I have no regrets. I work with an incredible team, doing work that I enjoy, and every day I learn something new. There are ups and downs, but joining a startup has been a great adventure for me, and I’d love to hear from you if you are thinking about making the leap!