The 11 Pieces of Advice I Would Give to My Younger Self — Thoughts on Building 'The Information'

Ten years ago, almost to the day, my husband Sam took a video of me curled up in bed, convinced I had food poisoning. I was so nauseous, I felt like I couldn’t move.

It turned out it was just nerves.

I had just told my parents I was going to leave a plum reporting job at The Wall Street Journal to start something new. It was the moment my decision to become a startup founder and to launch The Information became really real.

Sam showed me the picture a week ago (finally something useful came out of his record-everything habit!), and it got me thinking: What would I tell that young woman curled up in bed about what lay in store for her? How would I advise that less experienced version of me—and any other startup founder or business leader who feels paralyzed by a big professional risk?

As I look back on ten years of The Information, I am tremendously proud of our journalism and the fact that we’ve built one of the largest (profitable!) subscription businesses in news. I plan to carve out time over the coming months to reread many of the stories we’ve broken and reassess the industry changes that followed. I think it is also a good moment to step back and think about where the industry is headed in the next 10 years. Expect bold predictions.

But first, I wanted to measure out some of my own lessons over the past 10 exciting, eventful and, yes, nerve-rattling years. So I wrote out 11 pieces of advice to that younger me:

1. The hard things will be way easier than you think. The easy ones will be way harder.

You knew the journalism would be tough. And it is. Uncovering facts that powerful people are trying to hide requires relentlessness, intelligence and grit. But that will be nothing compared to the emotional toll of leadership.

Again and again, you will make a choice (a hiring, a firing, a business gamble) that is unpopular. You will feel lonely and attacked and exhausted by trying to explain yourself. Over time, leading through those moments will get easier, but it won’t come as naturally to you as reporting does. Recognize your strengths and weaknesses as early as you can and be willing to learn from them.

2. If you want things to change, change them.

Some time in the future, you will be trying to fix your morning editors meeting, where the team takes stock of the news we are reporting that day. It has gotten long and tedious and not very fun. You will stress about it for a few weeks before realizing you can just change it up. Now it’s your favorite meeting of the week. If something is not working, change it early and often.

3. It’s not just you: No one knows what they are doing.

You took a different path on your business model from the start. And people thought you were crazy. You weren’t. But every month, you will be confronted by someone with a very wise theory about what you should do. You will look out at the world and see so many people who seem so confident and have all sorts of advice. Listen to their advice but don’t assume they are right. Make the best decision you can and fix it if you screw up. Keep moving.

4. Communicate.

As a journalist, you’re used to synthesizing complex ideas and communicating them to readers. But it will take you years to recognize that you are not nearly as good at communicating with your team. You don’t prioritize it enough because you underestimate the degree to which the team finds it useful. Communicate consistently and your team will appreciate it more than you realize.

5. It is all about you…and never about you.

You will soon learn that the team will react to every word you say and mood you express—even what you eat for lunch. You will hate this but learn to accept it. You will soon have a very challenging time with a co-worker and won’t be able to figure out what you are doing wrong. You will soon learn that his cat died. Don’t read too much into things that have nothing to do with you.

6. Take time for people you care about.

Entrepreneurship is absorbing. You will have three kids you adore, and they will grow up too fast. Supporting your family and your team is all-consuming, and you will occasionally forget about all the other people close to you who believe in you—inside and outside the company. Lean on them when you need to and keep them in the loop, even if you don’t have as much time for them as you wish.

7. Keep going.

Your biggest strength will be your perseverance. Nothing comes easy, and you shouldn’t expect it to. But if you have enough energy to keep on going, you will get to the next level and then the next level—as long as you stay in the game. And if something is wrong (your sleep, an injury), fix it—or go surfing. And then fix it.

8. Take the feedback.

You are still working on this part. You appreciate the feedback you receive and you act on some of it. But you receive a lot of advice that aggravates you—generally the stuff you feel you have worked hard on and still haven’t fixed. Realize that honest feedback is a gift, and that when you are the boss, you can never get enough of it. So take it and keep the ones who give it close.

9. But think carefully about whose opinions you care about.

You will spend too long worrying about what outsiders think about you—the media reporter who won’t write about The Information, the banker who won’t invite you to his conference. Get over it and focus on your customers and team. Only they determine your destiny.

10. Don’t stop reporting.

There are days when you won’t feel very good at this job. Make sure to tap into your confidence source, which is also your joy. It’s the reporting. Call a source or two and break some news. Take the byline and smile.

11. Pause and give yourself some credit.

You will feel as you did in bed with the “food poisoning” again and again—but each episode will be shorter and more forgettable. Learn to be grateful for those nerve-testing moments and for the growth that comes out of them. And younger Jessica—good job.

This article was written by Jessica Lessin, founder and editor-in-chief of The Information. We are a global publication committed to original reporting and in-depth analysis of the technology industry. For full access to our journalism, subscribe today and save up to $250 on your first year.