💡 How to Sell Yourself, 🎭 Overcoming Impostor Syndrome, and 💪 Making Sacrifices

PROGRESSION: 2025, Volume 6

Here’s a harsh truth I’ve learned over the years. Rewards don’t go to the person who does the best work. The rewards go to the person who’s best at showing others they’ve done the best work.

One of the most crucial skills to learn is how to sell yourself. That might be uncomfortable to read. It’s a little uncomfortable to write. When you interview for a job, the person who’s most qualified for the job rarely gets it. It’s the person who best articulates how the excellent work they’ve done translates to the company’s needs. You need to do great work and communicate that work. As we used to say at DoorDash, it’s “and”, not “either/or.” You have to have both.

Last week I spoke with a writer who’s preparing to publish his first book. I’ll call him Jack. Jack has spent the last two years writing what he thinks is an excellent book. Based on our conversation, I’m sure it is. He said he wants it to be a huge success, but he wants to keep a low profile. He’s uncomfortable with the idea of promoting his book. He wants his friends and early readers to spread the word for him.

I told Jack that there are two key steps for a successful book. The first is writing an excellent book. The second is marketing the book. I told him, “You just spent the last two years pouring your heart and soul into this thing. But that’s not enough. You owe it to yourself to spend the same amount of energy and effort getting this book into the hands of as many people as possible. If you aren’t willing to market and sell your book, no one else will.”

Learning to Sell

Many years ago, I joined a team of financial advisors at Merrill Lynch. Given that title, you’d think my primary responsibility was providing financial advice. I wish. It was cold calling. I would identify promising tech companies I thought would IPO in a few years. Then I’d make a list of early employees who’d have a ton of stock options. Then I’d call them at work (yes, people had work phones then) to tell them how my team could help them manage their stock options in advance of the IPO.

I did this all day, every day. Sometimes people yelled at me for interrupting them at work. Sometimes they called Merrill Lynch to complain about me. Once an HR department sent an email to the entire company saying I wasn’t allowed on campus. This didn’t stop me. I was looking for a needle in a haystack, but I found several new clients through this approach. Smile and dial. That was the game.

After almost two years of this, I was ready to move on. This wasn’t how I wanted to spend my time. I learned a lot, but I wasn’t becoming the person I wanted to be. I decided to get an MBA and pivoted my career to HR. It was an excellent decision.

Selling as an MBA Student

But the need to sell myself didn’t stop in the MBA program. A month in, I was interviewing for internships. It was a highly competitive environment and I had to articulate why my experiences and skills set me apart from others. This did not come naturally. I spent hours practicing on my own and with 2nd year MBA students. Ultimately I landed an internship, then a full-time job, at my top choice.

Selling at DoorDash

Fast forward several years and I’m leading HR at DoorDash. The need to sell remains. Only now I’m selling my work and my ideas rather than myself. My success is based on my ability to influence senior leaders to take action I think is necessary. I remember one conversation with my boss. I warned him that if we didn’t step in and intervene in a problem, things would get worse. I outlined an action plan. He listened but didn’t agree with me.

Months later, the problem grew worse. Much worse. My boss forgot our prior conversation and asked me why I hadn’t stepped up to solve the problem. I shared our conversation from months earlier. He told me, “Nathan, next time you need to be much more persuasive.” He put the onus on me, not him. While frustrating in the moment, he wasn’t wrong. In a rapidly growing startup, everything’s on fire. You can’t solve every problem at once. I needed to do a better job persuading him. It was my responsibility to help him understand the severity of the problem.

Selling as a Coach

I’ve been a solopreneur for three years now. I love my job. I work with interesting people and help them win the internal and external game. I help my clients see massive growth at work and beyond. Candidly, I think I’m a dang good coach. But my clients don’t just show up at my doorstep. The coaching space is crowded. There are a million other coaches promising similar results. It’s on me to show prospective clients who I am and how I can help them.

I sell my coaching services in a variety of ways. I have a website. I write this bi-weekly newsletter. I post on LinkedIn 3-4 times a week. Sometimes I’m very direct, but often I take an indirect approach. My goal is to add as much value as possible. When you’re ready to hire a coach, I want to be the first person you think of.

Putting myself out there on LinkedIn and in this newsletter can be very uncomfortable. I don’t always like it. I sometimes face impostor syndrome. I think, who am I to write this? Who am I to share lessons with people who may know more than me? But I have to fight through the discomfort. I believe in what I do. And if I don’t sell myself, no one will.

Summary

No one thinks about you as much as you. If you want your book to reach its intended audience, you have to put in the work to market it. If you want the new job or the big promotion, you have to learn to talk about your accomplishments. If you want to start or grow your business, you have to put yourself out there and sell. Your self-belief must be greater than the discomfort you face.

Maybe AI or some future invention will create a world where the cream always rises to the top and the need for communicating your value goes away. But until that day comes, don’t leave it to chance. Learn to sell yourself. You may not have to cold call like I once did. But you do need to identify your strengths and leverage those to sell your work in a way that drives impact.

Tim Ferriss said, “A person's success in life is usually measured by the number of uncomfortable conversations he’s willing to have.” Know that it’s going to be a little uncomfortable. Push through the discomfort. You owe it to yourself.

Learn to sell.

What I’m Learning

• One of my CEO clients recently shared his strategy for building his business. He identifies the biggest problem in the company and pours all his energy into solving it. Then he moves to the next biggest problem and solves that. Rinse and repeat.

  • This approach works in all aspects of our lives. What is the biggest thing holding you back from reaching your goals? Identify and solve. Do you need clarity on identifying where to start? Focus your energy on that.

  • I take this approach in triathlon. I want to get faster, but for years my running stagnated. I found two solutions: 1) I needed to be more consistent in my training, and 2) I needed to remove blockers.

    • To overcome these blockers I trained smarter, cut out sugar/desserts, lost a few pounds, trained with someone much faster than me, and purchased better running shoes.

    • Taking these actions culminated in a record half marathon last Saturday where I dropped 15+ minutes from my personal best (you can read more here).

  • Sometimes you just need to be more consistent. Sometimes you need to identify the biggest blocker and remove it. Often you need to do both.

• I was recently a guest on the People Managing People Podcast. I discussed impostor syndrome, psychological barriers that hold us back, and practical ways to reframe self-doubt.

• Baseball started a week ago and my Angels are miraculously 4-1 so I’ll share a favorite quote on the importance of sacrifice and hard work:

  • “Men don’t differ in their desire to win, they differ in the price they are willing to pay in order to have a chance to win.” —Roy Halladay

Gratitudes

I’ve found power in regularly expressing gratitude so I’ll continue the habit. I’m grateful for Kyle Fackrell. Kyle and I were roommates freshman year at BYU. We reconnected in 2020 when Covid shelved the Broadway play he was working on. He poured his energy into Space Race, a YouTube series which became a favorite of my kids.

He’s now in the final stages of his play, The Art Show, and is open to new investors. If you’d like to hear more, let me know. I’m grateful for Kyle because he’s relentlessly pursued his dream of creating a Broadway play. Despite many (MANY!) people telling him to move on, he’s pushed through and is realizing his dream. Keep going, Kyle!

If I can do anything to help you, please reach out. As always, thank you for reading.

All the best,

Nathan

Read my book, The Unconquerable Leader | Learn about coaching

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