How to Stop Comparing Yourself to Others (Without Hating Yourself)

"As of this week, my personal net worth has hit nine figures," my client said.

It took me a moment to sort what that meant.

One hundred million dollars!

Wow, I thought. That is a big number.

In coaching, part of what we train for is to notice our thoughts, reactions, and emotions in sessions. We are taught to identify them so we can set them aside and remain present for the client.

At this moment, what I noticed was I felt simply happy for my client. It was not happiness about his riches, although that is super fun. It was happiness about his happiness.

When I was digesting the session later that day, I realized this experience was novel for me. For years, whenever I heard about the success of another founder, I felt wracked with self-criticism. The success of someone else would send me into a spiral for hours or even days.

Noticing in that session that I felt none of that was a big step for me.

If you want to stop comparing yourself to others, the goal isn't to never notice success. The goal is to stop spiraling.

As a coach, I spend time around founders who are in the midst of tremendous success and founders who are in the midst of soul-crushing struggle. Equanimity about the success of others does not come so easily every day. There are still sessions where the achievements of a client are triggering to me. In those moments, the questions that pop up are:

• Do I need to do something bigger?
• Am I achieving enough [money, impact, fame]?
• Should I stop coaching and start another venture-backed company?

The thoughts still come from time to time. But they come, and then they pass. And I am so grateful. By allowing them to pass, I can simply be with the human on the other end of the table or screen.

Like an addict is always prone to addiction, and always 'in recovery,' I may be prone to the pain of comparison. But it is so much better than it used to be.

I have learned a great deal about how to disarm the questions, how to sit with them, and how to ensure the triggers do not ruin the day or prevent connection.

Here's what comparison steals, and what helps.

Why we compare ourselves to others (and why it hurts)

Comparison happens when we're uncertain about our own path. For founders especially, status metrics feel like proof of progress.

Money. Impact. Fame. These become the scoreboard when nothing else feels clear.

Below are some of my reflections on why this work has mattered and a few helpful resources.

Remember, your metrics are not your worth; they’re just numbers on a page, not a measure of your value.

Comparing ourselves often chips away at our founder self-worth, a topic I’ve delved into deeply.

How comparison holds us back

Comparison is the thief of joy. – Theodore Roosevelt

There were countless days as a founder where I would find myself plotting along satisfied with my work, my day, my life, and then one TechCrunch article about a monster round from some company would grind my day to a halt.

My mind would take off. What are they doing that I am not? (Note the "I" in these moments, never the "we".)

Why am I so bad at this?

Why am I so slow?

Maybe we need a better CEO who can make this thing work.

Fuck this, I don't want to work anymore today.

No matter how successful my startup was going at the time—and we had some wonderful years in there—I still found comparisons difficult.

We compare our full lives to someone else's highlight reel. The TechCrunch article doesn't show the sleepless nights or the co-founder fights.

It's easy to mistake your metrics for your worth—to believe that if you're not hitting the same numbers, you're failing.

The hidden costs of comparing yourself to others

When comparison hits, it's physical. Tight chest. Urgency. The urge to doom scroll for more proof that you're behind.

But the real cost runs deeper.

In addition to ruining some of my otherwise joyful days, I have found that going down the road of comparison has a way of eroding my resilience.

Most of us founder types would quickly identify resilience as a key attribute of founders and other startup folks. Startups are full of crazy ups and downs and if you are not resilient, you won't last months let alone years.

So what helps keep us resilient?

If resilience is such a critical and obvious ingredient, it might be worth taking care to protect and foster it.

In my experience, resiliency is best protected by connection and gratitude.

Comparison eats away at both.

I have found that falling prey to comparison destroys my ability to connect with those around me. When lost in my head, I find it impossible to connect meaningfully with my co-founders and teammates. The self-critical voices raging in my mind made it impossible to really hear anything else being said.

These are the same voices that tie self-value to productivity—making it impossible to rest or feel worthy without constant achievement.

Comparison also got in the way of connecting meaningfully with other founders. When I did forge close friendships with other founders, those friendships were life-saving. The dinners and phone conversations I had with close founder-friends on the toughest days of startup life were one of the most powerful contributors to me not throwing in the fucking towel.

But, I know I missed out on a lot of such friendships I might have enjoyed because of comparison. In countless founder dinners, I struggled with the voice raging in my head saying: 'You don't belong here! Everyone else here is more [talented, capable, impressive, etc.] than you are. Just go home."

Comparison can eat away at the opportunity for community right when we need it most.

The hidden cost of anxiety often lurks in these moments, unraveling us silently.

Disconnection from the work that is yours to do

When I compare myself to someone else, I find myself disconnected immediately from my work.

I might read about an exit some company had and think, "I had an idea similar to that! I should have done it. I'm so stupid; I never work on the right things."

I am immediately taken out of the questions and the knowledge that matters most.

In my own life right now, those questions go something like:

• What is the work at hand that is uniquely mine to do?
• How do I want to spend these hours, days, and weeks of my life?
• How can I, Matt, be most helpful to this world right now?

When I get caught in comparison, I lose sight of what I know: there is work here that is uniquely mine to do. In my life right now, that work is coaching: the opportunity to come alongside leaders and founders in the hardest part of their journey.

In your life, there is undoubtedly work that is uniquely yours to do. If you have not found it yet, do not stop looking. If you have found it, protect that knowledge. Do not let the successes of others distract you.

How to stop comparing yourself to others (a practical playbook)

As I shared above, there is no perfect here. But there are a few tools and practices that I have found helpful and which may be of service to you the next time comparison triggers self-loathing for you.

As a starting point, I have found it helpful to sit with the following questions:

• What is my work to do?
• What is enough?
• What drives my happiness?

In the months between selling my last company and beginning to coach, a good friend was visiting from Oakland. He found himself between jobs too, and struggled to determine what might be next. Since we were both in a similar spot, we decided to take some time to explore the questions together.

To make it fun, we headed to the Santa Monica brewery. Because I am a nerd for this kind of thing, we brought along a stack of multi-colored sticky notes and permanent markers. Yes, we brought brainstorming materials to the brewery!

As we sipped our beer, we invited ourselves to imagine what our work might look like in the years ahead. We decided we would brainstorm without constraints, be as crazy as we like.

If you want to try this yourself, here's how:

• Find a safe space (brewery, coffee shop, your living room) with a trusted friend or solo
• Set aside 60-90 minutes without interruption
• Write freely: what kind of work brings you alive? What does "enough" look like financially? What matters beyond the work itself?
• Group your answers into 3-5 major themes
• Keep this somewhere you can return to when comparison pulls you off course

When we had exhausted all the things we could think to dream of, we each bucketed the cards that felt most important into major themes. For me, those themes were:

• Work structure
• Meaning & mission
• Differentiation
• Financial

Getting these goals down on paper helped me to have something to hold opportunities up against in the ensuing months as I explored what might be next for me. The freedom of brainstorming without limits, and in a safe space with a trusted ally, allowed ideas to bubble up that would have otherwise felt too crazy to mention. For example, could I have meaningful, high-impact work, earn a nice living for my family, and work fewer than 50 hours a week? The combination felt crazy.

As I began to try on different kinds of work, I found myself reflecting on that day frequently. And when I finally found my way to coaching, I noticed that the work very much fulfilled each of my major longings I had allowed myself to hold.

I can now look at coaching and very much know that 'yes, this is my work to do' (at least for now!).

Getting to clarity on what my family needs financially (I eventually refined that initial brainstorm a bit...) helped me to answer the question: how much is enough?

Allowing myself to explore the kinds of work that most bring me alive and help me to feel useful to the world helped to ground me in the work that is mine to do.

Putting all of this on paper, first on those sticky notes and later in my journal, gives me a place to return and re-anchor myself when the news of someone else's success pulls me into jealousy and self-criticism.

Know your triggers and set guardrails

Common triggers that pull founders into comparison spirals:

• Social media (LinkedIn fundraise posts, Twitter success threads)
• Industry news sites (TechCrunch, The Information)
• Vanity metrics (ARR, headcount, valuation)
• Certain friendships where comparison always surfaces
• Late-night scrolling when you're already tired

Practical guardrails:

• Limit exposure—mute keywords, unfollow accounts that trigger spirals
• Timebox comparison-prone apps (15 minutes max, not before bed)
• Replace doom scrolling with one grounding action: walk, journal, call a friend

A 5-minute reset when you catch yourself comparing

When comparison hits, try this simple sequence:

1. Pause and breathe. Three deep breaths, eyes closed if possible.
2. Name the story. "I'm telling myself I'm behind. I'm telling myself they have something I don't."
3. Ask: "What's my work today?" Not theirs. Mine.
4. Choose one next action. One email. One call. One paragraph. Just move.
5. Reconnect. Text a friend, step outside, write one line of gratitude.

This isn't about fixing the feeling. It's about not letting it steal the day.

If comparison spirals into anxiety loops that feel impossible to interrupt, this reset can help you come back to the present.

The jealousy unlock

This simple tool cuts through jealousy faster than anything else I've found. My friend Yanda Erlich shared it with me years ago.

Here's how it works:

When you find yourself jealous of someone else's life, you must commit to being jealous of their full life. In other words, ask yourself, 'would I trade every part of my life for every part of the other person's life?'

The wisdom that Yanda's question susses out is that no positive achievement or experience happens in isolation. And no person experiences any part of his or her life as an isolated experience from the rest of his or her life.

The raw materials that made the success I see in another possible may include years of struggle. The life I believe myself to be jealous of may include other parts that are far worse than their counterparts in my own life.

Seen this way, jealousy is a refuting of the full experience of the life that is mine to live and the person that I am meant to be.

For me, that question has been immensely freeing and I find it a powerful antidote right at the moment when I am struggling most.

Jealousy is data

Sometimes jealousy points at something real: a value, a longing, an insecurity you haven't named yet.

When it surfaces, ask:

• What am I actually wanting?
• What does this person represent to me?
• What's one step I can take toward that without trading my whole life?

FAQ: stop comparing yourself to others

Wishing you well

Wherever you find yourself today as you read this post, I wish you well.

Your job is not to win someone else's game. Your job is to do your work.

May you find the work that is yours to do and the life that is yours to live.

Our route out of self-criticism is paved with self-acceptance and self-celebration. If these practices feel awkward and new, you are not alone.

Wishing you all of the acceptance, ease, and connection you dare to desire.

-Matt