wean yourself off of external validation

the trick to confidence is actually simple, and it is not "fake it til you make it"

Before we jump in:

1. I was recently on Lenny Rachitsky’s Podcast, talking about how to build teams that can do really hard things. They are calling my conversation “the behavioral psychology playbook for modern managers” !! That feels like a tall order but I hope it is helpful for folks who are trying to manage teams (or simply exist on teams) during times of change or challenge, which I think is especially relevant for everyone these days considering the pace of AI and everything going on in the world.

2. The LAST EVER cohort of my online class, How to Become a Supermanager with AI, starts NEXT WEEK on July 15. I am quickly becoming too pregnant to run more of these, so if you want to learn more about AI fundamentals for managers, building management and coaching tools your team will actually use, and upskilling your team on AI, catch it while you still can. You can get 20% off using the code LASTCHANCE.

3. If you are someone who likes to “voice dump” into ChatGPT and use it to help you sort out your thoughts into something resembling a clear argument or point of view, you may like this Custom GPT I created recently: Wally the Writing Partner. I personally prefer Dictation (voice in → text out) over Advanced Voice Mode (voice in → voice out), and use Wispr Flow as my dictation tool of choice, but there are many options.

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One of the easiest ways to be miserable is to be addicted to external validation. Have you noticed this? It has a way of warping your sense of self and your decision-making capabilities, tricking you into pursuing things that you know won’t make you happy.

The first time I was really struck by this was in business school. I enjoyed and recommend business school, but it self-selects for people who crave external validation and then amplifies that impulse in grotesque ways. I saw deeply smart and thoughtful people become consumed by a desire to secure a job that they knew would only bring them misery and suffering, and then you would talk to them a few years later and they would be like “I can’t believe my career choices have only brought me misery and suffering.” Many such cases.

Then I got to Dropbox, and I saw a different flavor of this, which was The Person Who Was Mad Because Their Friend At Facebook Made More Money Than They Did. And you would say, “OK, if that’s what you care about, why don’t you go work at Facebook?” And they’d say, “oh I couldn’t possibly do that, my friends would judge me for working there.” To which you might say, “Oh, well, good thing you work at Dropbox, nobody really has strong moral opinions about file storage,” but this would not bring them peace, because they had become convinced that their happiness in life was tied to their employer’s market cap, based on nothing.

[I will briefly pause here to recommend anyone contending with the above dynamic reads Joan Didion’s On Self Respect. It’s only four pages!! And will change you!!]

I am not impervious to these lines of thinking. I am less concerned with the prestige of my job, or even my personal wealth, but I do find it triggering when I am talking to someone who seems to think I am an idiot. And as a result I have made choices, often punishing ones, simply to prove to the world that I am up to any challenge, that I am capable enough to solve the more urgent and difficult problems facing whatever organization I find myself in. This is self-defeating in a variety of ways, including that it’s not actually possible, which means I am often setting myself up to fail, and failure is the most effective way to torture me, because, again, I live in fear of looking like an idiot to others.

Anyway. I have put the work in to attempt to disentangle my happiness from my perception of other people’s perception of me. It has helped me, a lot. And I think it will help you too, based on the number of people I see building prisons around themselves, every day laying a new brick cementing their addiction to external validation.

If this is you, here is my advice.

1. Build confidence by getting good at being bad at things

The root of addiction to external validation is a lack of confidence. Confidence is gained in a simple way: repeatedly getting better at things. So if you find yourself making decisions out of a lack of confidence, you need to actively practice getting better at things you are not good at. This is why I love hobbies!

I saw this somewhere, and while it’s a little corny, I do love it as a useful heuristic: when trying something new, you need to do it three times before you can decide if you like it:

1. First time: to overcome the fear of doing it at all

2. Second time: to overcome the skill issue of not being very good at something new

3. Third time: now, you can evaluate whether you actually enjoy the activity, now that neither fear nor still is clouding your judgment.

2. Write down your personal success criteria

When you look back at your life, how will you measure your success? If you don’t define your own success criteria, you'll inevitably default to someone else’s…possibly someone you don’t even respect. Start by identifying your core values, then outline how you'd determine if your actions are aligned with those values. (I made a GPT that will help you with this!)

The idea is not to become overly obsessed with “tracking.” But periodically checking if you're closer to 80% aligned or 20% aligned can help recalibrate your choices away from external validation and towards genuine personal satisfaction.

3. Build a better defense against defensiveness

If you are addicted to external validation, you are likely to become defensive when faced with any kind of criticism. This defensiveness will undermine your growth if you don’t find ways to work through it.

You can give yourself some exposure therapy here by setting up peer feedback conversations where you get more comfortable receiving (and giving!) direct feedback. I have a template for doing those here, with additional tips for getting over your feedback fears. (My favorite tactic is the “two lists” strategy, where you make a list of feedback you think they are wrong about, and one is things that, well, they might be right about.)

I’ve written before about strategies for handling criticism (my “how to take a punch” method). One important nuance, extra relevant here: If someone criticizes you for something that's core to your identity or aligns with your personal success criteria, remind yourself of that. You’re not obligated to demonstrate the opposite of who you fundamentally are. Criticism is only helpful if it helps you uncover blind spots, learn, and grow.

How to take a punch

4. Turn comparisons into curiosity

Comparing yourself to others is probably the hardest habit to break and also the most destructive. You’re not just seeking others’ approval, you’re punishing yourself for someone else’s success! I always found this very frustrating, because not only did it make me feel bad, but then I would be like, “I shouldn’t let this other person make me feel bad.” The result is that I would feel twice as bad. Very cool!! Here’s a toolkit I've developed to manage this:

1. Recognize that nothing undermines happiness faster than comparison. Notice when you feel this happening, not to beat yourself up about it (again….not helpful!) but simply to recognize the impact.

2. Respond with curiosity instead of envy: What does this person value or excel at? Do I actually value that? If I’m not sure, what's a quick experiment I can run to find out? If I am sure, what does this tell me about adjustments I should make to align my life better with my own values?

3. Give it time: The clearer and more validated your own definition of success becomes, the less you’ll care about how you stack up against others.

4. Roast myself, just a little bit, for fun: I am always saying, cheekily, dwelling on other people's success is definitionally loser behavior. Who wants that energy in their life? 😏

As a personal example, there are times I have envied people whose writing has resonated with a large audience, as I’ve toiled away in the depths of Substack. Here’s how I’ve reframed those feelings to be more productive:

This person’s writing resonates with a much larger audience.

• Envy response: They are more successful than I am, which hurts my feelings.

• Curiosity reframing: This person spent years honing their voice and consistently producing work. I respect that work ethic and willingness to put themselves out there. How can I hold myself accountable to consistently publishing work, even if it feels risky?

Someone gets successful by capitalizing on whatever the hot topic of the day is.

• Envy response: This feels shallow or opportunistic, so I will write them off.

• Curiosity reframing: I don’t have a ton of respect for this approach, so it’s not one I want to embrace. But, what can I learn from it? Is it possible I’m swinging too far in the other direction, thinking only about my own self-expression and not enough about how I can be of service to others? I do actually value making things that help people. I’ll try writing on different topics that there is more inherent demand for as an experiment to help me find the right balance for me.

Someone has a unique and clear point of view.

• Envy response: Ugh. I have that, I just never get around to expressing it.

• Curiosity reframing: Clarity, which I deeply value, comes from writing in public, being open to pushback and criticism, and being thoughtful about uncovering blind spots. That process is unpleasant, so I avoid it. How can I be bolder in articulating my ideas to invite more pushback, rather than hedging toward something safer?

Ultimately, the goal isn’t to, like, completely stop caring about others’ opinions of you at all. That…starts to get bad in other ways. But if you want to live a fulfilling life, it is extremely important to recognize when you’re chasing someone else’s definition of success instead of your own. By intentionally building confidence, defining clear personal success criteria, reframing criticism constructively, and transforming envy into curiosity, you can escape the exhausting cycle of trying to win approval from audience that probably only exists in your head anyway. Life becomes simpler, and happier, when the validation you care most about is your own.

xoxo,

hils