Around 15 years ago I had the idea to create a membership site that would teach non tech savvy and busy people to generate a side income of $1,000 per month online in their spare time.
I worked relentlessly for months on this project. I remember creating more than 250 screencast videos, articles and courses about the various methods. It was huge, far more than the project needed for an initial launch.
But each time I'd set a launch date, I'd always bend myself into a pretzel trying to justify why the course isn't good enough and more content needed to be added. I'd push the date back a week, instantly feel relief, and get back to work on the course content. I call this scope creep.
After months of delaying, it was only when a close friend of mine called me out on my bullshit that I finally launched the course. Pulling the trigger was the most painful thing I'd ever done; I was convinced it was going to fail and amount to nothing. Yet, we actually ended up doing 100 sales in the first day - far more than I ever expected.
I didn't realize it at the time, but "perfectionism" was a thinly disguised veil for what was really going on under the surface - fear of failure.
The Perfectionism Trap
Perfectionism can often masquerade as a positive trait - it looks like having high standards, a strong work ethic, or a sharp eye for detail. At first glance, it might even seem admirable. But beneath the surface, perfectionism can be a subtle yet powerful form of procrastination - a clever disguise for avoidance.
Instead of helping us move forward, perfectionism can actually paralyze progress. It’s not really about doing your best rather about avoiding the discomfort of imperfection, criticism, or failure. It’s fear wrapped in the illusion of productivity.
That's what was happening to me without even realizing it. I kept delaying the project because, in my mind, the project would inevitably fail and it was easier to delay the launch than face up to reality.
What we believe to be true drives everything - our thoughts and actions all come from our beliefs, whether true or false.
Imagine you're tasked with writing a proposal for a new client. Instead of getting started right away, you spend hours choosing the perfect font, agonizing over every sentence, and endlessly rewriting the introduction - not because the work demands it, but because you’re afraid it won’t be “just right.” Days go by, and the actual content of the proposal still isn’t finished. You tell yourself you’re being thorough, but in reality, you're stalling - using perfectionism as a shield to delay delivering something that might be judged.
This kind of delay isn’t due to laziness or lack of motivation. It’s fear-driven procrastination in disguise.
What's Really Going on?
The first step with procrastination is always awareness: what's really causing you to delay what you know you should be doing?
Here's what procrastination due to perfectionism looks like on the surface:-
- Waiting to record a video until you have the “perfect lighting, script, and equipment.”
- Putting off replying to messages because you want to word your response “just right.”
- Not delegating a task because you fear someone else won’t do it “as perfectly as you would.”
- Avoiding starting a project because you feel you’re not yet skilled enough to do it flawlessly.
- Holding off on launching a project because you haven’t “fine-tuned every detail.”
- And so on...
Be honest with yourself - why are you really delaying?
What you're looking for are those little rebuttals in your head that pop up when you think about doing something. They can often go completely unnoticed but they hold the keys to the castle.
Common reasons can be:-
- Fear of judgment - I'm worried what people will think of me. What will the backlash be? Will I be cancelled? Will my friends think I'm a joke?
- Fear of failure - I'm scared the whole project will fail, it will be a waste of time, I won't be able to pay the bills, I'll have to go back to work etc.
- Fear of not being enough - I'm not good enough, I'm not qualified, I'm not ready, my work is not good enough.
While these represent broad categories, fears are often extremely subjective and nuanced.
Tactics to Battle Perfectionism
I refer to tactics as things that you can try to "brute force" your way through an unhelpful pattern. Tactics don't do anything to change or address the underlying causes, but they can be useful tools and frames in the moment to get you over the line. Some of these tactics are practical while some are more mental frames or models that help you look at the situation through a new lens enough to take action.
Fear of Judgment
- Feel the fear and do it anyway. What kind of person are you? Set your goal to be someone that you admire. Identity based goals are extremely powerful and can transform fears into rites of passage. Everyone that you look up to has faced fears and they've overcome them to succeed. Build an identity that leans into fear just like those people that you admire.
- Be happy with your intentions - Most judgment isn’t really about you - it’s about the other person’s perspective, values, or insecurities. What people think or say reflects their own lens, not your worth. Are you happy with what you're doing? If yes, then that's what matters. It's easier said than done, but turning inwards as opposed to outwards can help alleviate fears. Practice validating yourself instead of relying on external approval. Acknowledge your own effort, courage, and progress - even if no one else claps.
- If you're not pissing someone off, you probably aren't doing anything important - If you try to keep everyone happy, you’ll water yourself down into irrelevance. Making an impact means disrupting comfort zones - your own and others’. It means challenging the status quo, questioning norms, speaking honestly, and taking a stand for something that matters. Not everyone will clap. Some people will feel uncomfortable. Some will disagree. Some will be annoyed, offended, or critical. That’s not a sign you’re doing something wrong - it’s a sign you’re doing something real
- Nobody cares about you - If you really knew how little time people spend thinking about you, you’d stop holding yourself back. Most of the fear of judgment is rooted in the illusion that everyone’s watching, analyzing, or critiquing us. But the truth is that people are usually far too busy thinking about themselves. Their own problems, their own insecurities, their own to-do lists.
- You'll be dead soon ("memento mori") - The clock is ticking, and you don’t get to know how many ticks are left. So why waste another precious minute obsessing over whether something is perfect? Perfection is a moving target, and chasing it only steals time you’ll never get back. What matters is that you do the thing, finish the project, share your ideas - flawed, human, and real. Because in the end, no one will remember how polished your work was; they’ll remember that you had the courage to put it out there. Let your mortality remind you: it’s better to leave behind something imperfect than nothing at all.
- Learn from the dying - In Bronnie Ware's book "The top five regrets of the dying" she listed "I wish I’d had the courage to live a life true to myself, not the life others expected of me" as the first common regret. This regret cuts deep because it speaks to unlived potential - dreams deferred, passions suppressed, and choices made for the sake of approval rather than authenticity. Many people spend much of their lives trying to meet the expectations of parents, partners, employers, society… and only at the end do they realize they never truly honored what they wanted.
Fear of Failure
- Redefine failure - It's likely that you're currently defining failure as outward signs of success; a closed sale, a growing business or a speech that goes down well with the crowd. These external signs of validation don't often reflect the courage, hard work and emotional labor that you've demonstrated to show up and are often subject to variables that are outside of your control.
One strong way to reframe a fear of failure is to become clear on what traits a successful person has and embody them. In essence, this is an exercise of defining your personal values. Of the people that you admire, what behaviors do they do? What do you admire about them? How do they live their life? Use these insights to create your own list of personal values that you aspire to live by. This internal driven approach to living means that a so-called failed project can feel like a success because you shipped in line with your values. Focusing inwards can remove the pressure at that critical moment when you're otherwise frozen with fear. - Focus on the process vs the outcome - when you obsess over the final result - how good it will be, how it will be judged, whether it will meet some impossible standard - you paralyze yourself before you even begin. But when you bring your attention back to simply doing the work, one step at a time, the pressure eases. The process becomes about showing up, building moment, experimenting, and learning - not proving your worth or producing a masterpiece. Ironically, the best outcomes often come when you stop fixating on them and instead immerse yourself fully in the act of creating.
- What's the worst the could happen? - Tim Ferriss uses a powerful technique called "fear-setting" to overcome his fear of failure - a form of journaling where he systematically explores the worst-case scenarios. Instead of letting vague anxiety control him, he writes down exactly what he's afraid might happen, how likely it really is, what he could do to prevent it, and how he could recover if it did. By shining a light on those fears, he often realizes they’re far less catastrophic than they feel in his head. This process helps him separate real risks from imagined ones and gives him clarity and confidence to move forward. As Ferriss puts it, “Define your fears instead of your goals.” Because once you see that even your worst-case scenarios are often survivable - or even reversible - they lose their power to paralyze you.
- Normalize failure - Every expert was once a beginner who stumbled, and every success story is built on a foundation of imperfect attempts. Failure isn’t a verdict - it’s feedback. The more you normalize it, the more freedom you give yourself to take action, experiment, and learn without being paralyzed by the need to get everything right on the first try.
- Lower the diving board - Perfectionists often set enormous, all-or-nothing goals. Break them down into smaller, low-pressure tasks. Reduce the emotional weight of each step so it’s easier to just get started and stay in motion.
Fear of Not Being Enough
- Progress over perfection - Shift your internal target from “perfect” to “progress.” Create a new success metric: Did I move forward today? Even a tiny step counts. Let forward motion become your new measure of worth - not flawless outcomes.
- Get comfortable being seen imperfectly - Practice gentle exposure therapy: share something before it’s fully “ready.” A rough draft. An early idea. A low-stakes post. The goal is to desensitize yourself to being seen while still in progress—and realize you’re still enough, even then.
- Connect Your Work to Meaning, Not Validation - Refocus your motivation: Why does this matter to me? When you shift from “Will this be good enough?” to “What impact could this make?”, it becomes less about self-worth and more about contribution.
My 6 Months of Perfect Days
Despite being a chronic procrastinator, a few years ago I managed to string together 6 months where I completely my habits every single day without fail.
Amongst others, these habits included:-
- Meditation
- Daily journaling
- 2 hours of deep work
- Daily reading
- Gym (at least 3x per week)
I had never been so productive in my life. The experience taught me a few key points about procrastination:-
- Resistance never fully goes away
- You don't overcome procrastination through some grand "aha moment" or epiphany. Ideas alone aren't enough.
- Emotional fitness is the best way to deal with procrastination
During those six months I developed habits of the mind that repeatedly overcame the lower motivational pulls. When I craved for a dessert or didn't want to work out, I was emotionally strong enough to feel the resistance or the pull and do what I needed to do anyway.
What was my main way of doing this?
Turning inwards
You may have noticed that a lot of the tactics listed above are about focusing inwards on your beliefs, your values and what you feel is right to do.
By defining a set of core values or rules that you live your life by, it becomes easier to notice thought patterns and use habits of the mind so that you're not at the mercy of your lower emotions.
If I noticed that I was scared to publish a video then I'd turn inwards and ask myself if publishing the video is in line with the kind of person I aspire to be?
Do I aspire to be someone who caves in to fear or someone that feels the fear and does it anyway?
By habitually thinking along these lines as opposed to ruminating in my lower emotions, I could reliably bring myself to overcome my fears and continually execute.
The Good News and the Bad News
The bad news is you can't solve your procrastination once and for all with a new idea or technique so that it never occurs again.
The good news is that you can learn habits of the mind to reliably and consistently notice and manage your lower emotions so that they no longer hold you back from realizing your true potential. It's like going to the gym - you can have your dream body but you have to regularly work out for it.
The next time you're procrastinating on something, become aware of that little voice in your head and instead of ruminating in fear, use some of the techniques described above to turn inwards and live in line with core values.
While writing this blog post, I came across this post about fear of failure from Nick Wignall and loved it. We have similar views on procrastination but he does a much better job of explaining it - definitely give it a read.