You’ve never failed at a habit. The habits failed you. They were built for someone else.
I know that sounds like I’m letting you off the hook. I’m not — you’re absolutely responsible for your life and your choices. But you’ve been given bad advice by an entire industry, and the fix is simpler than anything you’ve tried.
Think about the journal you bought three months ago. Leather cover. Nice paper. You wrote in it for four days. It’s been in the drawer ever since. The vitamins still on the counter — you took them for a few weeks and then your brain just stopped seeing them. The morning routine. The workout plan. The meditation app you used for eleven days.
Every time, the same ending and the same verdict: What is wrong with me?
Nothing. Nothing is wrong with you. The problem is that the entire self-improvement industry gives everyone the same answer — assuming it works for everyone.
Think about how absurd that is outside of self-help. Michael Jordan is rich. You want to be rich. How did he get rich? Basketball. So you go practice basketball — without ever asking: how tall am I? Do I even like this? Am I built for it?
But it goes deeper. Why do you want the money? What’s the actual need underneath — security? Freedom? Because there might be a way to meet that need today — without copying anyone’s path at all.
The differences in how you’re wired on the inside — what drives you, what drains you, how you process the world — are just as real as the physical differences that make copying Jordan’s path absurd. They’re just invisible. To everyone around you and often to yourself.
That’s what the journal was. The morning routine. The vitamins. Someone else’s solution to someone else’s problem, applied to a person it was never designed for.
I ran that cycle for most of my adult life. And I kept concluding the same thing — that I needed more discipline, more grit, more of whatever other people seemed to have. The problem wasn’t effort. It was that I didn’t know myself.
I was diagnosed with ADHD at forty-nine. A previous therapist had suggested it and I’d rejected the idea so strongly that I ended the session on the spot — hung up the phone and never went back. The label felt like a verdict. Something wrong with me.
It took another therapist, months of patient work, to help me see it differently. He didn’t lead with the label. He focused on mechanisms — how my brain actually processes transitions, attention, novelty, emotion. Months later, when the word ADHD finally entered the conversation, it didn’t feel like an accusation but just a word that describes the mechanisms in me I knew were real.
What I’d discovered was that my mind is a race car with no brakes. Fast, intense, wired for speed and novelty and the thrill of building something from nothing — but weak on the things that require steady, boring, repetitive maintenance. Transitions between tasks cost me more than they cost most people. I feel everything at higher volume — excitement, frustration, curiosity, anger. For forty-nine years I’d been blaming the driver. The driver was fine. The car was just built different, and nobody gave me the right manual. No brakes is a limitation — but it’s not a flaw. It’s how the car is built. And I can’t fix it by stomping harder where everyone told me the brake pedal should be.
After my diagnosis, I found the ADHD community. And these people had figured out something that goes way beyond ADHD — something the mainstream self-improvement world still hasn’t caught up to.
They know, from lived experience, that people can be wired radically differently on the inside while looking roughly the same on the outside. You watch other people handle things that are hard for you, and you conclude you’re falling short. You don’t realize the game is different for you. You just think you’re losing.
The mantra I kept hearing was: don’t try harder, try different.
That phrase broke something open for me. It gave me permission to stop fighting myself — to stop concluding that I just needed more discipline, more willpower, more of whatever everyone else seemed to have.
But “try different” is a door, not a destination. Different how? I started experimenting. And somewhere in the experimentation, I noticed a pattern: the things that stuck were the things I actually enjoyed. Not because I was being lazy — because enjoyment turned out to be a reliable signal that something fit.
So I started asking a question that felt almost transgressive:
How can I make this more enjoyable?
Sometimes that means easier. Sometimes more comfortable. Sometimes just — something you actually want to do, for whatever reason. Because it’s meaningful. Because it’s energizing. Because it’s calming. Because you don’t have to convince yourself.
You don’t get to choose what those things are. You get to discover them. You won’t know what works until you experiment. The answers will reveal things about you. What you need. What drains you. What makes you come alive. The experiment is the point.
I’d had trouble choosing to go to sleep my entire adult life. Forty-plus years of staying up until two or three in the morning. I’d tried everything “try harder” offers. Earlier alarms, thinking longer days would make me so exhausted I’d just collapse. No screens. Willpower. Guilt. Or maybe I was a night owl — just wired that way. Or I spent so much time doing what I “should” do during the day, I wanted to just rebel a bit and claim time for myself. All partially true. None of them the real issue.
The real issue wasn’t discipline. It was that going to bed requires a transition — and my brain doesn’t do those. Remember the race car? Mine doesn’t stop. Whatever I’m doing in the evening — reading, watching something, lost in a project — that’s the highway, and my brain is cruising. Without the brakes other people seem to have, I can’t just decide to stop and make a hard-right turn toward sleep. I need an off-ramp — one that’s as satisfying as the stretch I’m on, that allows a new direction without fighting the momentum.
That’s my wiring — yours will be different. But the principle is the same: I had to learn what my car actually needed instead of stomping where the brake pedal should be.
For forty-plus years, I didn’t understand any of this. I just thought I was failing — not putting future-Ben ahead of present-Ben. A lack of discipline. A willpower problem. I was working against my wiring without knowing it, and blaming myself for the results.
So I stopped asking “how do I force myself to go to bed?” and started asking “how can I make the off-ramp more enjoyable than the highway?”
I redesigned the whole experience.
At 9:30, I’d take some magnesium and melatonin. I’d resisted supplements for years — one more chore. But I added lemon balm extract to the ritual, which actually tastes good, and suddenly I looked forward to it. A small enjoyment that also started a clock: I knew the magnesium and melatonin would pull me toward sleep within an hour. No resistance, just a first step with momentum already built in. I upgraded my bedroom: nice nightstand, good light, sheets I wanted to climb into. Made the room a place I’d want to be, not just a place I was supposed to go. Then I added the real pull: sleeping earbuds, an audiobook I was really into, thirty-minute timer — and a commitment to be in bed by eleven doing this thing that actually sounded fun. And a deal with myself — if I’m still awake after thirty minutes, I can go back downstairs.
I never once went back downstairs. It worked the first night. Asleep within fifteen minutes. I kept restarting chapter one because I could never stay conscious long enough to finish it. And it never stopped working — I’d believed my whole life I was a night person. Turns out I’d just never had a reason to go to bed. How incredible is that? 40+ years of doing things one way (a “bad habit”) changed permanently in one day. I was never the problem — I just didn’t have the right solution.
And here’s what nobody told me about getting this right: when you fix one thing by designing around how you actually work, the energy you were wasting on that fight goes somewhere else. I had more patience with my kids. More focus during the day. More capacity for the people I love. All the energy I’d been burning just to get through the night — it didn’t disappear. It went into my actual life.
After the bedtime experiment worked, I got curious. What else could I apply this to?
I started with my workday. What would make it more enjoyable — not in some abstract future, but right now, today? The answers felt almost embarrassingly small. A wool rug under my bare feet while I work. A mini fridge within arm’s reach. Incense. My favorite socks every single day.
I’d been told my whole life that the key to sticking with something was a strong enough “why.” Visualize the results. Imagine how healthy you’ll be in two years, how good you’ll look, how good you’ll feel. And when it didn’t stick, the verdict was always the same: you must not want it bad enough.
Turns out that was wrong.
A study out of Imperial College London tested what actually makes habits stick — not just repetition, but what accelerates the process. Their finding: when people found a behavior enjoyable, each repetition strengthened the habit more. But here’s what jumped out at me — knowing something was good for you didn’t predict whether it stuck. Enjoyment did. Utility didn’t.
I wanted it. I just didn’t enjoy the process. And no amount of “why” can overcome a “how” that drains you — at least in the long run. The research says that’s the wrong lever entirely.
Here’s where something in you is going to push back. Not on the logic — on the feeling.
Giving yourself permission to pursue what is enjoyable feels wrong. A responsible adult shouldn’t need a nice rug to get their work done. They shouldn’t need to fill their day with things they enjoy. And if they do, they’ll fall into the temptation of just eating donuts and binging on Netflix all day — because we all have to do work we don’t want to do. That’s the reality of life.
That flinch is the old program running.
We treat enjoyment like it’s a reward you earn after doing all the hard things — or worse, like a weakness to manage. We maximize suffering and suppress enjoyment, and we call that discipline. We assume that if something feels good, it must be taking away from something more important. That enjoying your commute means you’re not serious about your job. That making hard phone calls from a massage chair somehow cheapens the work — when in reality, the work gets better because you’re not fighting yourself while you do it.
Besides, your life isn’t what you accomplish. Your life is what you experience. Day by day. Moment by moment. The only version of your life you’ll ever have is the one you actually live through — and when you fill those moments with enjoyment, you’re not avoiding life. You’re living it.
I want to be precise about what I mean by enjoyment — because the word can sound soft. There’s surface enjoyment — or maybe pleasure is a better word: the socks, the sheets, the right playlist while you work. The things that reduce friction and make moments feel good. And then there’s something deeper — the satisfaction of doing a thing that fits who you actually are. Using your wiring the way it was built to be used.
Jordan didn’t grind through basketball despite hating it. He ground through it because something deep in him loved the process — the competition, the pursuit, the work of getting better. That wasn’t discipline overriding desire. That was desire driving discipline.
Enjoyment (even pleasure) isn’t the opposite of meaning. It’s the fuel for it. The surface enjoyments clear the path to the deeper ones. You’re not going to discover your version of basketball if every step of the search feels like punishment.
The experience of your life is your life. Load it up.
Once I saw the principle, I couldn’t unsee it. I started asking the question — “How can I make this more enjoyable?” — about everything. And it kept working.
The shower got lavender scent and a sugar scrub. My keys land in a little hippo with its mouth open, because that’s more fun than a hook. I thought I needed a whole new career — midlife crisis stuff. Like a boat captain who wants a different boat — but this is the one I have, and I’m already out on the water. Burning it down wasn’t feasible or smart, at least not today. The career is valuable to my family. It’s real. So the question became: given that this is what I’m working with, how can I make it more enjoyable?
I brought plants into my office. Changed my desk so I faced the window instead of the wall — I’d had it backwards for years, optimizing the Zoom background instead of my own experience. Started making one small improvement each day — delegate one task, fix one process. No vision board. No five-year plan. Just making micro-improvements to anything I could that would increase my enjoyment in any way.
Within a year, I hadn’t necessarily accomplished more in any business sense. But I was happier with my life — my experience of the day — than I’d been in a very long time. In some ways, ever. Life didn’t feel like a fight with myself anymore. I wasn’t managing myself with a whip. I was finding freedom to be me, and it was working better in the ways that actually mattered.
In every case, the same thing happened: something that had required enormous willpower became easy once I designed for enjoyment instead of discipline. The resistance was never about character. It was about fit.
Remember the habits I mentioned at the start of this article? The ones I’d “failed” at? They stuck — with zero effort — the moment I found my version. No three-week habit-forming runway. Just thinking of the idea and trying it.
The journal? I write articles about ideas I’m learning. I failed at journaling for decades because I was writing reports about my day. Turns out I was a writer the whole time — just not that kind. The vitamins? On the counter where I can see them. Every morning with my tea. The meditation app? I have a thinking chair. I sit down and think about whatever I feel like thinking about. None of it is willpower. A hundred percent of it was being curious and willing to experiment.
When something doesn’t work? Throw it away and try something else. That’s the beauty of it — you’re not committing to a system. You’re running experiments. The feedback is immediate. You don’t need three weeks to build a habit. You need one day to know if this version fits.
There’s a version of “try harder” that’s much more dangerous than failing at a morning routine. It’s succeeding at the wrong thing. I spent years building things I was good at but didn’t care about — and the better I got, the more trapped I felt. The career built for someone else’s approval. The discipline framework you adopted because you were supposed to. You pushed through anyway, and even when it works — even when you arrive — you’re full of resentment. External success, internal betrayal. The compass you followed was never your own.
A life that’s working is full of hard things. The boxer gets hit in the face. The activist risks everything. But they’re not forcing themselves — something deeper drives them, and it’s as natural as breathing. That’s the right hard thing. A fight you chose. It doesn’t need a motivational poster. It needs you to get out of the way.
The question isn’t whether life will be hard. It’s whether the hard thing is yours.
Enjoyment doesn’t mean ease. It means aliveness — the feeling that what you’re doing matters to you, even when it costs you something.
There’s a difference between the discomfort of growth and the exhaustion of misfit. Growth stretches you — it’s hard, but it leaves you proud. Misfit drains you — it’s hard, and it leaves you resentful. One is the burn of becoming. The other is the slow bleed of forcing yourself into the wrong shape.
And here’s what shifts when you make that the metric: the outcomes start to matter less. Not because you stop caring — but because your sense of wellbeing isn’t chained to them anymore. Maybe you run a smaller business instead of a larger one. Maybe you choose a career that’s less prestigious but actually fits. When how you experience yourself moving through your day becomes the compass, your happiness isn’t tied to some future arrival. The outcome isn’t outside or ahead of you. It’s inside and now. And that’s the only life you actually have.
Did you enjoy today more than yesterday?
Not from the outside — not did you check the boxes, hit the targets, complete the routine. From the inside. Was today more satisfying? More yours?
My grandpa used to say: “If it ain’t fun, don’t do it.” He wasn’t lazy. He worked hard, raised a family, built a life. He just refused to spend it grinding through things that made him miserable. He had one of the best lives I’ve ever seen.
Here’s what the old approach never tells you: when suffering is the assumed cost, you have no feedback. You could gut it out for twenty years and never know if you’re on the wrong path — because misery is expected, so misery proves nothing. But when the metric is enjoyment, you get data now.
And in the hard moments — grief, heartache, real pain — the question shifts. You’re not asking “how do I make this more enjoyable?” You’re asking “how do I make this more bearable?” You’re going to suffer, but why make it harder than it has to be? Same compass. Different phrasing. You’re still the one navigating.
The days I enjoy most are the days that feel like mine — where what I love is woven into how I live instead of pushed to the margins.
If this sounds selfish, or like a recipe for disaster — I understand. We’ve been taught not to trust ourselves. We assume that without some slave-driver part of us forcing us to do things we don’t want to do, we’ll discover we’re lazy monsters underneath.
I’m willing to bet you’re better than you give yourself credit for. When you give yourself permission to pursue what you enjoy, you’ll find that what you actually want are the good things — and getting them is easier when you stop fighting yourself.
You don’t need a vision board. You don’t need someone else’s morning routine. You need tomorrow to feel slightly more like yours than today did.
And the question that gets you there isn’t “how do I try harder?”
It’s: what isn’t working for me — and how can I make it more enjoyable?
Your answers will be different from mine. That’s the whole point.
Your life isn’t ahead of you. It’s not waiting at the end of some plan. It’s happening right now — inside, today. And you can make it better this afternoon.
I found this both interesting and informative. Thank you for sharing, Benjamin.
Freaking loved this. The difference between repetition and enjoyment is everything. 🙌