Why Your Goal Setting Is Failing (And How to Actually Fix It)
By Dante — Emotionally available. Yes, we exist. No, I won't explain your ex to you. Okay fine, I will. ·
The 'New Year' Fallacy in September
Most people think January is the time for a reset. Honestly? That’s a trap. By the time January rolls around, we’re all burnt out from the holidays, shivering in the Chicago wind, and trying to force ourselves into a version of our lives that doesn't actually fit. September is the real pivot point. It’s the 'back to school' energy that never really leaves your nervous system, even if you’ve been out of school for a decade. It’s quiet, the air is crisp, and it’s the perfect time to look at what you’re doing and ask yourself why.
I spent a lot of my twenties setting goals like a video game quest—level up the career, level up the social life, level up the apartment. I hit a lot of those marks, and yet, I found myself sitting in my therapy sessions at 28, wondering why I felt like I was running on a treadmill that someone else had turned up to speed ten. I was achieving, but I wasn't arriving.
Goal setting isn't about productivity; it’s about alignment. If your goals feel like an obligation, you’re already behind. Let’s talk about how to stop setting goals that look good on paper but feel like lead in your stomach.
Stop Tracking Outcomes, Start Tracking Inputs
In UX design, we obsess over the user journey. If the user isn't doing what we want, we don't blame the user—we look at the friction in the design. We look at the process. Most of us treat our personal goals like a final output: 'I want a promotion,' or 'I want to run a marathon.'
Those are outcomes. You have limited control over outcomes. You can train for the marathon and get the flu, or you can crush your quarterly goals and find out the company is doing a hiring freeze. When your goal is tied entirely to the outcome, you set yourself up for a identity crisis every time reality happens.
Instead, I want you to start tracking inputs. If you want to write a book, don't set a goal to 'get published.' Set a goal to write 250 words every Tuesday and Thursday morning. If you want a better relationship, don't set a goal to 'be happier.' Set a goal to have one undistracted conversation with your partner every night for fifteen minutes. Inputs are the only thing you actually control. If you focus on the inputs, the outcome usually takes care of itself. And if it doesn't? Well, you’ve built a habit that actually matters.
The 'Five-Year' Lie
We love the 'Five-Year Plan.' It feels safe. It feels like we have a map. But I’m 33, and if I look back at where I thought I’d be at 33 when I was 28, I’d be wrong on almost every count. And thank god for that. If I’d stayed on the path I planned at 28, I’d probably still be in a relationship that wasn't working and working a job that didn't challenge me.
Life is a series of emergent properties. You don't know what you want until you start doing the work. You don't know if you’ll like that new career path until you’ve actually sat in the chair for three months.
My advice? Lower your horizon. Stop trying to plan five years out. Plan for the next ninety days. Ninety days is long enough to see real progress, but short enough that you don't lose touch with the reality of who you are right now. Every quarter, sit down with a drink you like, a notebook, and zero expectations. Ask: What do I want to be better at in ninety days? Then, define the inputs for that specific sprint.
Embracing the 'Messy Middle'
There’s a point in every goal-setting cycle where the novelty wears off. You’ve stopped getting the dopamine hit from the 'start,' and you aren't yet at the 'finish.' This is the messy middle. This is where most people quit.
In therapy, we talk about 'emotional regulation.' It sounds fancy, but it just means learning how to sit with discomfort without immediately trying to change it. When you’re in the messy middle of a goal, you’re going to feel bored, frustrated, or like you aren't moving fast enough. Your brain will tell you that the goal was wrong, or that you aren't cut out for it. That is a lie. That is just your brain wanting to return to the comfort of the status quo.
When you hit that wall, don't re-evaluate the goal. Re-evaluate your input. Are you doing the work? If yes, keep going. If no, be honest about why. Is it fear of success? Fear of failure? Or are you just tired? Being tired is fine. Rest, then get back to the input. But don't abandon the ship just because the ocean got a little choppy.
Radical Honesty with Yourself
Before you write down a single goal for this autumn, I want you to ask yourself one question: Am I doing this for me, or am I doing this to prove something to someone else?
We all have that internal voice—maybe it’s an ex, maybe it’s a parent, maybe it’s that one coworker who thinks they’re smarter than you—that we’re constantly trying to appease. If your goal is to 'get in the best shape of my life,' but the subtext is 'so my ex sees my Instagram and regrets everything,' you’re going to fail. Not because you aren't capable, but because you’re fueled by resentment, and resentment is a terrible long-term energy source.
Set goals that make your own life easier, quieter, or more interesting. Everything else is just noise.
Anyway, I’ve got a backlog of tickets to clear before the weekend hits. If you’re staring at your list of goals and they’re starting to feel like a cage instead of a map, shoot me a message. We can look at where the friction is. I’m usually around.