Why Your Goal Setting Is Failing: The Art of Strategic Deconstruction
By Sam — Divorced at 34. Rebuilt everything. Here to tell you the second chapter is better. ·
July 2026. The humidity in Portland is doing that weird, sticky thing it does, and Frank—my grumpy, tripod rescue pit mix—is currently snoring at my feet while Lily is in the other room perfecting a masterpiece of construction paper and glitter.
I’ve spent the better part of this week looking at my business projections for the remainder of the year. Four years ago, if you asked me about 'goal setting,' I would have pulled up a color-coded spreadsheet, set a series of SMART goals, and probably cried in a bathroom stall when I didn't hit them exactly how I’d envisioned.
I was a Fortune 500 marketing director then. I was obsessed with the destination. Then, at 34, my life imploded. The divorce happened, the corporate ladder felt like a rickety scaffold in a hurricane, and I realized that I had spent my entire life hitting targets that didn't actually lead anywhere I wanted to go.
If you’re reading this, you’re likely in your own version of a second chapter. Maybe you’re starting over, or maybe you’re just realizing that the blueprint you’ve been following was drawn by someone else. Here is how I set goals now—not to conquer, but to evolve.
Stop Setting Goals for the Person You Used to Be
Most of us fail at goal setting because we’re still trying to impress our younger selves. We set goals based on what we thought 'success' looked like in our twenties. I used to think success was a specific job title and a perfectly curated aesthetic. When I lost the title and the marriage, I had to burn the map.
Before you write down a single objective for the next six months, ask yourself: Is this goal attached to a version of me that still exists? If the answer is no, delete it. Your goals should reflect your current reality—your co-parenting schedule, your energy levels, and the things that actually make you feel alive, not just productive.
The 'Subtraction' Method of Goal Setting
We love adding. 'I want to launch a business, learn Spanish, run a marathon, and volunteer on weekends.' That’s not a goal list; that’s a recipe for burnout.
In my consulting work, I see founders try to scale by adding more features or more hours. It never works. Growth comes from what you stop doing. When I rebuilt my life, I didn't add a million tasks. I removed the noise.
For every goal you set, identify one 'anti-goal.' What are you going to stop doing to make space for this? If you want to launch a side hustle, your anti-goal might be 'no social media scrolling after 8 PM.' If you want to be more present with your kids, your anti-goal might be 'no checking work emails during dinner.' You can’t build a second chapter on top of a first chapter that is already overflowing.
Define the Feeling, Not Just the Metric
Metrics are fine. I like revenue targets as much as the next person. But metrics don't keep you warm at night, and they certainly don't get you through the inevitable 'middle' of a project where everything feels like it’s falling apart.
Instead of just saying, 'I want to reach $X in revenue,' ask yourself how you want to feel while you're doing it. Do you want to feel autonomous? Creative? Connected? When I decided to leave my corporate job, my goal wasn't just to make a living; it was to have the autonomy to pick Lily up from school at 3 PM without feeling like I was asking for permission from a higher power. That feeling was the north star. When the freelancing grind got tough, I didn't quit, because I remembered what the alternative felt like: trapped.
Build in 'Failure Buffers'
If your plan has zero room for error, it’s not a plan—it’s a fantasy. In the corporate world, we pretended failure wasn't an option. In real life, especially when you’re building a new life from scratch, failure is the tuition you pay for wisdom.
I learned this the hard way with Frank. When I adopted him, I thought I could just train him into a perfect companion in a month. He tore up my favorite rug on day two. I had to pivot. Now, when I set a goal, I build in a 20% 'chaos margin.' If I need to finish a project in four weeks, I aim for three. If I need to hit a certain revenue target, I assume a client might flake or a project might go sideways. This isn't pessimism; it’s being an Explorer. You scout the terrain for hazards so you don't get stuck when the path gets muddy.
The Second Chapter Advantage
Setting goals at 38 is fundamentally different than setting them at 24. You have the benefit of experience. You know that you can survive the worst-case scenario because you’ve likely already lived through a version of it.
Don't be afraid to change your goals halfway through the year. The person you are in July is not the person you were in January. Give yourself permission to pivot. Evolution is the only goal that truly matters.
So, what’s one thing you’re going to stop doing this week to clear the path for something better? Head over to the comments and let’s talk about it. I’d love to hear what you’re building.