You Can’t Optimize Your Way Out of the Wrong Strategy
When you're heads-down on the wrong premise, trying to optimize your way to success is just a more efficient way to stay buried.
→ This is a story about what happens when you finally stop tweaking and start telling the truth.
TL;DR
The Academy keeps optimizing the same show. I spent months doing the same thing with my business. This piece is about what finally changed — and why the right foundation matters more than a better execution of the wrong premise. Heads up: This post runs a bit longer than most — you’ll need about 8-minutes. Please grab a coffee, your journal, and hang with me for a bit.
The Oscars Are Still at It
I turned on the Oscars Sunday night. I lasted maybe forty-five minutes.
It wasn’t bad, exactly. It was just… the same. The same format, the same pacing, the same sense that somewhere in a conference room, a group of very smart people had spent months figuring out how to make this year’s show run a bit better than last year’s. Shorter. Snappier. More produced.
And, in the end, we got the same show.
The Academy has been trying to ‘fix’ the Oscars for years. They’ve adjusted the runtime. They’ve added more nominees and new categories. They’ve hired different hosts, tried no host, changed up how the nominees are announced, experimented with opening numbers, and even the in memoriam timing. Every year there’s a tweak. Every year the ratings tell the same story – less people are watching.
Last Sunday’s ceremony drew around 18 million viewers (a 9% decline from 2025) — respectable by recent standards, but a fraction of the 57 million who tuned in at the show’s peak in 1998.
To be fair, the Oscars are fighting more than a format problem. Streaming has fragmented how we watch. Movie-going isn’t the cultural ritual it once was. Celebrity, for a lot of people, just doesn’t land the same way anymore. These are real headwinds. But the response to all of them has been the same: trim the runtime, shuffle the segments, and hope that a tighter show fixes a deeper disconnect. It hasn’t. And I don’t think it ever will.
Here’s the thing: the Oscars aren’t failing because they’re executing poorly. They’re failing because they keep asking ‘how do we do this better’ when the more honest question — the scarier one — is ‘how should we be doing this?’
Meet The Innovator’s Dilemma (A Small Detour)
There’s a business concept that I keep coming back to when I think about this: The Innovator’s Dilemma. It’s from a book written by Clayton Christensen in 1997 that is a business leadership staple. The core idea translates pretty cleanly to what’s happening on that Oscars stage every March.
The argument, roughly, is this:
Successful organizations tend to get trapped by their own success. They keep refining what’s already working — making it more efficient, more polished, more optimized — while they ignore everything else.
Not because they’re stupid or lazy. Because improving what exists feels responsible. It’s measurable. It looks like effort. It is effort.
The problem is that optimization and reinvention are not the same thing. One improves the existing answer. The other asks whether you’re still solving the right problem.
Christensen was talking about Kodak and disk drives and steel mills. The trap, it turns out, scales. And the Academy, well, they’ve been rearranging deck chairs on the Titanic for a long time.
The most seductive thing about optimization is that it always feels like progress. But if the underlying premise is off, you can optimize forever and still end up exactly where you started.
I know this because I did it.
I Was Doing the Same Thing
I had to get honest with myself about something uncomfortable over the holiday’s last year: my business wasn’t going anywhere.
Nothing was broken in an obvious way. I was doing the work, showing up, iterating — tweaking my messaging here, adjusting an offer there, refining how I talked about what I did.
From the outside it probably looked like momentum. From the inside it felt like walking through wet cement.
The hard part wasn’t admitting that things weren’t working. It was admitting why.
Here is my (almost 3 months removed) assessment: I was so committed to what I thought I wanted to build that I had blinders on. I had invested time, energy, and a lot of identity into a particular vision of my business, so instead of asking whether the vision still fit, I just kept trying to make it better. Tighter. More refined. More presentable.
I wasn’t executing badly. I was executing diligently on the wrong premise. And the more I optimized, the more entrenched I got — until the question I actually needed to ask, the one the Academy still doesn’t seem to have discovered, got buried under all that effort.
Should I even be doing this? Or is there something else that will fit better?
It took me longer than I’d like to admit to stop and ask it.
The Three Questions That Changed Everything
When I finally stopped, I didn’t hire a consultant or buy a course or build a spreadsheet. In fact, I put all of those things away, got quiet, and started pulling on threads.
I was reading. Listening to podcasts. Working through exercises and reflections that had been sitting on my to-do list for months. Things were simmering — ideas, instincts, questions I didn’t quite know how to organize yet. I didn’t have a plan. I just kept going, letting things percolate, until slowly, almost without realizing it, the dots started to connect.
What emerged were three questions:
What am I actually great at?
What do I love doing?
What do I want to stand for?
They sound simple enough. They’re not. Because answering them honestly — not the aspirational version, not the version that looks good in a bio — requires you to set aside what you think the market wants, what your peers are doing, and what you’ve already invested in. It requires you to be a little ruthless about the gap between who you’ve been performing as and who you actually are.
I’d done values work before. I’d thought about strengths. I’ve known what I love to do for a long time. But, I’d never sat with all three questions at once and looked where they pointed.
What I found surprised me. Not because it was completely new, but because it was so clearly and obviously a convergence of my unique skills and interests. The vision I needed had been there the whole time. I’d just been building around it instead of from it.
And here’s where things gets practical, because this isn’t just a personal growth story. That foundation became my brand strategy for this year. Which shaped how I repositioned this Substack. Which informed the offers I’m building. Not in a forced, reverse-engineered way, but in the way that things flow naturally when the foundation is actually solid.
That’s what your brand is supposed to do. Not decorate your business. Not make it look more polished. Ground it. Filter it. Give you a clear basis for every decision that comes after.
The Academy keeps redressing the Oscars set. I knocked the set down and rebuilt my business from the foundation. The difference isn’t cosmetic — it’s everything.
I like to include what I call Purpose Plays in my posts. You should think of them as brief breaks in the story for you to reflect on how the themes being presented align (or not) with what you’re actually building. Are you ready for a little honest reflection?
Purpose Play
Think about the thing in your business that you keep trying to fix. The offer you’ve rewritten three times. The messaging that never quite lands. The strategy you’re still refining six months later.
Now, sit with these three questions for a few minutes. Not the polished answers. The honest ones.
What am I actually great at — not just competent at, but genuinely, distinctively great at?
What do I love doing — the work that doesn’t feel like work, even when it’s hard?
What do I actually stand for — the values that show up whether I’m being strategic about them or not?
Where do those three things point? That’s not just self-reflection. That’s your truth. And if what you’re currently building doesn’t live inside that intersection, it might be worth asking why.
You don’t have to burn anything down today. But you do have to be willing to look.
This is What Brand Actually Does
Here’s what I want to leave you with.
Brand gets talked about like it’s a layer you add — the colors, the fonts, the tagline, the aesthetic. And yes, those things matter. But they’re downstream of something more fundamental. Brand, at its best, is the thing that tells you what belongs and what doesn’t. It’s not a wrapper you put around your business. It’s the filter your business runs through. (For those of you paying attention, yes, I’m referencing the title of one of my other posts.)
When brand is built from the right foundation — from an honest answer to those three questions — it stops being something you maintain and starts being something that works for you. Decisions get easier. Offers get clearer. The work starts to feel like yours again.
That’s what I found on the other side of my reset. Not a perfect business. Not overnight success. But a clarity that makes every next decision easier than the one before it. Because I finally have a foundation that actually fits.
The Oscars will probably keep moving deck chairs around next year. And maybe it’ll help a little. But until someone in the room is willing to ask the real question — not ‘how do we do this better’ but ‘who is this actually for and does this format still serve them’ — they’ll keep getting the same answer.
The real work isn’t making the wrong thing better. It’s having the courage to let it go and build the right thing instead.
About the Work
I’m Amy Zwagerman—brand strategist, fractional CMO, and founder of The Launch Box. I work with founders and marketing leaders to translate durable marketing principles into strategies and systems that fit their specific context, stage, and goals.
Marketing Jam sits alongside my client work as a place to explore ideas more openly. If the thinking here resonates and you’re curious about working together, you can learn more about my services or get in touch here.
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