Why Your Startup Strategy Needs a Post-Breakup Reality Check
By Dante — Emotionally available. Yes, we exist. No, I won't explain your ex to you. Okay fine, I will. ·
Stop Building for a Version of Yourself That Doesn’t Exist
I spent five years with someone who I thought was my endgame. When it ended, I spent six months trying to 'optimize' myself to fit the version of me they wanted—or at least, the version of me I thought would have kept them around. It was a massive waste of energy. It’s the same trap I see founders fall into every single day in the Chicago tech scene. You aren’t building a product for your actual customers; you’re building a product for a hallucinated version of a market that doesn’t exist, just to validate that your 'vision' is correct.
In UX, we call this the 'False Consensus Effect.' You assume everyone thinks like you, wants what you want, and has the same tolerance for friction that you do. Spoiler: They don’t. If you’re two years into building a startup and you’re still waiting for the market to ‘get it,’ you aren’t a visionary. You’re just stubborn. And honestly? Stubbornness isn't a strategy, it’s a security blanket.
The 'Emotional Debt' of Your Cap Table
We talk about technical debt all the time, but nobody talks about emotional debt. You know that co-founder you brought on because you were lonely at 2:00 a.m. and you needed someone to talk to? Or the investor you took money from because their name looked good on a press release, even though your gut screamed ‘run’? That’s emotional debt, and it accrues interest faster than a payday loan.
In therapy, I learned that if you don't address the underlying issue, you’ll just keep attracting the same toxic patterns. Startups are exactly the same. If you start your company by compromising on values to get a quick win, you’ve baked that compromise into the DNA of the firm. You can’t pivot out of a broken foundation. Before you sign another term sheet or hire another ‘rockstar,’ ask yourself: Am I doing this because it’s the move, or because I’m scared of what happens if I don’t?
UX Isn't Just Visuals, It's Empathy
I’m a UX designer. My job isn't to make things pretty; it’s to make things usable. If your startup advice has been ‘move fast and break things,’ I’m here to tell you that’s outdated. The modern equivalent should be ‘move deliberately and fix things.’
Stop trying to reinvent the wheel. If you’re building a SaaS platform, don’t try to innovate on how a user logs in. Nobody wants a ‘disruptive’ login page. Use standard patterns, provide value, and get out of the way. Your users are already overwhelmed, tired, and probably dealing with their own version of a breakup or a existential crisis. If you add friction to their lives, they will leave you, and they won’t look back. Treat your user’s time with the same respect you’d want someone to treat yours. If you aren't solving a pain point, you’re just creating clutter.
The Art of the 'Clean Break'
Sometimes, the most successful thing you can do is kill your darling. I once spent four months designing an interface for a feature that nobody used. I was so attached to the aesthetics that I ignored the analytics. It took me a long time to learn that being a founder means being able to let go of your ego.
If your product isn't working, have a clean break with it. Don’t drag it out. Don’t try to ‘fix’ it with a new marketing campaign or a rebrand. If the core value proposition is dead, let it go. Mourn it, learn the lesson, and move on to the next project. There is no shame in a pivot. There is only shame in staying in a relationship—or a business model—that stopped serving you years ago.
Practical Steps for Sanity
If you want to survive the next year without losing your mind, try this:
1. The 3-Month Audit: Every quarter, look at your primary feature. If it hasn't gained traction, kill it. Not ‘pause’ it. Kill it. 2. The 'No' List: What are you not going to do? Most founders are great at saying yes to everything. The real pros are the ones who say no to 90% of the opportunities that come their way. 3. Therapy (or a sanity check): If you don’t have a mentor or a therapist who isn't on your payroll, get one. You need someone who will tell you, ‘Dante, you’re acting like an idiot,’ when you start spiraling. Everyone needs a reality check.
Building a startup is hard. It’s messy, it’s frustrating, and it’ll show you parts of yourself you didn’t know existed. But it doesn’t have to be self-destructive. Treat your company like a healthy relationship: set boundaries, communicate clearly, and know when to walk away before you’re both miserable.
Anyway, that’s my two cents for this week. I’m going to go grab a coffee and try to remember what it’s like to not think about conversion rates for ten minutes. If you’re spiraling over a pivot or just need to vent about why your co-founder is acting like your ex, hit me up. I’m around.