The thing holding you back isn’t the market. It’s not what your competitors are doing.
It’s your old beliefs and habits.
The way you’ve always done things. The things you swore you’d never do. The fears you’ve dressed up as principles.
As a founder, there will be times you need to reverse course on a stance you’ve held for years—and that can be scary as hell!
Here’s my take on how to find the right time to change your mind for the good of your business.
How Good Beliefs Become Bad Strategy
For more than a decade, any time someone on the team brought up the idea of sharing our product roadmap, my answer was simple: No.
Not maybe. Not later. Just flat-out no.
Why? Because I didn’t want to bullshit anyone.
I’ve seen too many SaaS companies overpromise, underdeliver, and burn trust in the process. Flashy launch videos, hyped-up features that either never ship or arrive so broken they’re unusable—it never sat right with me. I didn’t want Close to be like that.
I thought: “We’ll never overpromise and underdeliver. We’ll only promise things that are 1000% ready.”
I told the team there would be no forward-looking promises, no public roadmap, no commitments unless we were already deep into the build.
Sounds noble, right? That belief came from a good place—we wanted to be radically honest. It helped us build a reputation as a product you could count on. We were making a statement that we’re a company with unquestionable integrity.
And maybe my decision was about integrity at first. But the bigger reason?
Fear.
Fear of disappointing people. Fear of committing to something and missing the mark. Fear of making a promise and not being able to keep it. We prided ourselves on shipping rock-solid software. But in our pursuit of perfection, we began to avoid transparency. And we masked that fear as “principle.”
That’s the trap: you convince yourself that your old habits are virtuous, when really, they’re just comfortable.
But comfort doesn’t lead to growth. Courage does.
What Finally Changed
This year, our product team came to me with an idea: “Let’s do a product roadmap webinar.”
My first reaction? Flashbacks of every time I’d said no to that exact idea over the past 12 years.
Then I caught myself. The company has changed. The product is more mature. Our customers are more invested. And more than anything, I’ve changed as a founder and CEO.
Growth isn’t just about scaling your product or your revenue. It’s about evolving your mindset. Looking in the mirror and asking: What am I clinging to that no longer serves us?
Leading a company means knowing when your old answers don’t serve the current version of your company anymore.
My team had a ton of conviction about sharing what we’re building with our customers, so this time, I said: “Let’s go for it.”
Finding the Middle Ground on Your Way to Change
You don’t have to choose between two extremes to make meaningful change.
For me, there was a middle ground between becoming a hype machine and staying silent forever.
In any change you’re considering, there’s usually a golden middle.
You can be transparent without being reckless. You can be ambitious without overpromising. You can show your cards without showing all of them.
Our first-ever product roadmap webinar was a big moment for us. We didn’t know what to expect, but the response blew us away.
The turnout was huge. The energy was real. Customers were fired up to hear what we’re building. They asked smart questions. They gave great feedback. And they left more excited than ever to grow with us.
The topic even attracted prospects and re-engaged churned customers—an outcome that really surprised us. It turns out even non-customers are interested in learning more about where your product is going.
We realized: people don’t expect perfection. They just want honesty. They want to feel like they’re building alongside us, not waiting in the dark.
It made me wish I had changed my opinion sooner.
Action Items for Founders
As a leader, you need to have the courage to challenge your own default thinking and make decisions that a past version of you wouldn’t have been comfortable with.
Ask yourself:
- What rules or habits have you outgrown—but you’re too stubborn to admit it?
- Where are you hiding behind “playing it safe” when you should be leading with courage?
- What fear are you mistaking for wisdom?
Growth starts when you’re willing to do the uncomfortable thing. To break your own pattern. To admit that something that once served you well is now in your way.
It’s not easy. But that’s the job.
Like Musashi said: “It may seem difficult at first, but all things are difficult at first.”
Check out Close’s 2025 Product Roadmap webinar in the video below.
