RR#125 - Pivot or persevere? Here's how to decide.
Real talk: As a founder, there are times when you’ve got to ask yourself: “Is it time for a pivot?”
Maybe your current offer isn’t getting the traction you expected. Maybe a shiny, new opportunity has landed in your lap. Or maybe you’re simply feeling the itch to try something different.
Whatever the reason, pivots are often glorified in the startup world, seen as the savvy, agile move that can save or supercharge your business.
But here’s the catch: a pivot comes with a substantial cost.
Most things in business operate on an exponential curve—meaning all the heavy lifting happens upfront.
That’s where you’re figuring out what works, how it works, and how to make it work better. The big results usually come later, after you’ve done the reps and put in the time.
A lot of founders confuse that initial grind with failure. They think, “This must not be working,” and they see a new opportunity that promises faster results.
So, they pivot. They start over. And they find themselves right back in that heavy-lifting phase.
Even worse? Some were likely on the verge of a breakthrough in their current venture. If they had just stayed the course, those exponential results would have kicked in.
Perpetually pivoting is a hard way to run a business.
That said, there are times when a pivot is the right call.
Some of the most successful companies started with one idea before pivoting into something better, driven by data and the opportunity to solve a bigger problem.
So, how do you know when to pivot and when to persevere?
I recently faced this very decision with a new opportunity that came my way. After going through the process myself, I’ve narrowed down five key questions that helped me make the call—questions I think will help you too.
1. Is This Aligned with Your North Star? (What I Call “Vision Founder Fit”)
It’s easy to get caught up in the money-making potential or market opportunity of a new venture.
And sure, those things matter. But they don’t matter as much as how well the opportunity aligns with you as a founder.
Do you have a clearly defined North Star? One that helps you filter opportunities and set boundaries so you can quickly assess how aligned you are with where the business is heading?
I call this Vision Founder Fit.
Beyond the financial upside, ask yourself: Is this a business that energizes you? Or will it ultimately drain you and lead to burnout?
For me, I prioritize location independence, flexibility, and autonomy. Your criteria may be different, but this is the first filter I use to make sure the opportunity aligns with who I am and what I want from my business.
2. How Far of a Departure Is This from What You’re Already Doing?
Here’s the thing: full-on pivots are expensive. You’re essentially starting from scratch in many areas—like building brand recognition, nurturing an audience, or developing systems that support growth.
The more disconnected the new opportunity is from what you’re already doing, the higher the cost.
That’s why I’m more cautious about true pivots and more open to evolutions—moves that build on the assets and systems I’ve already created.
For example, starting a sales consulting business for IT companies if you’ve been doing sales coaching with them for years? That’s more of an evolution. Starting a taco shop? That’s a full pivot.
The former is going to leverage what you’ve built, while the latter is a completely new game with way more risk.
3. What’s Your Real Motivation?
I’ve worked with hundreds of founders in the early stages of their business, when pivots are most common.
And I can tell you that a lot of pivots are emotionally driven.
They usually stem from one of two things:
Feeling resistance in the current business and romanticizing the new opportunity as easier than it’s going to be.
Being addicted to change and chaos.
When you let these mindsets hijack your brain, you’re not making decisions objectively. Understanding your deeper motivations—what’s truly driving this desire to pivot—is critical to making a sound choice.
4. Are You Overlooking Opportunities Where You Are?
The grass often looks greener on the other side, but as the saying goes, many times that’s because the grass across the street was just cared for better, or for a longer period of time.
You aren’t going to get those same results if you keep re-sodding your yard every 6 weeks.
Many times, you’re just one or two small changes away from the results you want. Before you jump ship, ask yourself: Are there similar opportunities within your current business that you’re not seeing?
Look around. Are other people succeeding in your field? If so, why aren’t you? Is the pivot really going to solve your problems, or are you missing opportunities right in front of you?
5. Are You Building with “Paddles” or “Sails”?
A friend of mine once said, “You can build any business if you’re willing to paddle hard and long enough. But the best businesses are built with sails.”
What does that mean?
If the new opportunity comes with a unique advantage—contacts, access, or information that makes success more likely—it might be worth the risk. That’s what I call throwing up a sail.
But if this new opportunity requires just as much hard paddling as what you’re already doing, you may be better off sticking with your current business and putting in the reps.
Bonus: Will ‘Future You’ Be Having the Same Conversation?
Fast forward 24 months. Be brutally honest: Will you be having the same conversation with yourself about the next “big idea”?
If you have a history of pivoting or struggling to stick with things, this is crucial to recognize.
There’s a high chance that the shiny new opportunity will feel just as hard in two years.
In that case, the best thing you can do is stay the course and build the discipline of stick-to-itiveness. It’ll serve you in the long run.
These questions helped me navigate my own decision-making process around a new business opportunity. I hope they’re helpful for you too as you consider the next pivot—or evolution—in your business.
As for me? I ultimately decided to move forward with this new opportunity (more details coming soon), but it wasn’t a drastic pivot. It was an evolution—one that I feel confident about.
I’ll be documenting the journey and sharing updates with my community. If you’re interested in following along, keep an eye out for more details below.
