A few months ago, I joined an entrepreneur mastermind in which we had to share our tangible goals. Of course, I had my goals ready to go, but as the conversation unfolded, I found myself thinking about the bigger picture.
Having just said goodbye to my soul dog, Tessie, the last thing on my mind was numbers.
My real goal was to learn how to live with this loss, to maintain my business while embracing my grief. But that doesn’t exactly translate to a number or a percentage, now does it?
And that’s the issue.
We live in a world where success is measured by numbers. Money in the bank, social media likes, ROI, pounds on a scale, days in a row. Yet we also recognize that so many of life’s most important accomplishments—happiness, health, and love—cannot be measured on a scale or tracked in a spreadsheet.
No one understands this tension better than a high-achieving entrepreneur, especially one juggling multiple businesses, limited bandwidth, or a major life change.
You become an entrepreneur for the joy of building something meaningful. Yet the numbers still matter because, unfortunately, life costs money. Because of that, it can be difficult to fully appreciate non-numerical wins, like time freedom or meaningful impact.
What’s even harder is knowing when to stop, pause, or celebrate. That requires radical self-awareness. Even those of us with a strong sense of self can struggle to step back when momentum is still carrying us forward.
The trouble is that when you don’t pause to reflect and reassess, an invisible rift can begin to form in your business. You don’t notice it at first because outwardly, things are still working. Maybe you feel a bit burned out or unmotivated, but you keep going because it feels easier. And frankly, because you can, especially when you work for yourself.
This slow-burning misalignment likely resonates even if you do not work for yourself. We live in a culture that prizes perseverance at all costs. We are trained to keep going whether things are good, bad, or neutral. In entrepreneurship, especially, pushing forward is often framed as a virtue.
On top of that, people do not like talking about what is not working when there are no clear numerical signals. Even more than that, people do not like talking about potential issues when things appear to be working.
But a true leader knows when it is okay to take a beat. They understand that recalibrating is not a sign of weakness. It is a sign of strength. There is wisdom in recognizing when a small misalignment could become something much larger.
Taking time to pause, even when it feels unnecessary or uncomfortable, is a hallmark of a mentally fit founder.
In my case, I took two important pauses in my business recently. One was short and highly tactical, while the other was more fluid.
As Tessie’s health declined, I took time to develop a feasible plan for a longer bereavement period. I did not know what that would look like, so I avoided setting dates or rigid rules. Instead, I created a loose plan centered on ongoing communication with my team.
There was absolutely no part of me that wanted to plan for when my dog passed away. But I did it because I knew future me would be grateful. Giving myself permission to pause and reflect on what I would need allowed me to fully grieve when the time came.
Something else happened when I gave myself space to process my grief–unexpected progress in my business and my mental health work.
My goal was simple–I did not want to overwhelm myself. I wanted to take those first few days to cry in bed and just be. I did those things, but that space also allowed my thoughts to wander and eventually deepen.
When I first started my business, my “why” was spending more time with Tessie and Jon. When one half of that why was suddenly gone, I was forced to confront larger existential questions about what I want from my business now.
At the same time, I began thinking about my mental health work more deeply and intentionally. I realized just how much more I had to say. That clarity led me to make a few small but purposeful changes, including starting a Substack.
While my true bereavement period lasted about a week, I spent the following months lying low. I let my friends and family love on me. I traveled to sunny Florida to get some much-needed vitamin D. I spent time with my nephews. Most importantly, I did not force anything–I let things unfold.
Living in the moment-ish was exactly what I needed. Today, I feel energized and genuinely excited about what is next.
I know it can be hard to pause and ask yourself difficult questions. But I promise you will never regret taking time to reflect.
Here are a few questions I invite you to sit with in your own work:
Does this work feel good right now?
Does it support a strong mental state?
Are my processes serving me, or are they performative?
What would I love to do with my work?
Is my time aligned with what matters to me?
What am I doing out of habit, not alignment?
Where am I mistaking consistency for obligation?
That last question is what ultimately led me to rethink my mental health work. Was I posting monthly newsletters and occasional Instagram updates out of passion, or because I thought I should?
I realized the issue was not obligation—it was limitation.
I wanted to share more, like longer reflections, deeper musings, and more honest conversations. But I did not have the right container. Substack felt like the space that finally matched the work I wanted to do.
As founders, we often assume the hardest work is building the business or refining the service. We also assume pauses mean stepping away from the work entirely.
But sometimes the hardest and most important work is the pause itself. And pausing does not always mean stopping. Sometimes it simply means stepping back from the day-to-day to reconnect with the bigger picture.