Letter to the Tired Entrepreneur
From my founders heart to yours.
Letter to the Tired Entrepreneur,
It can all feel like a lot, right?
No matter how much we love our work, our clients, our products… the nature of business ebbs and flow, just like everything else in life.
QUESTION: How are you doing right now?
That’s a serious question, and if you reply back to that, I’ll personally respond.
Founder, I see you.
I see the hidden burdens you carry. The late nights and early mornings; taking care of yourself and everyone else in your household. The wifi going out right before you save a project. The accidental double bookings. The collaborations that go sideways. The events that get messy. The hires that are immediate regrets. The meetings that feel like a waste of time. The clients who are disappointed. The investment that didn’t turn out as you hoped. The disappointment of sometimes feeling like you’re back at ground zero.
No matter how many years we are in business, there are times it feels like we are hitting the reset button.
And it can be so tiring.
We have all been there.
The four seasons of the year show up in our businesses, too. We need a winter, spring, summer, and fall. But we hate the winters.
Unpopular observation to say out loud: A lot of other founders are in their own version of winter right now.
When we started being an entrepreneur, we signed up for ongoing learning, consistent evolution, and a regular reckoning with our vision. The work we do is sacred, not matter what it is. And it doesn’t always feel good.
So if you’re in a winter, it’s OK to be tired and it’s OK to not know what’s next. Seasons of not knowing or a natural part of our business evolution and I want to normalize that.
Here are some of the the best ways to support yourself in a reset:
Don’t do it alone. Get clear on the kind of support you want and need. Is it mentorship, coaching, advising, therapy, or something else that you need right now? Not all support is the same. The specifics are ideal: “I want to solve/support ___ and the right professional is ___.”
Ask for help. Just this week alone, I reached out to a colleague who’s also a coach and does a certain kind of model in her work that I’m exploring right now. I asked for advice. I asked someone else to pick up my daughter from school. I asked a family member to handle errands. I asked a client to help with a DMV issue. Ask for help in and beyond your business.
Collect people of inspiration. Make sure that you are in communities, relationships, and rooms that fill you with a creative surge and stretch your thinking. What rooms have you outgrown? Leave them. Who out there reminds you of what’s possible? Reach out to them.
Embrace the unknowns AND the possibilities ahead. The unknown is always scary, but the possibilities are truly endless. The more you can relax into not having it all figured out, the more resilience you’ll create. But these are the seasons where seeds start to sprout and new ideas begin to reveal themselves. After winter, there is spring.
No matter what, we can always use support, no matter the season. Winter needs patience. Spring needs watering. Summer needs blooming. Fall needs shedding and reflection.
Whatever season you’re in, it’s the right one for now.
If you crave clarity on where you are and what you need, you can set up an intro call with me to explore your possibilities head.





Thank you! That was encouraging to me.