Recently, I've heard the term serial entrepreneur come up a few times.
And every time I hear it, I find myself thinking, Gosh, I hope that's me someday.
There's something about the idea of building businesses, creating opportunities, and turning an idea into something real that genuinely excites me.
Not necessarily because I want to own a dozen businesses or have my hands in everything. But because I love the process of creating something. I love imagining what could be, figuring out how to make it happen, and watching an idea slowly turn into something tangible.
And the more time I spend as a business owner, the more I realize that entrepreneurship is both one of the most fulfilling and one of the most challenging things I've ever experienced.
Sometimes those two feelings exist in the very same moment.
The Kind of Brain That Doesn't Turn Off
I don't know if this is true for every entrepreneur, but I know it's true for me.
My brain is constantly going.
There's always another idea, another opportunity, another way to improve something, or another project I'd love to bring to life.
Sometimes I'm thinking about how to make HomeGrown better. Sometimes it's a community initiative. Sometimes it's an entirely new idea that I haven't quite figured out what to do with yet.
And while I recognize that can be exhausting, it's also something I'm incredibly grateful for.
I genuinely enjoy thinking about possibilities.
I love the planning stages, the conversations, the collaboration, and even the problem-solving that comes with bringing something new into the world.
There's a particular kind of excitement that comes from looking at something that doesn't exist yet and thinking, What if it could?
But having a mind that's always looking for what's next comes with its own challenges.
Because sometimes it's difficult to know when to turn it off.
The Guilt of Taking a Day Off
Yesterday, I was sick.
Not the kind of sick where you feel a little under the weather but can push through your day.
The kind where getting out of bed wasn't really an option.
So I stayed home.
Which sounds like a perfectly reasonable thing to do, right?
And yet, I felt guilty.
Guilty about the things I wasn't getting done. The conversations I wasn't having. The work that would still be waiting for me tomorrow.
And at some point, I caught myself thinking about how ridiculous that was.
I was sick. I needed rest. There wasn't anything particularly complicated about that.
But when you're responsible for your own business, it can feel like every hour you're not working is an hour you're falling behind.
Even when nobody else is putting that pressure on you.
Sometimes, especially when nobody else is putting that pressure on you.
I think that's one of the harder parts of entrepreneurship to explain.
You can have the flexibility to take a day off and still struggle to give yourself permission to actually take it.
And I'm learning that those are two very different things.
Freedom Doesn't Always Feel Like Freedom
One of the things I appreciate most about being a business owner is the ability to make decisions about my own time.
If something unexpected happens, I can adjust.
If an opportunity comes along, I can explore it.
If an idea doesn't work the way I thought it would, I can pivot and try something different.
There's a freedom in that flexibility that I don't take for granted.
But there's also a responsibility that comes with it.
Nobody is necessarily telling you when to stop working, when you've done enough, or when it's time to take a break.
You're the person setting the expectations.
And if you're anything like me, those expectations can be pretty high.
I've realized that just because I have the ability to do more doesn't always mean I need to.
Just because I can answer another email, plan another event, or take on another project doesn't mean it all has to happen today.
And just because something didn't go according to plan doesn't mean the entire plan is falling apart.
I know all of those things logically.
Putting them into practice is another story.
But Goodness, I Love Building Something
Here's the thing.
Even with the pressure, the uncertainty, the exhaustion, and the occasional guilt, I genuinely love being an entrepreneur.
I love having an idea and watching it grow.
I love creating a brand that means something.
I love collaborating with people who see the potential in something and want to help bring it to life.
I love walking into HomeGrown and knowing that something I once imagined is now a real place where people work, grow, and connect.
And I love that there are still so many things I haven't done yet.
I think that's the part of entrepreneurship that brings me the most joy.
The possibility.
The idea that the business you have today doesn't have to look exactly like the business you'll have five years from now.
That you can learn something, change direction, build on what works, and keep discovering new opportunities.
Not every idea will be successful.
Not every project will turn out the way you envisioned.
And not every day will feel particularly inspiring.
But there's something incredibly rewarding about having the opportunity to try.
Learning to Give Myself a Little Grace
I think one of the things I'm going to have to continue working on is finding the balance between being driven and being kind to myself.
Because I don't want to lose the ambition.
I don't want to stop dreaming, creating, or challenging myself.
I love that part of who I am.
But I also don't want to spend so much time worrying about what I haven't done that I forget to enjoy what I'm doing.
And I certainly don't want to feel guilty for being human.
For needing rest.
For having a day when things don't go according to plan.
For occasionally having to set something aside and come back to it tomorrow.
If I want to continue building businesses and exploring new opportunities for years to come, I have to recognize that I'm part of what makes those things possible.
And taking care of myself isn't separate from taking care of my business.
It's part of it.
Maybe Someday I'll Be a Serial Entrepreneur
I don't know exactly what the next chapter of my entrepreneurial journey will look like.
And truthfully, that's part of what makes it exciting.
I have ideas. I have dreams. I have things I'd love to create and opportunities I'd love to explore.
Maybe someday I'll look back and realize I've become the serial entrepreneur I keep hearing about.
But I hope that when I do, I've also learned a few things along the way.
How to recognize when something deserves my energy and when something can wait.
How to celebrate an idea becoming reality without immediately worrying about the next one.
How to embrace the flexibility of entrepreneurship instead of filling every available moment with another responsibility.
And how to take a sick day without feeling like I've somehow let everyone down.
Because I don't think the goal should be to build as much as possible at the expense of everything else.
I think the goal is to build things you believe in while creating a life you genuinely enjoy living.
And if I'm fortunate enough to keep doing that, whether it's with one business or several, I think that's a pretty wonderful dream to chase.
Ashley Dudley | Broker Owner HomeGrown Real Estate
ashley.dudley@homegrownreva.com
540.271.1655