I’m so excited to share with you the latest Creator Diaries interview! Today’s edition is with Jenni Gritters, a coach, consultant, and fellow ex-journalist, who’s just published The Sustainable Solopreneur. I’ve followed Jenni’s work for years and have always admired her refreshing takes on business and finding alignment, and it has been a major encouragement for me in my own journey.

In her book, Jenni says that building a business you love can feel at times like a “revolutionary act.” And yet, that’s what so many of us are trying to do. It’s countercultural in many ways but still entirely possible nonetheless.

We talked about what it means to create a business that evolves with your life, how to know when it’s time to pivot, why “doing it all yourself” isn’t always the badge of honor it seems, and so much more. (Full Q&A below!)

Q: I just finished reading your book Sustainable Solopreneur, but I’ve followed your work for years and it really speaks to what I’m learning in my own business. I wanted to bring you on to talk about your work, how you’re thinking about solopreneurship, and to share some advice for others navigating this world of business. Could you start by introducing yourself and where you focus your work these days?

A: I’m Jenni Gritters. I live in Central Oregon and have a million and one titles — I use a different description every time — but I’m a business coach and strategist for solopreneurs. I primarily work with creatives, multi-passionate people, and folks who don’t fit into the standard box or have capacity limitations. My focus is helping them build sustainable businesses that don’t burn them out, businesses that work for years and evolve as they grow.

I was a journalist for over a decade, so I’m also a writer. I’m a mom of two little kids and a big outdoors person. Most people online know me for my coaching and my writing.

Q: The tagline of your book is about building a business you love that doesn’t burn you out. How does that go against the traditional model of entrepreneurship?

A: I recently had a client who was told she needed to fit into a niche and be able to explain what she does in one phrase. Most of the people I work with just don’t operate that way. I see our businesses as puzzles — different elements of our work and selfhood come together and shift over time.

Flexibility and evolution are healthy and normal, but the business world often tells you to build one thing that stays the same, like one revenue stream, one message. That rarely works for most people, including me. 

It’s a more human, messy, complicated process to run a business this way, but that’s essential. I’ve seen many people struggle mentally because they’re stuck in a model that doesn’t fit anymore. My work pushes back on the hustle-and-grind mentality and focuses on well-being and change without apology.

Q: Do you think people struggle with the idea that work can actually feel enjoyable — that it doesn’t have to be constant struggle?

A: Definitely. Many of us grew up watching our parents suffer at work, so we internalized that as normal. My dad hated his job; my mom was miserable as a stay-at-home parent. That programming runs deep — this belief that making more money means working harder and being more exhausted.

I’ve had experiences that disproved that, but it takes time for people to believe it’s possible. We’re in a paradigm shift right now. People are starting to question whether work really has to be that bad.

Q: It seems like more people are open to experimenting and challenging old assumptions, but it’s hard to know how to actually do it.

A: It’s both mindset and strategy. You have to be brave enough to experiment first, then you can build strategy on new assumptions. Every strategy comes from a set of core beliefs. If we change the beliefs, the strategy changes. That’s why I describe myself as both a coach and a strategist. They go hand in hand, but mindset work comes first.

Q: You do a lot of different things — coaching, writing, running programs. How do you know when to pivot or take the next step in your business?

A: It probably looks like I know exactly when to jump, but it doesn’t feel that way. There’s always a messy in-between — a titration process — where the old and new coexist for a while.

When I shifted from journalism to running a content agency and then to coaching, those things overlapped for years. This is the first year all my revenue comes from coaching, and I’ve been doing it for five years. So, permission for it to be gradual is important.

Intuition also plays a big role for me. I have a strong gut about when a gamble is worth taking. But it’s always a risk, especially with your audience, because changing directions can confuse people. You have to let it be messy.

Q: How do you coach people through that transition?

A: I use what I call the bridge metaphor. You have your current business on one side and the one you want on the other. Most people want to blow up the first and jump straight to the second, but you have to walk across the bridge.

That’s what I do as a coach - walk with clients across. Sometimes that means slowly integrating the new ideas into existing offers or messaging. It’s not instant, but after a few months, they look up and realize their brand has shifted and they’re ready for the new phase.

Q: Let’s talk about offer design. You’ve written that there are endless ways to build an offer. How do you approach it creatively while staying aligned with your capacity and goals?

A: Offer design is one of the most creative spaces we have. There are the usual models, but I think there are hundreds more if we allow ourselves to play.

I start by checking in on my capacity. I work about 25 hours a week because I have two small kids, so I avoid high-touch offers beyond my one-to-one clients. Then I think about goals — where the offer fits in the overall ecosystem. I see my offers as rings of a tree, moving people toward the center.

Finally, I add a layer of surprise and delight. In my eight-week Create program, we use visualization and even arts and crafts to imagine what an offer would look and feel like. It helps people come up with unconventional ideas that resonate more deeply. And yes, we still test and make sure it solves a real problem, but it should be fun.

Q: You came into entrepreneurship almost accidentally. How did that shape your approach to business?

A: For sure. I don’t think I have any preconceived notions about “supposed to’s.” I was in a mastermind last year with a bunch of coaches, and I’d honestly never been part of the online coaching world before. I came into coaching from journalism because people were asking for it, not because I was following the coaching conversation.

So I was kind of startled by how many people were trying to duplicate the same thing. I actually think that’s been a blessing. Whenever someone tells me they don’t even know how to run a business, I say, “Amazing. Sounds good.” Because that means the sky’s the limit. We can do whatever you want since you don’t have those preconceived notions.

I think that’s why my business has always worked well — I’m just building what my audience wants and what’s interesting for me.

Q: That’s an interesting point that comes up a lot when I talk to creators — this idea of a two-way relationship with your audience. How do you think about building that connection and listening to your people?

A: I’m always talking to my people. I have what I call an evolutionary model of offers. I start with a lower-ticket community program called Sustain, and then people can move into intensives, and eventually into The Council or my one-on-one work.

Most people start by following my newsletter for a year or more before they join Sustain. It’s a long pipeline — sometimes four or five years (!) — and I actually prefer that. It feels really safe to know there are hundreds of people making their way through that process.

I listen constantly. Sustain is where I hear what people are struggling with. For example, I recently did an intensive about visibility because ten people asked me for coaching on that topic in the same week. I thought, “Okay, something’s going on here.” I couldn’t take all of them one-on-one, so I created a two-week intensive.

If your offers or marketing aren’t landing, that’s usually the problem: you’re not listening closely enough. People will tell you what they need. It might sound almost too simple, but they say it out loud. The key is making sure it also works for you to offer it.

Q: You’ve said people can stay in your world for years before working with you, which is pretty different from the “get the lead, close the lead” mindset.

A: I know. I actually hate the word leads. These are humans.

Because I’m an introvert, I don’t want to chase or coerce anyone into a sale. When someone books a free 20-minute call with me, they usually already know they want to work together because they’ve been in my world for a couple of years.

It’s not a quick-growth approach. I’m not here to teach people how to go viral or chase shiny-object strategies. I’m here to help them build something long-term. That’s less sexy and takes longer.

But that’s the point—it’s repetitive action. I’ve published my newsletter every week for three years. When people ask, “How does it convert?” I tell them, That’s how. Three years of consistency.

Q: Let’s talk about sustainability. I think everyone has those seasons where their business feels amazing, and other times when it feels impossible. What ingredients make a business truly sustainable?

A: The ebb and flow is completely normal. I go through those seasons all the time. In the spring, I had one of those moments where I just couldn’t make myself move. I didn’t want to do anything. But that period actually led to a huge leap forward.

In the book, I outline five core principles of sustainable solopreneurship:

These principles act as anchors. When things feel off, I go back to them and ask, “Which one needs attention right now?”

Q: You wrote that a business of one is a mirror for your own brain, which is both true and terrifying. How should solopreneurs approach the mindset side of the work?

A: When I first started coaching, I focused only on strategy — marketing, revenue goals, operations. But clients wouldn’t implement, even when the plan was solid. That’s when I realized mindset and energetics matter just as much.

We all have programming from how we grew up. When you work for someone else, there are external rules. When you work for yourself, your rules become the operating system. So if you believe there’s never enough money, you’ll build a business that reinforces scarcity.

When people start to chip away at those beliefs, they open up more space to create things that work better. It’s ongoing — there’s no finish line — but every iteration of my business has forced me to face a new pattern. For me, one of the biggest was carrying everything on my shoulders alone. I had to unlearn that or I was going to burn out.

Q: That ties perfectly into another topic you write about: doing it all yourself. You call it “toxic self-reliance.” Can you explain what you mean by that?

A: I think a lot of us drawn to solopreneurship have old wounds around needing to do everything alone. My husband once tried to build a business and said, “This is insane. Why do you do this?” He didn’t have that conditioning.

Many of us who do become entrepreneurs are used to carrying a lot. We’re resilient. We can handle discomfort. But that same strength can become a trap. I call it toxic self-reliance, carrying a boulder up a hill by yourself when you don’t have to.

Learning to let others help is a nervous-system regulation process. It’s not natural; it takes practice, almost like exposure therapy. Start small — you can hire a VA, delegate a few things. But eventually, you’ll hit your capacity limit. For most people, that happens around 12–13K months, depending on the business. You can’t scale beyond that without help.

Q: You’ve also talked about how freedom looks different for everyone, and how your own definition keeps evolving. How are you thinking about that now?

A: Yeah, I’m actually in the middle of one of those inflection points. I have 22 one-on-one clients, I’m running multiple intensives, and I have a group program with over 100 people.

I realized I probably need to hire a second person. I have one contractor now, and when I looked at the numbers, I saw I have about a 90% profit margin — which is kind of wild for a business my size. It would be totally fine to bring that down to 70% to buy back some time.

It’s funny, because part of me wonders, “Am I allowed to change my mind?” Especially when I’ve told people how much I love being lean and simple. But the truth is, you’re the one who has to run your business. You’re allowed to evolve. What you wanted two years ago might not be what you want now — and that’s normal.

Q: You’ve described entrepreneurship as an act of faith or hope. What do you mean by that?

A: When people ask me what it’s like to be a business coach, I always say it’s never really been about business. It’s about growth — stepping into your own power, visibility, prosperity, and confidence.

For the people I work with, entrepreneurship is often a calling. Everything we create also creates us. That’s how I see it — with my book, my programs, everything. It’s an inside-out process.

When people hit frustration or a plateau, it’s usually because they’re about to reach a new level of awareness or empowerment. That’s why I describe entrepreneurship as an act of faith or hope. Every time you wonder, “Does this make sense? Should I keep going?” you’re making a hopeful choice to believe something better is possible.

You don’t just choose this path once—you choose it over and over again. Every three to six months, you recommit. For many of us, business is a way of believing in a new kind of power — one where creativity and autonomy shape what comes next. It’s a hopeful, even revolutionary, act.

Q: Where can people find you and your book?

A: The Sustainable Solopreneur is now available on Amazon and through my website, jennigritters.com/thebook. You can find me on LinkedIn or Instagram at @jennigritters.

If you want to go deeper, I also have a free masterclass on implementing the five principles from the book — it includes a lot of practical, tactical strategy. You can find that on my website too.