Solopreneur at Three Years: What’s Working, What’s Not, and What Comes Next
Three years ago, I left a full-time Chief Revenue Officer role and started advising part-time while looking for another full-time job. That search never quite ended. Instead, I leaned into independent consulting, and by 2022, it became my full-time business.
I didn’t have a formal plan. I wasn’t building a brand. I just started writing, sharing my thoughts on LinkedIn and Substack, and taking on projects that came my way.
Now, consulting is my only job—essentially a 9-to-5, but without a boss or a guaranteed paycheck. I handle everything myself: content creation, sales, delivery, and accounts receivable.
This article is not a how-to guide. I don’t recommend that anyone go out on their own. But if you’re considering it, here’s what I’ve experienced.
The Mindset Shift: It’s About Options, Not Titles
A quote that sums up where I am right now:
“The most valuable career advice I can offer is this: don’t fixate on becoming an executive, or a founder, or a solopreneur, or [insert your dream role here]. These shouldn’t be seen as ultimate goals but rather as options you should work to have available to you.”
— Elena Verna, Growth Leader at Dropbox and Product-Led Growth Consultant
I like this framing because I don’t know how long I’ll keep consulting. I’ve kicked around a few ideas of what the future could look like. For now, I’m trying not to stress about it.
My focus is simple: do great work and see where that takes me.
How Is This Different from Being a Full-Time Sales Leader?
There are two ways to look at this:
Advisory Work – Part-time, high-value support for multiple companies.
Interim Roles – Temporary full-time leadership roles, stepping in as CRO or VP Sales.
1️⃣ Advisory Work (My Preferred Model)
Most of my work is as an advisor. I partner with startups and established companies launching new products, typically through weekly calls and strategic projects.
These relationships last anywhere from a few months to more than a year. The fact that my average engagement length is increasing is a good sign—it means partners see ongoing value beyond solving an immediate challenge.
What Do I Actually Do?
✅ Sales & GTM Strategy – Evaluating messaging, pipeline management, and analytics.
✅ Coaching – Helping founders and teams avoid common mistakes and build strong sales discipline.
✅ Pattern Recognition – Applying insights from similar businesses and industries to save time and effort.
✅ Challenging Leadership – Asking tough questions that internal teams may avoid.
✅ Being Available – Clients can reach out for quick, high-value discussions. I keep my client list small so I can respond quickly.
✅ Honesty – If I don’t know the answer, I say so. If I’m not the best person for something, I refer them to someone who is. Trust matters more than trying to be the smartest person in the room.
2️⃣ Interim Roles (More Money, More Stress)
Interim roles are high-pressure, high-stakes. The job is to get in, fix things, and set up the next leader for success.
They pay well but come with more stress than advisory work. I only take them when the challenge and timing are right.
What’s Unique About Interim Work?
✅ Preserving Future Options – I try not to make decisions that limit my successor. Avoiding major restructures unless necessary.
✅ Managing People, But Temporarily – Building trust is harder when everyone knows you’re only there for a few months. I frame my role clearly: I’m here to help you fix what’s broken.
✅ Hitting the Ground Running – There’s no learning curve. You need to be ready to do the job on Day 1.
✅ Tactical Work Over Strategy – Companies don’t need more theories. They need execution. Often, they bring in an interim leader because something urgent is broken.
✅ Contracts Should Be Clear & Flexible – I don’t take interim roles unless they:
Pay market rates. (Base + full equivalent of what would normally be variable.)
Have a clean exit plan. Ideally, I help hire and onboard my replacement.
Why I Don’t Like the “Fractional” Model
A lot of people are experimenting with fractional executive roles—basically, splitting one job across multiple companies.
I’ve found this to be a full-time job for part-time pay.
I’d rather:
🔹 Go deep as an interim CRO.
🔹 Stay focused and targeted as an advisor.
For me, the middle ground doesn’t work. But I know others have made it work well.
How I’ve Kept a Steady Flow of Work
1️⃣ I Don’t Do Outbound Sales
I don’t do cold emails or direct outreach. I’ve tested it, and the results weren’t great.
The few times I’ve pitched companies directly, I got polite declines—not because they didn’t like me, but because the timing wasn’t right.
Instead, I’ve relied on inbound leads and referrals.
2️⃣ Clients Stick Around (or Come Back)
I focus on long-term relationships instead of constantly hunting for new clients.
Here’s how:
✅ Make sure clients are happy. Overdeliver, especially in the first 30 days.
✅ Charge appropriately. I don’t try to hit a “market rate” that doesn’t fit their needs.
✅ Keep it simple. I avoid overcomplicated contracts, pricing models, and negotiations.
3️⃣ Social Media (Mostly LinkedIn)
I post on LinkedIn regularly—that’s been my best source of business development.
A lot of people hesitate to post because they don’t want to self-promote. My approach is simple:
📌 I share what I know, based on what I’m working on.
📌 I don’t try to “sell” my services in my posts. That happens naturally if people find value in what I share.
Most of my client conversations start with something they saw me post.
4️⃣ Consistency > Big Marketing Efforts
Right now, my goal is:
📌 2-3 LinkedIn posts per week
📌 1 Substack article per month
I don’t always hit it, but I’ve learned that steady, useful content compounds over time.
Do I Need to Be an Industry Expert?
No.
What has mattered more than industry knowledge is:
📌 Understanding business models (SaaS, consulting, enterprise sales).
📌 The ability to learn quickly and teach effectively.
That’s what allowed me to sell into healthcare, big tech, finance, and other large industries—and now, as a consultant, to work with startups and scale-ups across different sectors.
That said, I only take projects where my experience qualifies me for a senior full-time role in that company.
How Do You Know If You’re “Good Enough” to Do This?
Impostor syndrome is real.
When I started, I felt like an impostor every day. What I learned:
📌 Everyone else is winging it too.
📌 You’re probably an expert at something that feels easy to you.
📌 You don’t have to be great at everything—just avoid the projects you aren’t good at.
One thing that helped? Starting with lower fees. It took the pressure off and helped me figure out what I was best at.
Now, I’ve raised my rates every year—and I’ve never had a client push back.
Final Thought: If You Want to Start Something, Start
You’ll figure it out along the way.
I’ve had the benefit of great colleagues and mentors—many of whom have gone out on their own.
If you’re thinking about doing the same, talk to people who are a little ahead of you. It’s one of the best ways to learn.
And if you’re already doing this—how’s it going for you?