How to keep your pipeline full and have financial security as a solopreneur

“Financial security isn’t having money in the bank. It’s knowing you have the ability to make money when you need to.”

I heard Pia Silva say that on her podcast three years ago, and it lodged itself forever in my brain, body and soul.

Earlier this year, I got to test that idea.

After a great 2025, when I was booked out with a waitlist for much of the year, things suddenly got very quiet. At the end of 2025 and into early 2026, hardly anyone was booking sales calls.

Normally the end of the year is busy for me. People start preparing for fresh starts in the new year. But not last year!

I was a little freaked out and wondering if AI had come for me already (spoiler: we’re not there yet).

But over the next few months, I made some changes and things started moving again.

Now that I’ve come out the other side, I realize I feel more financially secure than I ever did before that dry spell.

Money in the bank isn’t enough

The first time I heard Pia’s definition of financial security, I had been divorced for a few years and thought I had successfully rebuilt my business around retainers.

I actually felt remarkably secure for a minute.

Then a great long-term retainer ended. Womp womp.

I’d made the mistake of letting one client become the majority of my income, and suddenly I had no idea where my next dollar was going to come from.

I had plenty of savings in the bank. Technically, I was fine.

But after months without income, I felt like I was teetering on a cliff. There’s a difference between normal ups and downs and not knowing when (or if) money is going to start coming in again.

But what was interesting was how irrelevant the savings felt. The real problem was not knowing if I could turn the tap back on.

I’ve been self-employed for a long time, and I know some inconsistency comes with the territory. The goal can’t really be to recreate a paycheck that arrives in exactly the same amount every two weeks. That’s called a job. (And when it’s in the form of one big retainer, I’d argue that’s basically a job without benefits.)

Savings help you weather the quieter stretches. And obviously, a longer track record of making money helps you trust that you can do it again.

But I’ve realized there’s another kind of confidence that matters even more.

Can you turn it around?

It’s one thing to have made money before.

It’s another to hit a rough patch, figure out what isn’t working, change it, and watch your pipeline fill up again.

That’s what happened to me this year.

I let things be slow for about six weeks. It was the holidays and I was happy for a little break. I took a couple of vacations and really enjoyed myself.

But I didn’t want to start the year hoping sales calls would magically pick back up. So with the help of my coach, I started looking closely at where things might be breaking down.

Taking control

So what did I change?

I got more specific in my marketing.

I sharpened the language on my website and in my newsletters around what my potential clients are actually experiencing and the problems I solve.

I also started selling more explicitly in my newsletter. Nurture-y content comes much more naturally to me, but with some coaching, I figured out how to make clearer offers while still being myself.

I removed friction from my sales process.

When I first started focusing my business on branding and web design for women service providers, I spent too much time on calls with people who just wanted a logo or expected me to compete on price with Fiverr and Upwork.

So I built in a lot of pre-screening. I listed my minimum package prices on my website and required people to confirm that they had seen those prices before they could book a call.

For a couple of years, that worked beautifully.

But the economy is different now, and a lot of people are understandably being more cautious about how they spend their money.

I could see in my website analytics that people were spending several minutes on my sales call page and then leaving without submitting the form.

So I removed some of that friction.

Almost immediately, I went from months of near crickets to booking several calls a week.

Because I was doing less pre-screening, I also worked with a sales coach to sharpen my sales process and make sure I was having better conversations with the people who did book.

Within five weeks, I booked eight new clients.

And that momentum from the spring has continued. I’m now booked into December and I only have one slot left for a full Brand Build this year.

One more important thing

While I was struggling, I really leaned on other business owners and my coaches.

I have a strong community of friends who are also entrepreneurs, and I cannot overstate how important that is.

They’re the people I cry to, bounce ideas off of and problem-solve with when something isn’t working. They’re also crucial voices of reason when I start spiraling and thinking the sky is falling. It almost never is.

Self-employment can make you feel like every problem is yours to solve alone, but you can’t operate that way. I saw something on Instagram (so we know it’s true) about how the most successful leaders are good at asking for help. I believe it.

This is the part that feels like security

I’ve been in business for more than 20 years and spent a lot of time letting my business happen to me. But since my divorce, I’ve rebuilt it into something I’m genuinely proud of.

There have been a few moments in the last few years when I’ve looked up and thought, wow — I’m really doing this and I know I can keep it going.

One of those times is now.

Because I have real evidence that when business slows down, I don’t need to know exactly where the next client is coming from. I just need to trust that I can pay attention, figure out what needs to change, ask for help when I need it, and fucking do something about it.

Goodies Just For You

WHAT I’M THINKING ABOUT: Is anyone else watching Furious on Hulu? It’s remarkably good. No big surprise, since it’s the same creator as Dying for Sex and New Girl, Liz Merriweather. She’s a freakin’ genius. I still have 2 episodes left, so no spoilers please!

WHAT I’M MAKING: On Sunday I made a big pot of this Chicken and red lentil soup that lasted me a few days. It was one of the top recipes in the NY Times last year, but a lot of comments said it was bland, so I made the following updates, which I recommend: added 1 tbsp tomato paste, 1 tsp cumin, and I subbed 6 cups of chicken stock for 6 of the 8 cups of water in the recipe (no wonder the original recipe is bland!). I also added mint and preserved lemon to the yogurt garnish. Delish!

WHO I’M ADMIRING: Katie Dunn is an angel investor, fundraising strategist, and a true expert in fundraising for early-stage founders, particularly underrepresented founders. She’s also a client who’s become a friend. She has a new Substack called The Masthead Strategy, where she’s sharing practical fundraising frameworks, what investors are actually thinking, and real tear-downs of founder materials.
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