Try it again (please)

The ones that didn't work birthed the ones that did

Dec 02, 2024

The Sustainable Solopreneur is a weekly newsletter about seasonal, cyclical, supportive business strategy for solopreneurs and creative souls who want more out of life than the status quo, hosted by business coach and strategist Jenni Gritters. If you’ve been reading this newsletter for a while and you receive value from it, I’d encourage you to sign up for a paid subscription.

I’m hosting another round of small group coaching pods! This round will happen in December and January, and will be focused on year-end reflection and 2025 planning. If you’d like to try out coaching with a small group of solopreneurs matched to your unique challenges and focus areas: This is for you! These are so, so fun (and highly productive). New biz buddies + a biz strategy for 2025, coming right up.

Join a squad

In January 2024, I offered my first-ever workshop on my own. It was a 4-week intensive, priced at around $400, focused on the psychology of small business ownership.

I posted it on social media and… no one signed up. Then I sent an email about it… and no one signed up. I panicked and eventually, without a lot of fanfare, I shut it down.

A month later, I relaunched the same program as a one-hour, $29 workshop. I realized that the pricing was too high on the initial offer (for my audience), so I reframed it to focus on the mindset you need to bring in new clients, making something that seemed “squishy,” more concrete. That time around, things went much better. 15 people signed up and I was able to practice a curriculum I now teach regularly. Still, it took three weeks of marketing emails and many social media posts to get to 15 attendees.

Last week, about 11 months after my first workshop launch, I offered a workshop (in partnership with Lettuce — you can download the recording here for free). After just two emails, 175 people signed up. And that’s no accident.

Why? Because I’ve learned a lot from launching programs all year and watching them fail. As I told someone in my group program, SUSTAIN, last week: You can’t iterate on something that doesn’t exist!

Here’s another example: Over the past few years, I’ve offered so many versions of my 1-1 coaching programs. At times, I’ve felt massively frustrated about not being able to get it right. Yet, each time I tried something new, I learned a lot. Here’s the timeline:

The first version of my 1-1 coaching program was a “book whenever” model. It was a little like therapy: Book a session whenever you need it, with a self-booking link. People loved this model but it made my revenue impossible to predict and there were tons of cancellations.
Next, I switched to 4-packs of sessions. These sold well but again, the scheduling was a problem. They were still chaotic for my calendar because I didn’t have appropriate boundaries set around how people could use them. I couldn’t plan ahead for how many openings I would have available each month.
Then there was a mastermind I launched, then folded, called the Sustainable Scale Club, which included 1-1 coaching and group time. But, as I wrote previously, I felt like this program wasn’t aligned well with my mission or my capacity. Four people signed up and I refunded them when I closed the program after a few weeks of marketing.
There was also a more expensive VIP package, priced at around $1000/ month, that I only sold to two people. The price point felt too edgy for the people I met with in free business audits, so they weren’t selling.
Finally, about 4 months ago, I landed on PLAY, the version of 1-1 coaching I have now. It’s the right price ($850/ month) with the right scope (unlimited Voxer coaching, one strategy session per month and a small group call). And it has been selling really (really!) well.

Do you see how many versions of these programs and workshops didn’t work before I landed on one that did? That’s normal! So normal!

Hear me when I say this: If you’re on workshop number 1 and it feels like no one is signing up, you’re not doing anything wrong. If you’re on workshop number 5 and it feels like there’s still some tension whenever you market it, you’re not doing anything wrong. And if you launch your offer to the world to crickets, or even book some intro calls but no one is converting, you’re also not doing anything wrong.

This is how it works to run a business, my friends.

There is no way to land on The Thing That Works without doing a lot of Things That Don’t. Each time you launch an offer or send a pitch, you’re learning. My first workshop was far too expensive for my audience — and I couldn’t have known that if I hadn’t actually launched it! My first 1-1 coaching offer was too chaotic for my calendar — but I also couldn’t have known that if I hadn’t actually asked a few people to work their way through it.

I’ll say it again: You cannot iterate on something that doesn’t exist.

Many you are sitting on incredible ideas that you’re too afraid to launch because you know they’re not perfect. Or you’re sitting there thinking and thinking and thinking about how to create The Thing That Works. But the truth is that there’s no way to make an idea perfect enough to guarantee that you’ll avoid the whole process of iteration and resetting. The only way to make a Thing That Works is to try stuff, over and over again

My coach, Amber, often reminds me that it’s about the reps.

It’s a great metaphor: Think about going to a soccer game and expecting that you’re going to score a goal the first time you step onto the field. That would be ridiculous, right? What you might expect instead is that five months of practicing kicking the ball into the net and lifting weights would make you more likely to score that goal.

And that’s what I’m reminding you of today, too: Put in the reps. Expect to learn. Know that it all won’t work. But know that by trying, you’re moving closer to the ideas that will work. You’re honing in on who your audience is, what they need, and how you can best help them.

Listen to the feedback! And don’t be afraid to be seen trying. As Brene Brown would say: Those who aren’t in the arena with you, don’t get to judge.

My group coaching program, SUSTAIN, is focused on helping you get that first iteration of your big idea out of the gate: The new offer, the coaching program, the newsletter, the podcast, the business model that actually works, the pricing that feels edgy but is necessary, the strategic pivot. We sit in that room and support each other as we try and fail and learn. We learn together. Which, in truth, is the only way I know to make this whole process easier!

You're invited to SUSTAIN

The question, today: What are you holding back on, because you’re afraid it won’t land perfectly?

Let it fly.

Jenni

Curious about my background? I’m a writer and business coach living in Central Oregon. My goal is to teach everyone who will listen that it’s possible to build a simple, stable, successful business that support your human needs first. Join my group coaching program, SUSTAIN, for more conversations like this (and a community of people who are all about the path less taken), and follow me on LinkedIn or Instagram.