Hi there, it’s Octavia.

So last week I told you I was building something. And today, it's here.

Imagine reaching the start of September with something real to show for the last 30 days, instead of overthinking the same idea you've been bouncing around in your mind since the new year.

I know what that gap feels like, because I've lived in it.

And that’s why I created the Wins Challenge.

I've talked a bit about how I learned to bet on myself first, but that was after a lot of trial and error. I sat on the idea for what became my first book for years. I actually tried once, and when that attempt faltered, I quietly gave up.

I only realized my mistake years later when I was invited to be part of an exhibition called Women Who Dared, in a beautiful library in Oxford, England.  

And that evening I remember so, so clearly because I felt like a fraud.

I had been invited by the curator on the back of work I’d done years prior. And I stood in that library, staring at the rows and rows of books, wondering how I could be considered a "woman who dared" when I wasn't daring to do the one thing I actually wanted.

On the flight home to Los Angeles, I decided to start over, try again to become an author, and aim to go further than my last attempt.

I already knew what hadn’t worked for me, so I needed to build a strategy that would stop me from quitting too soon again.

So I got to work. It didn't feel fast. It felt long and slow to be honest.

But piece by piece, week by week, I did the small things nobody was watching. I researched my book idea. I started learning what a book proposal should contain, and I started writing my first chapters.

All those small, quiet steps became tangible when I finally received a phone call to tell me I had been offered a book deal with Wiley.

None of that happened because I suddenly felt ready. It happened because I stopped waiting to feel ready and started stacking small, visible proof that I was moving in a direction I desperately wanted.

Betting on yourself first is the unlock that makes what follows possible.

And that's what the Wins Challenge is built to do for you.

This is the thing that I’ve been working on quietly, but it was designed to be shared. And here it is.

The Wins Challenge is a live, 30-day experience to move one meaningful professional goal from intention to action to results. It runs August 1 through August 31.

→ Join the Wins Challenge

You'll:

By August 31, you won't just have an idea you meant to get to. You'll have 10 documented wins, and proof you're someone who follows through.

In Week One, you'll clarify the goal, why it matters, and how you'll measure success.

By Week Two, you'll be building consistency and identifying what threatens your momentum. 

At the midpoint, we'll review what you've accomplished, work through your obstacles, and adjust the plan if needed.

During the final two weeks, you'll keep stacking wins.

On August 31, we'll come together to reflect on what changed, celebrate the progress, and decide what's next.

You'll walk into September with something you can't fake. A documented stack of proof that you kept a promise to yourself, and a repeatable process to keep the momentum going long after the challenge ends.

Does a 30-day challenge mean I need to work on this every single day in August?

No. This isn't about grinding daily. It's about showing up for yourself consistently enough each week to build real momentum, and rest is an essential part of that.

The challenge is designed to help you focus on the actions and mindset that get you further, not to add unrealistic pressure.

The only person you will compare yourself to is how you approached this before versus how you’re betting on yourself now.

What happens if I can't make a live coaching session?

That’s totally okay, you're covered. All three sessions are recorded, so you can catch up on your own time.

Showing up live is great, but it's not required to get the full experience. And if you have a question about your next steps, email me, I'd be happy to answer.

What if I'm not sure about the kind of progress I could make in a month?

That's exactly what the kickoff of the program is for. I'll be explaining the different types of invisible and visible wins, and you don't need to start the challenge with total clarity. All you need is a sense of the one thing that would matter most if you finally moved it forward.

The Wins Challenge runs from August 1 through August 31.

I created this challenge because I know how hard it is to do things in isolation when you're working through the messy middle.

I'll be working my own goal alongside you all month, and you'll have a cohort choosing their own goal at the same time, cheering each other on.

Right now, the Wins Challenge is available at early access pricing of $149, down from $199.

That price ends at midnight ET tomorrow, Tuesday, July 28. After that, it's $199 through the close of enrollment on Friday, July 31.

→ Join the Wins Challenge

Are you ready to finally move that one goal forward this August?

I'd love to support you if now feels like your time.

Octavia