My biggest wins, hardest lessons + what I’m taking into 2025

Written By Jessica Shirra

In This Edition

  • 3 wins from 2024 + what I'm taking into 2025

  • What I'm leaving behind and the lessons I learned (so you don't have to!)

  • If we were hanging out in my DMs this is what I'd be sending you...

A Quick Note to My Inner Circle

I’m writing this to you as I’ve just closed out my last meetings of 2024 and am heading into (not to be dramatic but…) maybe my favorite part of the whole year…

My team’s “lite mode”.

AKA – the 2 weeks between Christmas and the New Year where we’re resting, we’re recharging, we’re available to clients and reacting to anything in real time, BUT…

No meetings. Nothing net new. Lazy mornings. IF you work hot chocolate on your desk is a must. Bailey’s optional.

But as I’m writing this: one thought keeps coming to mind…

It’s tempting to just focus on the highlight reel at the end of the year.

(And don’t get me wrong…I love a good highlight reel. Or Reel. See what I did there?)

But the truth is: every year is full of a lotta highs, lows, and lessons…

So here’s a peek behind the scenes of my year – the wins I’m proud of, the challenges I faced, and the lesson I’m carrying into 2025…

My Highs, Lows and Biggest Lesson

3 Wins (Highs):

As I’m reflecting on the past year, here are our 3 biggest wins…

1. Our Biggest Year Yet
​2024 was our biggest year to date – I doubled my revenue in a year when so many businesses struggled to grow or even maintain what they hit in 2023.

Two things made this possible:

  • Referrals: Some of our best clients came from referrals this year. It’s hands-down my favorite growth strategy because referral clients come in with built-in trust (and like attracts like—so they’re usually a dream to work with). I’m leaning BIG into this for 2025.

  • Growing my Team: Scaling wasn’t happening without help, so I grew my team this year—strategically and carefully. I brought on another incredible CMO, which allowed us to take on more clients, and added a few new subcontractors to deliver high-quality execution for our clients. I’m so proud of this small but mighty team.

(Speaking of team: meeting Cheyenne IRL for our strategy retreat was such a highlight!)

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2. Overcoming Client Challenges with Integrity
​Not every client relationship was smooth sailing this year. But one of the things I’m most proud of is how we handled the hard stuff.

We’re BIG on accountability here. I call it “radical responsibility”, so we spent a lot of time reflecting:

  • Where could WE have been better?

  • What parts were for the client to own?

Those reflections have led to some big shifts:

  • Refining our packages and strategy development process.

  • Getting even clearer on our ideal client profile—because the right clients and teams make all the difference.

The takeaway? Challenges can be your greatest opportunities for growth if you’re willing to face them head-on.

3. A Year of FUN and Connection
​Personally, 2024 was filled with moments I’ll never forget:

  • I saw Taylor Swift’s Eras Tour TWICE with my best friends. Enough said.

  • Craig and I celebrated our 10-year wedding anniversary in the Bahamas—a bucket list trip that was pure magic.

  • I hosted a girls’ weekend at my place this summer, spent countless pool days with family and friends, and watched my little ones start kindergarten and preschool (cue the tears).

We also tackled a HUGE outdoor reno with fruit and veggie planters, meandering stairs, and peach + cherry trees. Gardening with my girls this summer? Pure joy.

Family trips, first-time skiing and camping adventures, rock climbing (a hit for Ella, not so much for Blaire ), and deepening connections with new and old friends—this year really leaned big into my value of connection.

3 Challenges (Lows):

1. Knowing When to Walk Away
​This year, I learned the hard way that sometimes the best thing you can do—for the client and for yourself—is walk away.

I remember the exact moment I knew we’d lost a client’s trust. Her business wasn’t doing well, and instead of trusting our expertise, she doubled down on what worked in the past (even though we knew it wasn’t working now).

I stayed way too long, trying to turn things around while running into hurdle after hurdle—lack of executional support, poor quality work, and a breakdown in trust.

The lesson? Next year, I’m trusting my gut sooner and letting go of relationships that no longer serve either side—with care and integrity.

2. Getting Clear on Expectations
​Sometimes, I let my clients’ goals drive what we were doing—when I should have stepped in and said, “That’s not realistic.”

One client wanted to stop launching (their main revenue driver) but still double their revenue. Make it make sense!

The learning here is simple but powerful:
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​It’s my JOB to set clear expectations, guide my clients, and be the advisor they hired me to be—even when those conversations are hard.

^Put that on a sticky note when times get tough.

3. Saying Yes at the Expense of My Priorities
​Saying yes to too many clients and projects came at a cost:

  • Creative time for content I love creating.

  • Meeting-free Fridays for deep work.

  • Time to work on my business—to nurture my team, improve processes, and step fully into my CEO role.

I felt stretched thin and found myself craving space—space to think, to create, and to focus on the things that move the needle.

Next year, I’m doing things differently:

  • Tighter boundaries around my time—and actually holding them.

  • Taking on fewer, highly intentional Fractional CMO clients.

  • Expanding into advisory and lighter-touch work, where we can still deliver big-picture strategy and results without being embedded day-to-day of our client’s businesses.

This shift gives me the space to focus on creativity, growth, and the bigger vision for my business.

The Big Lesson: Don’t Focus on the Gap, Celebrate the Gain

This year, I hit what once felt like a crazy revenue goal, grew my team, and still made space for life—the family trips, the friendships, and the personal milestones.

But here’s the thing: It’s easy to focus on the gap—what didn’t go right, where you fell short, or what you still want to achieve.

What I’m carrying into 2025 is this:
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When you focus on the gain—what you’ve done, how far you’ve come, and the progress you’ve made—it changes everything.

Growth doesn’t always feel dramatic or perfect. Sometimes it’s steady, incremental, and quiet. But it’s happening, and when you measure the gain, you see just how far you’ve really come.

Your Turn

If you haven’t done your own year in review yet, take 10 minutes today:

  • What were your 3 highs?

  • What were your 3 challenges?

  • What’s the 1 big lesson you’re taking into 2025?

Trust me—it’s worth it.

And if you’re ready to set yourself up for your best year yet, stay tuned. I’ve got BIG things planned for 2025, and I can’t wait to share them with you.

Hit reply and tell me: What’s one thing you’re proud of from this year? I’d love to celebrate it with you.

Want to Work Together?

If you’re ready to take your marketing to the next level + grow your CMO business, here’s how we can work together…

Bring NAVI In As Your Fractional CMO: Unlock a custom marketing strategy to elevate your brand (+ your revenue) in 2025. Work with NAVI.​

Enroll In Fractional CMO School: Join my six-month coaching program + community designed for marketers who want to attract aligned clients + build their dream business as a Fractional CMO. Learn more and enroll.

Jessica Shirra