The Messy Middle
What Happens Between the Big Decisions Matters More Than We Think
We love to tell our stories in clean arcs: the leap to a new role, the launch of a company, the big life decision that looks linear in hindsight, all of life and love. But real life doesn’t move in straight lines.
Between each headline moment lies what my dear friend Tiffany Haynes has called the messy middle — the stretch of time where nothing is quite decided yet. It’s the in-between: between jobs, between relationships, between titles, between identities, between what was and what’s next.
If you’ve ever sat in that space, you know it’s equal parts liberating and disorienting. Your calendar is suddenly wide open. Your inbox quiets down. Your phone isn’t ringing as often. You’re left with a lot of time to reflect on who you are without the nameplate or the title.
Those that really know me, know that I pour all of myself into everything I do — whether it’s building something from scratch, leading teams, or showing up for the people I care about. So when a chapter ends, it doesn’t feel like simply flipping a page. It feels like a quiet room that used to be full of music. Sometimes the silence is deafening.
The last few days I had the opportunity to spend many hours on the road (hello, time off roadtrips), and listen to some of my favorite songs. One that particularly stuck out to me over the weekend was when Jewel sings “You Were Meant for Me,”
“Dreams last so long, even after you’re gone.”
That lyric has always landed with me, but this week it felt extra impactful. It captures that bittersweet sensation of carrying the weight of a dream — or a role, a love, or a season — even after it’s technically over. In the messy middle, those echoes can be loud.
[If you’ve never heard this song, it’s about the bittersweet, lingering feelings after a breakup, where she reflects on an ended relationship that she still believes was fated.]
The Voices Around You Shape the Next Chapter
In these liminal spaces, something subtle happens: the voices of the people around you get louder. Friends, mentors, colleagues, even casual acquaintances — everyone has thoughts about what you “should” do next.
“Take the stable option.”
“Swing bigger.”
“Don’t lose your momentum.”
“You’d be crazy to leave that.”
Sometimes these voices are supportive. Sometimes they’re fearful. Sometimes they’re well-meaning but rooted in their own insecurities. If you’re not intentional, their voices can start to write the next chapter for you before you’ve had the chance to decide what you actually want.
In fintech and banking — industries that prize decisive action and clear strategy — ambiguity can feel uncomfortable. We’re wired for execution, not always incubation. But the truth is, clarity isn’t something that strikes like lightning. It’s something that emerges through quiet reflection and intentional conversation with people who know your heart as well as your resume. Only through intentionality can you find clarity, I truly believe.
Curating the Circle That Holds You
I’ve learned that what transforms a messy middle from chaotic to catalytic is who you choose to keep close during that time.
The friends who ask better questions instead of rushing to give answers.
The mentors who remind you of your values and vision, not just your accomplishments.
The peers who sit with you in the uncertainty without flinching.
The ones who lovingly call you out when you’re shrinking to fit someone else’s idea of “safe.”
The loved ones who hold your hand and sit in the silence with you when needed.
This isn’t just emotional support (although again, if you really know me, know I need this most of all :) ). Just as a startup curates its board, curating your circle during the in-between moments determines the quality of your decisions. It’s the difference between chasing momentum and choosing alignment.
The Messy Middle in Fintech
This theme plays out everywhere in our industry:
Founders between Series A and B, wondering if the original vision still fits.
Executives stepping away from legacy institutions, notebook in hand, ready to chart something new.
Operators deciding whether to return to corporate comfort or build something from scratch.
These are not professional crossroads, but they’re deeply personal recalibrations. And yet, they’re rarely talked about publicly. We celebrate the big announcements, not the quiet in-between where the real decisions take root.
Embracing the In-Between
The messy middle is uncomfortable because it demands honesty — about who you are, what you want, and who you trust to walk alongside you. But it’s also where the truest next chapter gets written.
For me, I’ve learned to honor this space. To let the room (and my brain) be quiet for a bit. To listen to the lyrics that linger (in this case, thank you Jewel). To surround myself with people who remind me not just of what I’ve done, but of who I am and who I want to be.
When the next announcement comes, the world will see a clean headline. But I’ll know: it was the messy middle — and the voices and people I let in — that shaped everything. 💜
Thank you, as always, for your support. And, most of all how you do it with so much heart. Can't wait to see you next week in Vegas. XXOO