The Second First Retreat
A retreat built entirely for the operators, integrators, and Seconds-In-Command who keep entrepreneur-led companies running.
This is for you — the whole you.
You keep everything running. You make the entrepreneur look good. You hold the culture together.
When was the last time someone invested in you?
You're extraordinary at your job. And the better you are at it, the more invisible it becomes. The best operators make everything look effortless — which means no one notices how much you pour into your role.
You might not even notice that you put yourself on the backburner a long time ago.
This retreat exists to change that.
This is for you if…
you recognize yourself in any of these.
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You can articulate exactly what your company needs. You struggle to articulate what you need.
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You feel the role (and entire business climate) changing underneath your feet and want clarity on what it's becoming — and what it means for your future.
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You're navigating a relationship with an entrepreneur that no job description can capture, and no one around you really understands.
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You've spent years executing someone else's vision brilliantly — and then wonder what your own looks like. You can't remember the last time you had a “five year plan”.
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You're good at your job. You just want to be reenergized by it again. You're not sure you'd call it “burn out”, but you're missing that “lit up” feeling.
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You're ready to be in a room where everyone gets it — hear what problems they're solving and what new ideas they're implementing.
This retreat is built around three deep, honest, and carefully designed working sessions, each focused on a different dimension of who you are as a professional and a person.
You'll leave with the kind of clarity that changes how you show up as an executive on Monday morning — how you show up for your entrepreneur, with your team, and with yourself.
01
Redefining Your Role
The job you were hired for and the job you actually need to do right now are not the same thing. The same is true for entrepreneurial businesses, as a whole.
This session gives you a sharper, more powerful identity for where the operator/integrator role is going — and what it means to be a true partner to the entrepreneur you serve.
02
Owning Your Visibility
Your success is often measured by what doesn't happen. Crises averted. Entrepreneurs freed up to lead. This session tackles the invisibility tax of being the person who holds everything together, and gives you the language and tools to make your contribution tactfully visible and known — to your entrepreneur, your team… and yourself.
03
Leading From a Full Cup
The most effective Seconds-in-Command aren't just operationally excellent. They know who they are outside of their entrepreneur's vision. They've done the work of separating their identity from their role, and they've learned the art of pouring into someone else's dream without abandoning their own. You'll leave with a personal framework and newfound clarity towards being a balanced & fulfilled executive.
The Agenda
September 21-23, 2026 | Nashville, Tennessee
Monday, September 21st
Arrival & Check-In
Ease into the retreat by checking in your room at the Virgin Hotel on historic Music Row.
Casual Welcome Reception
Join us Monday evening for a rooftop welcome reception with fellow attendees and friends of Second First at the hotel: the perfect way to arrive to Day 1 already connected.
Tuesday, September 22nd
Pillar One: Redefining Your Role
A facilitated session on what the Operator/Integrator role is becoming, the entrepreneur partnership dynamic, managing a team of other leaders, and how to confidently lead, with high impact, in all roles.
Pillar Two: Owning Your Visibility
This session names the visibility problem in your role and gives you language, frameworks, and peer perspective for how to make your contribution visible without undermining the “quiet competence” that makes you great.
Group Dinner in Downtown Nashville
Relaxed group dining to continue to connect, exchange ideas, and let the day settle. The best conversations of the retreat happen here.
Wednesday, September 23rd
Pillar Three: Leading from a Full Cup
A workshop crafted for someone whose role is defined by service, execution, and behind-the-scenes work of making someone else's vision a reality. What does it take to sustain that ambition over the long arc of a career without burning out, checking out, or losing sight of what matters most to you personally? You'll leave with a framework, a direction, and a renewed sense of what your own version of success and fulfillment looks like.
Closing & Commitments
Name what you're choosing to pursue, protect, or implement leaving our time together, and how to find support and accountability going forward.
⭐After the Retreat
1:1 Integration Call with Megan Long
Following the retreat, schedule a private one-on-one with Megan Long to integrate the retreat into your real life. Build in accountability, clear next steps, and your action items to enter your new professional era.
The Venue
Experience the real Nashville, Tennessee at Ampersand Studios, located on
historic Music Row.
Details on hotel accommodations, included in your registrations, will be sent after registration. Your room will be booked on your behalf by the Second First team at the Virgin Hotel, a short walk from our venue!
The Investment
Early-Bird Pricing until June 15th
$2,897
$3,497
paid at registration • hotel accommodations included
Rooftop welcome reception
2 night hotel lodging included at Virgin Nashville
1.5 Days of programming at the stunning Ampersand Studios
Expert guest speaker workshop
Private Group Dinner in Nashville
Printed workbooks & additional value-add surprises for attendees
Catered breakfast & lunch
Post-retreat 1:1 integration call with Megan Long
Questions? [email protected]
or schedule a Discovery Call.
Office: (615) 639-1497
Hear Directly From Past Attendees
“You'll get more out of these two days of meeting face-to-face than you can in any other meeting.” – Greg Welch, 2025 Attendee
Being in this room, being with people like you who will be able to challenge you and accept you and support you at the same time is just it's a gift.
BERGEN COOPER
PAST RETREAT ATTENDEE
I have learned so much in a short amount of time – the experience and the value I'm going to bring to the rest of my business and the rest of my people is incredible.
Kory Thompson
PAST RETREAT ATTENDEE
I've worked with other coaches and attended other conferences. What drew me to Megan first was the genuine connection…knowing there was someone in my corner to listen, advise, and guide me toward the answers I needed.
ANGELICA VALDIVIA
PAST RETREAT ATTENDEE
2026 Sponsors
2026 Sponsorship small business & corporate packages available.
Contact [email protected] for information.
Created by someone who was the Second-In-Command.
Megan Long spent a decade as the COO and Second-in-Command of a $10 million entrepreneur-led company. Even with an MBA and CPA, she spent years figuring it out on her own — isolated, without peers who truly understood the role.
Through trial, error, and a lot of long hours, she built an incredible partnership with her founder and moved the business forward. Along the way she earned a few awards — 40 Under 40, Stevie Woman of the Year, Nashville Emerging Leader. And she still felt completely alone.
Talking to other COOs, she learned she wasn't the only one. Everyone was struggling to understand their CEO. Everyone was burnt out. Nobody had built anything for them.
So she did. Second First® exists because the Second-in-Command deserves the same investment, community, and support as the entrepreneur they work alongside.
