Don’t go through a career transition alone.

We help experienced leaders process change, anticipate surprises, regain confidence, and explore what comes next with a trusted peer group and 1:1 support, because career should be a team sport.

Book a discovery call

Founding cohort forming now. Runs Sept 14 – Nov 5 in Boston. Limited to 8 seats.

Why this exists

Career transitions are especially difficult for experienced leaders, because the social and emotional hurricane that accompanies a shift is almost never forecasted.

The problem isn’t how anyone got here. It’s that once you’re in-between, there’s almost nothing built to support you. Not for the way careers actually work now.

In this moment, people often grapple with uncertainty, shame, blame, anger, fear, guilt, loneliness, overwhelm, shattered confidence, countless micro-disappointments, and a lack of self-compassion.

Afternoon Harbor is our answer to this challenge.

Don't stay in your silo and race to the next thing like we've all been trained to do.

Move your career forward with the support of a team and a safe space to strategize.

Brady Sadler, founder of The Afternoon Shift

Hi, I’m Brady.

Creator & Lead Advisor

I've been through two major career transitions myself. The first was packed with experiences that caught me completely off guard. The second time I went in asking questions, and I heard the same story from nearly everyone I talked to. Loss of identity, shame, loneliness, and a lot of people doing their best to stay in "performance" mode, whether they were in a job or in between.

Harbor is my effort to build the kind of support we need in the most difficult point in our career.

I've spent 25 years in marketing, media, and entrepreneurship, building all-star teams and award-winning shows and campaigns. I'm also the author of Collaboration Is King.

Today I consult with global brands and I lead The Afternoon Shift, where I've hosted events with hundreds of leaders and written 70+ essays about the changing nature of work.

MISSION: to help business leaders flourish in mid-career by finding meaningful work and long-term collaborators.

Who It’s For

Afternoon Harbor is a peer-based group program for experienced leaders who are in a career transition.

You’re likely a fit if you have 15+ years of work experience, live within driving distance of Boston, and one of these is true:

- Just left a leadership role
- Currently negotiating your exit
- Anticipating a change
- Independent or consulting, but missing a team
- Returning after a deliberate break
Our Core Values:

Candor
Kindness
Curiosity
Generosity
Collaboration

The Founding Cohort Experience

Eight weeks, six in-person experiences, four 1:1 advisory calls, ongoing alumni perks.

01
September 17 · Cohort Meeting 1  
Our first "Harbor Hours" will be held at 10 Derne, former site of the Yale Club in Beacon Hill. Meet your founding teammates, learn from guest experts, build clarity, and begin to chart a new path forward.
02
September 24 · Field Trip
Our host is Ama, the new restaurant concept from the founders of the award-winning Comfort Kitchen. Enjoy a special prix-fixe lunch (included), and network with generous leaders from the larger Afternoon Shift community.

Bonus: optional "Harbor Hours" with your cohort before and after the lunch.
03
October 1 · Cohort Meeting 2
Our second "Harbor Hours" cohort session takes place at Shy Bird in Fenway. Join a collaborative session with a guest advisor, and spend time problem solving with your new team. Access to second screens, printing, and other perks. Lunch and bottomless coffee included.
04
October 8 · Cohort Meeting 3
We gather once again to continue learning, sharing, planning, and tracking our progress.

Guest experts and location coming soon.
05
October 22 · Field Trip 2
Our second opportunity to engage with the wider community of leaders, aka Shifters, plus a special activation with VDOP Café - one of Boston's hottest pop-up coffee concepts - and a little friendly competition.

Venue details forthcoming.
06
November 5 · Cohort Meeting 4
We celebrate our progress, name what’s next, and recommit to helping each other as we go from founding cohort to founding alumni.

PLUS:
‍
• Four 1:1 calls with Brady
• Expert Chats (virtual masterclasses with superstar guests)  
• Lunch at every in-person gathering
• Concierge networking support and roadmap
• Personal branding audit and content creation advising
• Guest appearance on The Afternoon Shift podcast (share your expertise)
• Copy of Seth Godin’s new book, The Knot
• Complimentary pass to the 2nd Original Signal Salon conference in Boston - Fall '26
• Harbor perks:
- Launch by Lunch AI workshop discount
- More coming soon

Scruffy networking: connection without the need to perform.

Up to now, Field Trips have been the core of The Afternoon Shift: creative leaders, creative spaces, and none of the usual pressure or networking theater.

Now, Field Trips are also a key element of Harbor. Founding cohort members will experience creative spaces around Boston and network with generous leaders from outside of the core group.

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FIELD TRIP ATTENDEE

“Yesterday felt like walking into an oasis of positivity and talent and support.”

FAQs

Is this therapy?
Is it confidential?
What does it cost?
I'm employed but see change coming. Can I join?
How is this different from career coaching?

The next chapter starts with a conversation.

Begin the process

Founding cohort forming now. Runs Sept 14 – Nov 5 in Boston. Limited to 8 seats.