Productive Flourishing

To be a leader means managing constant complexity. Shifting priorities, team dynamics, capacity challenges, and the pressure to execute while everything keeps changing.

Our Leadership Strategy Sessions are supportive, no-fluff monthly virtual meetings for leaders navigating the real challenges of modern team life.

Each session blends practical guidance, coaching, and peer Q&A. We tackle what’s most timely and relevant, from clarifying team roles and managing capacity to leading through change and building trust.

You don’t need to prep. You just need to show up as you are, with whatever’s on your plate. These sessions are designed to meet you where you are.

The annual plan you built in January was based on what you knew then. Six months in, some of that picture has held. Some of it hasn’t. And right now, while the pace is slower and the team is in and out, it can be hard to notice what’s shifted.

But it’s there. Projects that have stalled without anyone naming them stuck. Work that’s functionally done but never properly closed out, still generating quiet friction. Initiatives that were deprioritized months ago but are still showing up in status updates because nobody’s said out loud that they’re off the table.

July is a good moment to look at what’s actually on your team’s plate against what the annual plan says should be there, and make some deliberate decisions before September makes them for you.

We’ll explore themes like:

• Telling the difference between what’s truly active and what’s just still on the list

• Naming stuck or dead work out loud so the team isn’t carrying it in silence

• Closing out work that’s done but still creating friction

• Deciding what belongs in the back half of the annual plan and what doesn’t

Bring questions about: Where your team’s annual plan has drifted from reality, projects that are stuck or dropped but haven’t been named that way, how to have the conversation about what’s no longer in play, and what a deliberate mid-year realignment looks like in practice.

These monthly calls are part of a paid/premium subscription to Productive Flourishing. 

If you’re not a premium subscriber yet, I encourage you to upgrade your subscription and join us Wednesday, July 1, 2026, at 11:00 a.m. PDT.

Paid subscribers, here’s what you need to know to join the call:

🌟 While we no longer record the Q&A discussions during our Leadership Strategy Sessions, we continue to record the opening teaching. Enjoy a special preview of what we shared about leading when energy shifts and structures loosen. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next month.

Last month we focused on getting ahead of the summer shift. Now we’re in it.

The leadership work of this season comes down to one thing: expectations. What kind of season is your team actually in? What are you maintaining, and what does that work look like when it’s done well? What behaviors and outcomes are you solving for between now and September? Get those answers out of your head and in front of your team before July gets slippery, and resist the pull to force this season into something it isn’t shaping up to be.

That thread ran through the entire session, from the teaching to every Q&A conversation.

This month’s Q&A also covered:

• Whether to plan around quarters or semesters, and how to choose the frame that matches your actual energy cycles without creating extra translation work

• Reframing a season of lower business output as intentional investment in relationships and network-building, rather than evidence of falling behind

• Why being intentional and being transactional are not in conflict, and how confusing the two gets in the way of showing up authentically in relationships

• ...

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Our May tips talked about choosing the cadence that works best for you. Maghan shared how she’s experimenting with semesters instead of quarters, because that feels more energetically aligned to where she is, and where her transition points are between her yearly “seasons.”

I realized (again) in my haiku practice, after each piece explored themes of change, that I’m deep in a transition of my own. I touched on this in April’s tips, where I was feeling the restless energy of spring and that sense of a change on the horizon. But in the past couple months, that feeling of transition has intensified.

As Mom’s dementia journey has created changes for her, my role as caregiver has changed, too. From the last several years where I was the primary “doer” of Mom’s care, to this transitional phase where I need help helping her, to (very soon now) a time when Mom’s care will be entirely in the hands of professionals.

All of which has me thinking about transitions and changes and the labor required of them, and how that relates to seasons of building/growing and maintaining/resting we’ll be touching on in June. I’m reminded that transitions, whether personal or organizational, often require elements of both: of maintaining what’s critical while simultaneously working on the core project(s) that represent the change.

Sometimes that change project requires intensity and growth energy, a strong plan and concerted...

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Most people treat email like it’s the easy part of the day, but it’s sneakily one of the more taxing things you might do.

When you scroll social media or read an article, you’re consuming. It’s a low-obligation, low-consequence activity because you usually don’t have to decide anything, respond to anyone, or track a single open loop.

When you write a proposal or work through a strategy doc, you’re producing. It’s high effort but coherent, with one context, one goal, and one thread to hold.

Email is neither of those things.

Every message you open starts a sequence of context and content shifts. You figure out who this person is and what they actually need. You decide what the right response is — and often, whether now is even the right time to give it. Then you write it in a way that moves things forward.

And then you do it again, with a different person, a different project, and different stakes, sometimes within the same minute.

Most of those decisions resolve in seconds. Newsletters can be skimmed or archived, meetings can be accepted or declined, and (truly) quick questions can be answered quickly.

That’s genuine admin work, and it’s what admin blocks are built for.

But a small segment of emails can’t be resolved that way. They’re the ones that trigger “okay, I need to actually think about this one.” Back in 2009, I called these Jumbos, but...

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🌟 Enjoy a special preview of this month's call replay! We're sharing a clip from our opening conversation on mapping your personal energy cycles and why the calendar you're using might be working against you. If you're not already a paid subscriber, consider upgrading to access the full recording and be part of upcoming sessions.

Thank you to everyone who joined our May Monthly Momentum Call!

There is a moment in May where you start to feel it. The rhythm that carried you through spring begins to shift. Energy changes, the summer stretches out ahead, and the months to come look and feel different from the ones behind you. (And for those of you in the southern hemisphere, the same is true as you move into winter and your own seasonal shift takes hold.)

This month, we explored what it actually looks like to plan around your own seasonal energy rather than defaulting to a calendar that wasn’t designed with you in mind. Our OpTempo Wheel worksheet was built for teams, but it turns out it’s just as useful for mapping the natural rhythms of your own year. Plotting your energy across 12 months makes the patterns hard to ignore, and might have you asking the same question it raised for us:

What if your planning year started when your energy peaks, not when the calendar says to?

Here are some of the other topics we explored this month:

• Timing a creative relaunch around life transitions: How to think about when to restart a project you’ve been sitting on, when...

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May was about looking honestly at what you, your projects, and your team could actually hold between now and September. Reading your OpTempo (operational tempo) before the season arrived rather than discovering it when something dropped.

June is where that work has to translate into how you actually work.

Not everyone arrives in June in the same season. Some teams have real energy right now and meaningful work that matches it. Some individuals are in a genuine growth stretch. Others are in something slower, a season that calls for maintaining rather than building, tending what’s already in motion rather than launching what’s new. Both are legitimate. Neither runs itself.

The harder truth is that the seasons requiring more deliberate leadership (for your team or yourself) aren’t always the ones with the most energy. Knowing what season you’re in is only half the work. Leading yourself or your team well during a slower season without defaulting to building-season expectations or letting the slower pace become drift, is where the real skill lives.

This month, both our Leadership Strategy Session and Monthly Momentum Call explore what it looks like to lead well in the season you’re actually in.

We hope to see you in June! (Details below 👇🏽)

For leaders navigating team dynamics, organizational priorities, and the challenge of maintaining sustainable momentum while delivering results.

Read more here... »

Our Monthly Momentum Calls are designed to help you focus on what matters most, offering a supportive space to clarify goals, overcome challenges, and make meaningful progress — whether you’re pursuing a creative project, growing your business, or balancing life responsibilities.

Each 60-minute session blends teaching, hot- support-seat coaching, and interactive Q&A, providing real-time support and actionable insights to help you move forward with clarity and purpose.

You came into May with a question: what does this season actually have room for? Maybe you have some version of an answer now. Maybe it confirmed that this is a real growth stretch for you and your projects. Maybe it revealed something slower, a season better suited to sustaining than expanding.

What neither answer comes with is an instruction manual for how to work well within it.

A growth season without enough structure scatters. A slower season without enough intention drifts. The work in June is learning to lead yourself skillfully, making real progress on what the season can actually hold, and resisting the pull to measure that progress against a season you’re not in. Part of that is seeing the season clearly, including the projects that summer quietly adds to your plate that never make it onto your official list.

We’ll explore:

• What working well actually looks like in your season, whether that’s growth or...

Read more here... »

To be a leader means managing constant complexity. Shifting priorities, team dynamics, capacity challenges, and the pressure to execute while everything keeps changing.

Our Leadership Strategy Sessions are supportive, no-fluff monthly virtual meetings for leaders navigating the real challenges of modern team life.

Each session blends practical guidance, coaching, and peer Q&A. We tackle what’s most timely and relevant, from clarifying team roles and managing capacity to leading through change and building trust.

You don’t need to prep. You just need to show up as you are, with whatever’s on your plate. These sessions are designed to meet you where you are.

For most teams, June marks the beginning of a slower stretch. Not a stopping point, but a season where the work shifts: maintaining progress, holding focus through looser structures, and keeping what matters moving without the natural momentum that higher-energy seasons provide. That’s a different kind of leadership challenge, and one that’s easy to underestimate.

When the pace slows and structures loosen, teams drift unless someone is paying attention. Work that felt clear in April gets muddier. People fill the space with whatever surfaces rather than what matters. And leaders who keep applying building-season pressure to a team that isn’t resourced for it create a different kind of problem: one that shows up in September, not June.

The leaders who come out of summer with their teams intact are the ones who took this season seriously on its own terms. That means knowing which parts of your team are genuinely in tending mode and which have more to give, protecting the work worth protecting, and leading in a way that sets up a strong return rather than just surviving the months in between.

We’ll explore themes like:

• What deliberate leadership looks like when energy is lower and structure is looser

• How to hold your team’s focus without imposing pressure the season can’t support

• Distinguishing between what needs to be maintained and what can genuinely flex

• What you’re building toward, and how to lead now in a way that sets up what comes next

June rewards the leaders who take a tending season seriously. That’s what we’re working on.

Bring questions about: Keeping the right work moving when energy is uneven, how to hold team focus without over-managing, what to protect and what to genuinely let flex, and how to lead through summer in a way that sets your team up well for the return.

These monthly calls are part of a paid/premium subscription to Productive Flourishing. 

If you’re not a premium subscriber yet, I encourage you to upgrade your subscription and join us Wednesday, June 3, 2026, at 11:00 a.m. PDT.

Paid subscribers, here’s what you need to know to join the call:

🌟 While we no longer record the Q&A discussions during our Leadership Strategy Sessions, we continue to record the opening teaching. Enjoy a special preview of what we shared about reading your team's energy before summer makes everything more complicated. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next month.

Your team’s capacity is already shifting. The question is whether your expectations are shifting with it.

The back half of May is full of personal projects that don’t get counted as projects. School schedules changing, summer plans getting made, family logistics kicking in. All of that sits on top of the work. And when leaders keep expecting a level of output that no longer matches what their team actually has to give, that mismatch is where the anxiety lives.

This month we focused on getting ahead of that gap: getting honest about what your team’s energy actually looks like between now and September, communicating your expectations clearly, and not waiting until something drops to have the conversation.

This month’s Q&A also covered:

• Assessing your team’s summer operational tempo and communicating expectations before the mismatch creates anxiety

• Bridging the gap between monthly goals and daily focus blocks when priorities compete for your attention within a single work session

• Leading during a difficult team transition, with a reminder that tension is not...

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I was walking to the coffeeshop recently and I misread a message written in chalk on the sidewalk:

I saw “Embrace Near Misses” before my brain read “Embrace New Memories.”

As I acknowledged the misread, I realized something: “Embrace Near Misses” is not something most people would say.

But it is something I would think and say.

I’ve had a lot of these kinds of near misses in my life, from bullets to wrecks to plane flights to missed proposals.

Some of those near misses were outside of my direct control. In those cases, embracing near misses amounts to being thankful about what didn’t happen and examining what I did that may have made that near miss more likely.

Thinking of my deployment, I couldn’t control if insurgents were preparing to ambush convoys along the routes we were driving; all I could control or influence is timing my convoys road time for when attacks historically were less likely. There were too many occasions where the convoy before or after us got hit. Whether it was smart tactics, dumb luck, or Providence, I knew to embrace the near misses.

Some near misses, like my non-proposal to Angela in Greece during our college European backpacking trip, were under my control. Even though we both knew the time was right and what the answer would be, I let my brain get in the way. I didn’t have a ring. I wasn’t sure I...

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