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“Hey – So what do you do?” Why is it that we always default to work when we get this question. its like many of us have let our jobs become the center of how we see ourselves. This slowly happens to many of us, as work occupies more mental and emotional space.

I asked 50 people in martech and operations how they stay happy under sustained pressure. 

This 3 part series – titled “50 Operators share the systems that keep them happy” explores each of these layers through the lived experience of operators who feel the same pressure you probably feel right now.

Today we close out the series with part 3: meaning. 

Summary: Treat your career as something you design, not something that just happens to you. Write down what progress actually means for you this year. Set one clear rule that helps you decide when a role still deserves your energy and when it is time to start writing a new chapter. You’ll ship a lot of stuff in your life. You only get one self, one mind, one body, and a short list of things that genuinely light you up. Building a career that does not hollow you out starts when you let those things set the terms.

We’ll hear from 19 people and we’ll cover:

• Progress tells you if the work Is working
• Choosing work that deserves your time
• Keeping work from taking over
• Feeding your second self
• Zooming out far enough

Progress tells you if the work is working

A lot of the operators I chatted with don’t talk about happiness like it suddenly arrives. They describe it as something you feel when things actually start to move. Our first guest gets there right away by tying happiness directly to progress, the kind that tells you you’re not stuck.

Rich Waldron: Auditing whether work is actually moving

First up is Rich Waldron, Co-founder and CEO at Tray.ai. He’s also a dad, and a mediocre golfer.

Progress sits at the center of Rich’s definition of career happiness. He treats it as a felt sense rather than a dashboard metric. When work advances in a direction that makes sense to him, his energy steadies. When that movement slows or stalls, frustration surfaces quickly and spreads into everything else. That feeling becomes a cue to examine direction rather than effort.

“Happiness is mostly driven by progress.”

That framing resonates because it names something many operators struggle to articulate. Long hours can feel sustainable when the work moves forward. Light workloads can feel draining when days repeat without traction. Progress gives work narrative weight. It answers a quiet internal question about whether today connects to something that matters tomorrow.

• Rich also points to patterns that erode meaning over time.
• Roles with little challenge dull attention, even when the pay is generous.
• Constant activity without visible change breeds irritation that lingers after work ends.

Both conditions interrupt momentum. The mind keeps searching for movement that never arrives. Rest stops working because unresolved motion occupies every quiet moment.

Progress also shapes identity beyond work. When things move in the right direction, attention releases its grip on unfinished problems. Rich links that release to showing up better at home. He describes being more present as a parent because mental energy is no longer trapped in work that feels stuck. Forward motion restores proportion. Work keeps its place as one part of a full life rather than the dominant one.

Balance emerges as a byproduct of this orientation. You choose problems that move. You notice when progress fades. You adjust before frustration hardens into burnout. That rhythm preserves meaning over long career arcs and keeps work aligned with the person you want to remain.

Key takeaway: Track progress as a signal of meaning. When your work moves in a direction you respect, it stays contained, your identity stays intact, and the rest of your life receives the attention it deserves.

Samia Syed: Tracking personal growth

That’s Samia Syed, Director of Growth Marketing at Dropbox.  She’s also a mother, outdoor fanatic, and an avid hiker.

Progress became the scorecard Samia relies on to keep her career from consuming her sense of self. Early professional years trained her to chase perfection, because perfection looked measurable, respectable, and safe. That mindset quietly tightened the frame around what counted as a good day. Effort increased, expectations rose with it, and satisfaction stayed elusive because the standard never settled.

Progress creates a different rhythm. It shows up in motion you can recognize without squinting. Samia pays attention to signals that accumulate instead of reset:

• Teams moving forward together rather than cycling through urgency.
• People developing judgment and confidence over time.
• Personal growth that feels lived-in rather than optimized.
• A child learning, changing, and surprising you in ways no metric could predict.

That framing matters because it ties work back to a broader life rather than isolating it. Progress carries meaning when it connects professional effort to personal identity. Samia talks about watching her daughter grow with the same care she gives to her team’s evolution. Growth becomes something you witness and participate in, rather than something you chase or defend. That mindset keeps work from becoming the only place where worth gets measured.

“Anchoring on perfection as your metric for happiness sets you up for unhappiness. Progress is where I find it now.”

Many careers quietly reward polish over development and composure over learning. Progress resists that pressure by valuing direction and continuity. It leaves room for ambition while protecting a sense of self that exists beyond job titles. You still push forward, but you also recognize that your life holds meaning across roles, seasons, and relationships that no performance system can fully capture.

Key takeaway: Track progress instead of perfection. Pay attention to growth across work and life, because meaning comes from seeing yourself develop over time, not from chasing a standard that keeps moving.

Jonathan Kazarian: Tracking growth across life health and work

That’s Jonathan Kazarian, Founder & CEO of Accelevents. He’s also father and a frequent sailor.

Jonathan keeps work from consuming his identity by actively measuring progress in more than one place at the same time. He pays attention to movement in business, health, and personal life, and he revisits those signals regularly. That habit creates distance between who he is and what he works on. Work becomes one lane of progress instead of the entire road.

Growth carries real weight in his thinking because it shows up as momentum you can feel. He talks about forward movement as something tangible, the sense that effort today pushes life somewhere better tomorrow. Setbacks still happen, but they do not erase the broader trajectory. He treats progress as something he can influence through consistency and patience, rather than something granted by promotions or external validation.

That perspective shows up clearly in how he describes building over time. He stayed with a product that began as a narrow point solution and helped push it forward for more than a decade. The category evolved, the scope expanded, and the work matured alongside him. Long arcs like that reinforce identity instead of flattening it. You grow with the work, and the work grows without defining your entire sense of self.

“As long as I’m continuing to feel like I’m progressing in life, in business, in health, then that keeps me happy.”

Parenthood sharpens this system rather than disrupting it. Responsibilities shift, time compresses, and priorities gain texture. Progress starts to show up in quieter ways, including energy levels, presence at home, and the ability to stay engaged without burning down the rest of life. Tracking growth across these dimensions keeps work important without letting it dominate the scoreboard.

Careers hollow out when progress collapses into a single metric. Jonathan avoids that trap by widening the frame and checking it often. That practice preserves meaning because it ties happiness to steady movement across a full life, not to any single role or outcome.

Key takeaway: Track progress across work, health, and personal life at the same time. That habit keeps work in proportion and reinforces a sense of meaning built on long-term growth rather than short-term identity.

Work That Earns Its Place

Kim Hacker: Choosing roles with daily visible impact

That’s Kim Hacker, COO at Arrows. She’s also a puzzle master, plays a lot of beach volleyball and recently started learning archery!

Kim keeps work from consuming her identity by choosing roles where contribution is obvious on a daily basis. She speaks candidly about balance being unresolved and ongoing. The pull toward work comes from enjoyment, energy, and a steady stream of problems worth solving. That dynamic shapes how she evaluates her career far more than calendar rules or wellness checklists.

Her time at Arrows reflects that preference clearly. She works in an early-stage environment, holds multiple responsibilities, and sees decisions turn into outcomes quickly. Problems arrive with sharp edges and clear consequences. Solutions create visible movement inside the business. That cadence builds meaning because effort connects directly to progress rather than disappearing into planning cycles or abstract roadmaps.

“I feel like I am moving the needle every single day.”

That sense of usefulness acts as a stabilizer when balance feels elusive. Kim describes earlier periods of her career where dissatisfaction lingered and uncertainty followed. She questioned whether the tension came from her own expectations or the environment around her. Over time, she noticed that fulfillment tracked closely with two conditions working together:

1. The work created visible change within a short window.
2. The people around her noticed and acknowledged that contribution.

Those signals help prevent work from becoming the sole source of identity. You can enjoy working hard when the value is clear and shared. You can step away when needed because the work already left a mark. Kim encourages people who feel stuck to examine whether their current role provides that clarity. If contribution feels invisible or unrecognized, the issue deserves attention rather than endurance.

Key takeaway: Choose roles where your effort produces visible progress and receives recognition from the people around you. Clear contribution creates meaning at work while leaving room for identity to extend beyond it.

Mac Reddin: Checking work against 3 personal conditions

That’s Mac Reddin, Founder and CEO of Commsor. He’s also a cat dad, home chef and an avid runner.

Mac keeps work from consuming his identity by actively checking whether it still deserves a central place in his life. He uses three personal conditions as a filter for every role, product, and company he commits to. These conditions act as a living boundary between meaningful effort and empty motion.

The first condition centers on demand. He wants to work on something people genuinely want to buy, not something that survives on persuasion, internal hype, or optimistic forecasts. Real demand creates a sense of purpose because the work connects to an actual need. That connection grounds long hours in reality rather than ego. When customers stop showing up, meaning erodes quickly.

The second condition focuses on the people involved. Mac chooses to build alongside people who challenge his thinking and make the day feel lighter rather than heavier. He values shared problem solving, mutual respect, and a sense that the work improves everyone involved. Teams shape identity over time, so he pays attention to whether collaboration feels energizing or draining.

• The product solves a problem customers care about enough to pay for.
• The team includes people worth learning from and spending time with.
• The work still feels engaging during ordinary days.

The third condition tracks enjoyment at a visceral level. Mac pays attention to whether he still wants to talk about the problem for hours without rehearsing interest. He notices whether curiosity shows up naturally or whether motivation requires force. When all three conditions faded during a previous chapter, he recognized the signal and changed direction. That decision preserved his sense of self by separating who he was from what he happened to be building at the time.

“If those three things are true, 99 percent of everything else will figure itself out.”

This habit creates meaning by treating work as a choice that earns its place rather than an obligation that expands unchecked. The conditions keep ambition intact while preventing work from becoming the only source of validation. They create space for other identities to coexist without guilt or explanation.

Key takeaway: Regularly evaluate your work against personal conditions that measure demand, people, and enjoyment. When work continues to earn its place through those signals, it stays meaningful. When it fails them, changing direction protects your identity beyond the job and keeps life larger than work.

Chris Golec: Choosing early stage building work

That’s Chris Golec, Founder & CEO at Channel99, former Founder and CEO of Demandabase. He’s also  a father, an avid outdoors mountain biker, skier, hiker.

Chris keeps work from becoming his entire identity by repeatedly choosing company-building roles that demand creation, judgment, and emotional presence. He stays close to the act of making things because that work keeps his attention anchored in effort rather than reputation. There is always something underway, something fragile enough to need care. That constant act of building gives work a clear boundary, because the satisfaction comes from the process rather than from how it reflects back on him.

He speaks openly about the emotional texture of startup life. The lows arrive as part of the job, and they arrive with force. Long weeks stretch into months, momentum slows, and doubt shows up quietly at the edges of the day. Chris treats those stretches as proof that he chose a path with real stakes. The highs carry more weight because they follow sustained pressure, and the work feels earned rather than granted.

“I love innovation. I love building things. I always have something cooking.”

That line captures the habit underneath his happiness. He returns to building because it keeps his sense of self larger than any single role. When people expressed disbelief that he would leave a comfortable position to start again, the reaction highlighted how often careers drift toward safety by default. Chris made an active choice to stay in environments where curiosity and creation still pull him forward.

There is a practical system embedded in this pattern. He measures meaning by asking whether the work still feels worth doing when conditions turn rough. That way you can stay deeply engaged without letting work define the full shape of your life. The identity stays rooted in choosing the work, not in clinging to outcomes or titles that fade quickly.

Key takeaway: Return to work that rewards sustained building rather than surface-level wins. When the process itself feels absorbing during difficult stretches, work remains one part of a full life instead of becoming the whole thing.

Hope Barrett: Feeding curiosity across multiple domains

That’s Hope Barrett, Sr Director of Product Management, Martech at SoundCloud. She’s also an avid reader and a news junkie.

Hope keeps work from becoming her entire identity by rotating interests inside the same role instead of collapsing everything into one narrow lane. Her days move across performance marketing mechanics, platform behavior, DSP details, and music culture, often within the same afternoon. That rotation matters because attention follows curiosity, and curiosity keeps the work feeling alive. She has experienced jobs where strong compensation and recognizable titles existed alongside daily frustration, and those memories sharpened her sense of what kind of work deserves her energy now.

She describes herself as a generalist, and her manager sometimes uses the word fixer. Both labels point to the same behavior, which involves scanning widely, connecting dots, and stepping into problems that resist tidy definitions. That mindset shows up in how she structures her time and interests rather than how she frames her job title. A typical rhythm includes:

• Tracking how platforms like Google shift behavior and incentives, then translating those shifts into practical decisions.
• Digging into DSP mechanics to understand where efficiency hides and where waste creeps in.
• Staying close to music and culture because context shapes judgment and taste in ways dashboards never capture.

That variety keeps her engaged and prevents work from hardening into a single story about who she is.

At SoundCloud, that kind of curiosity has room to exist without being squeezed into a narrow mandate. The environment supports people who move laterally, ask uncomfortable questions, and carry more than one mental model at a time. That support matters because identity erosion often starts when curiosity becomes a liability instead of an asset. Her work feels sustainable because it mirrors how her mind actually works across domains.

“I enjoy knowing a lot of different things about different areas. I like seeing how it comes together, and I’m able to do that here.”

Meaning shows up in the texture of her days rather than in abstract goals. She talks about staying up too late reading because interest pulled her forward, not because urgency demanded it. The difference feels subtle until you live through both versions of work. One drains energy quietly over time, while the other keeps you alert and invested without demanding total surrender.

Many careers drift toward identity collapse because specialization feels safer than curiosity. Hope’s pattern points in a different direction. She feeds multiple interests inside her role, pays attention to what actually energizes her, and uses that signal as a boundary. That habit keeps work meaningful while leaving room for a life that extends beyond it.

Key takeaway: Preserve meaning by rotating genuine interests inside your role. Pay attention to what holds your curiosity, build space for that variety during the workday, and let that rhythm keep work from becoming the whole story of who you are.

Keeping work from taking over

Simon Lejeune: Treating work like a game

Here’s Simon Lejeune, VP of Growth at Wealthsimple. He’s also a self-described fun uncle.

Work stays contained when Simon actively lowers the perceived stakes of what he does. He builds ambitious products, ships aggressively, and cares about outcomes, but he keeps a mental habit that prevents the work from swallowing his identity. He reminds himself, repeatedly and without ceremony, what the job actually represents in the grand scheme of things. That reminder shows up during long days, tense meetings, and moments when momentum starts to feel personal.

He uses humor and scale as tools, not as coping mechanisms. Simon talks about being a tiny speck floating in space, and that image matters because it shrinks the emotional footprint of the work. He gives himself permission to enjoy the process without turning every decision into a referendum on self-worth. He treats fun as a requirement of the job rather than a reward earned after burnout. That framing changes how eight or ten hours a day feel in your body.

“Sometimes I just remind myself, I’m selling bank accounts. I’m not saving lives. It’s fine.”

That sentence resets the room. It keeps urgency from turning into self-importance. It keeps mistakes from feeling catastrophic. It also creates a working environment where people stay lighter on their feet and easier on each other, because nobody is pretending the stakes are existential.

Simon reinforces this boundary by treating work as a structured game. Games have constraints, feedback, and visible progress. They reward curiosity. They punish fixation. He describes watching dashboards refresh with genuine excitement, because each result feels like a turn rather than a verdict. That mindset keeps momentum enjoyable instead of draining. It also makes losses tolerable, because the next move always exists.

This habit protects meaning by preserving space for a second self. Simon does not outsource fulfillment to titles, launches, or quarterly goals. He chooses a way of working that stays engaging without demanding total allegiance. That decision keeps work in its lane and leaves room for a life that does not collapse when the job changes.

Key takeaway: Regularly restate what your job represents and what it does not represent. Shrinking the perceived stakes keeps ambition intact while protecting identity. That habit makes it easier to enjoy the work without letting it become the whole story of your life.

Ana Mourão: A mental buffer between noticing and doing

That’s Ana Mourão, CRM, Customer Data and CDP Advisor. She’s also a mother, home baker, amateur photographer and cat mom.

Ana keeps work from taking over by deciding when an idea earns the right to become action. Evenings and weekends hold their own weight. They include family time, baking sessions, and the familiar presence of a cat moving through the house. Those moments carry texture and comfort. They reinforce a sense of self that exists before calendars and priorities enter the room.

Curiosity still stays active during that time, and it stays active on purpose. Ana reads the newspaper. She scrolls LinkedIn. She notices patterns that echo conversations happening at work. The habit sits in observation rather than execution. She treats ideas as something to hold, not something that demands immediate response. That posture matters inside large companies where speed often masquerades as value and everything arrives with urgency attached.

“Even if I’m relaxing, like reading the newspaper or browsing LinkedIn, I may read something and think, oh, that connects to that conversation or issue we were discussing.”

She keeps a mental buffer between noticing and doing. Ideas get parked for later discussions instead of turning into tasks that bleed into personal time. That buffer gives her room to stay present while still feeding the part of her brain that enjoys connecting dots. Many people struggle here because awareness quietly turns into obligation. Ana keeps those two states separate through practice.

The habit becomes practical in ways that feel familiar:

• Reading without forwarding links or opening work threads.
• Scrolling without drafting replies in your head.
• Letting patterns surface without scheduling follow-up work.

Ana describes this rhythm as going on and off often enough to stay energized. Attention becomes something she lends intentionally. Over time, that choice preserves a fuller identity and keeps curiosity alive instead of drained.

Key takeaway: Meaning holds when your career stays in proportion. Build a habit of noticing ideas without immediately acting on them, so work remains one chapter in a life that has many others.

Tiankai Feng: Anticipation planning

That’s Tiankai Feng, Data & AI Strategy Director at Thoughtworks and Author of Humanizing Data Strategy. He’s also a musician, rapper, an avid sci-fi book enthusiast, and a silly dad of 2.

Career satisfaction erodes quickly when frustration attaches itself to identity. Tiankai grounds his thinking in control, which keeps that erosion from setting in. He pays close attention to what sits within his influence and what does not. When something can be changed, he acts on it directly. When it cannot, he lets it move past without carrying it forward. That habit prevents bad days from turning into personal narratives, which is where many long careers quietly lose meaning.

That discipline shapes how he processes negativity. He treats negativity as a behavioral pattern rather than a personality trait. Patterns can be rewritten through repetition. His default mode becomes solution oriented because attention stays focused on movement rather than rumination. That choice stands in sharp contrast to workplaces that reward visible stress as a proxy for importance. Emotional containment becomes a form of self respect rather than disengagement.

The most practical part of his system shows up in a small, repeatable morning ritual. He starts each day by scanning his calendar for something he genuinely anticipates. Sometimes it involves work. Sometimes it does not. The effect remains consistent. The day acquires emotional gravity before the first task begins.

“Every day in the morning, I look at my calendar and see what I am looking forward to.”

Anticipation creates lift. Meetings feel lighter. Interruptions feel smaller. Pressure softens because attention already points forward.

He extends that habit beyond the workday and into longer time horizons. Vacations, family milestones, and personal plans sit visibly on the calendar. Those future anchors reduce the emotional weight of present noise. Work occupies a defined portion of life rather than spreading across all of it. Meaning stays intact because identity draws from more than performance or outcomes.

The structure becomes easy to apply when broken into concrete behaviors:

• Scan your calendar daily for one moment you genuinely anticipate.
• Place personal events on the calendar with the same care as work commitments.
• Keep at least one meaningful future moment visible beyond the current week.

These behaviors keep the second self active and nourished. Work remains important, but it no longer monopolizes emotional bandwidth.

Key takeaway: Build a daily anticipation habit that extends beyond work. Each morning, identify one upcoming work moment and one personal moment that you genuinely look forward to, then protect both on your calendar. That practice keeps work contained, preserves identity, and reinforces a life structure where meaning comes from multiple directions rather than a single role.

István Mészáros: Choosing who you are when work ends

That’s István Mészáros, Founder and CEO of Mitzu.io. He’s also a busy dad. 

Istvan keeps work from consuming his identity by making a clear decision about how his evenings end. He finishes the workday and sits on the floor with his child, building Lego sets piece by piece. That habit anchors his attention in something tactile and human. The sound of plastic bricks clicking together replaces notifications, dashboards, and open loops from the day.

That practice carries more weight because his work life demands constant judgment. Founding a company introduces a steady stream of decisions that follow you home, linger during dinner, and show up again at night. Over time, Istvan develops a sharper filter for what deserves emotional energy. He moves faster on decisions that matter and releases the rest without ceremony. Playing with his child reinforces that filter because the contrast between urgency at work and presence at home becomes impossible to ignore.

“I just do not care anymore about significant decisions in life that are not worth my energy.”

That mindset changes how pressure lands. Customer wins still bring excitement, especially when a small team earns trust from companies many times its size. Ambition remains intact, and bold asks feel energizing rather than draining. The difference is that work no longer defines the outer edge of his life. The hours spent building towers on the floor create a separate identity that stays whole even when work intensity spikes.

You can see the behavior repeat in small, concrete ways. He decides faster on purchases. He accepts imperfect choices without spiraling. He protects time that has no productivity upside. Those choices form a pattern that keeps work contained within its proper boundaries:

• He ends the day with an activity that requires full presence.
• He resists carrying unresolved work decisions into family time.
• He treats attention as a finite resource rather than an infinite one.

Meaning comes from repeated actions that remind you who you are outside of work. Istvan builds that reminder every evening by choosing play over optimization and presence over performance.

Side note: Istvan’s answer could reasonably live in any part of this series, including stability or connection, because it operates as a habit and boundary system. The behavior protects mental energy by shutting down rumination, it happens in the context of family, and it creates a daily role change that limits how far work is allowed to travel. It ultimately fits best here because the habit defines who he chooses to be when the workday ends. Sitting on the floor building Lego draws a clear line around work’s importance and keeps it from becoming the sole source of identity.

Key takeaway: End each workday with a physical, absorbing activity that belongs to another part of your life. Repeated presence in that role keeps work from becoming your primary identity and preserves meaning when pressure rises.

Feeding your second self

Danielle Balestra: Feeding interests unrelated to work

Here’s Danielle Balestra, Fractional Marketing Technologist, former Director of Marketing Technology and Operations at Goodwin. She’s also a big soccer fan, a NY Mets fanatic, movie buff and an avid reader.

Danielle treats growth as an ongoing practice that coexists with the rest of her life. She keeps learning through conferences, books, and webinars, and she checks whether that learning still feels energizing rather than performative. Many people in martech confuse momentum with meaning and mistake constant motion for progress. Danielle stays grounded by caring about steady development and pride in delivery, and she resists the pressure to turn every season into a résumé upgrade.

She protects meaning by investing attention in experiences that exist outside professional output. Movies matter to her because they offer a complete sensory experience that slows time and invites shared focus. The ritual carries as much weight as the film itself.

• Sitting together in a theater.
• Sharing food.
• Absorbing sound, visuals, and story.
• Talking about what resonated afterward.

Those moments create memory and perspective, and they remind you that attention can feel generous rather than transactional.

“I really love movies. I think it’s amazing how they put these things together, how they tell a story visually, with sound, as a full experience.”

Her curiosity extends into other human stories as well. She finds meaning in cheering for women’s soccer and following teams like the New York Mets with hopeful loyalty. Sports fandom becomes a lesson in patience, belief, and shared disappointment, and it reinforces that enthusiasm does not need a return on investment. That kind of attachment stretches identity in healthy directions.

Danielle also sets clear expectations for herself as a professional. She focuses on doing good work, learning from it, and continuing to grow over time. She leaves space for joy, storytelling, and shared experiences with her kids because those parts keep her grounded as a person. Meaning stays intact when work holds its place among other sources of fulfillment instead of crowding them out.

Key takeaway: A durable career grows alongside interests that exist beyond work. Feed parts of yourself that never show up in performance reviews, because meaning depends on remembering that a job supports a life rather than defines it.

Jeff Lee: Continuing to build personal projects after the workday ends

That’s Jeff Lee, Lifecycle Marketing Technical Lead at Calm. He’s also a dad, golfer, home chef, light programmer.

Jeff keeps work from becoming his entire identity by continuing to build things that belong only to him. He describes himself as a tinkerer, someone who feels most grounded when he is creating, testing, and iterating. That habit shapes his career choices, but it also lives outside his job. The separation matters because it preserves a sense of self that exists without titles, promotions, or external approval.

The work he gravitates toward tends to sit at the intersection of marketing and engineering. Speed, feedback loops, and hands-on problem solving keep him engaged long enough to lose track of time. He talks about entering flow during the day and suddenly realizing the afternoon is gone. He also talks about reopening his laptop at night, after his kids are asleep, because the activity itself feels satisfying. The motivation comes from curiosity and enjoyment rather than pressure or expectation.

“I like to do things. I like to build things. I tend to work on the things that interest me, or the things I get into a flow state with.”

Jeff is direct about the implications of this choice. He acknowledges that following interest does not map cleanly to senior leadership tracks. The industry often praises passion in public while rewarding predictability and patience behind closed doors. Jeff chooses a path shaped by engagement and personal interest, and he accepts the constraints that come with that direction. The clarity shows up in how he talks about work as something he enjoys rather than something he performs.

The system becomes clearer when he describes what happens outside formal work hours. The tinkering continues because it belongs to him. It includes experimenting, building for fun, and chasing ideas with no requirement to justify the outcome. That practice keeps meaning intact. The work remains one expression of his identity instead of the container that holds all of it.

Key takeaway: Maintain a habit of building something for yourself that has no career outcome attached to it. Personal projects preserve identity, protect meaning, and keep work from becoming the only place where fulfillment lives.

John Saunders: Keeping a builder practice outside of work

That’s John Saunders, VP of Product at Power Digital Marketing. He’s also a dad, dog dad of two, big golfer, big beach guy.

John keeps work from expanding into his entire identity by maintaining a constant builder loop that exists outside formal responsibilities. He experiments because experimentation keeps him oriented and awake. That habit gives his days a sense of forward motion without attaching meaning to a single role or outcome. Building stays present whether he is at work or far away from it.

He describes himself as a builder at heart, and that description carries weight because it shows up in behavior rather than ambition. He tests tools, ideas, and workflows with curiosity rather than expectation. Some experiments feed directly into his job, and others remain personal and unfinished by design. That separation matters because it keeps his sense of progress distributed across life instead of concentrated in one place.

His builder loop stays grounded through ordinary, physical anchors. Golf creates space and rhythm. Time with his wife and dogs brings texture and routine. Those moments pull attention back into the body and out of abstract thinking. They reinforce the idea that creation belongs in many parts of life, not just in professional output.

John talks about this plainly, without dressing it up as a framework or philosophy.

“As long as I’m building, experimenting, and moving forward, that’s really what keeps me happy.”

This mindset quietly challenges how innovation gets treated across the industry. Innovation often turns into performance, then into process, then into pressure. John treats it as a personal practice that stays flexible and human. He builds because building feels right, and that choice keeps work meaningful without letting it define the full shape of his life.

Key takeaway: Maintain a personal habit that produces momentum beyond your job. Feed a builder instinct through experimentation in multiple areas of life so meaning stays anchored to who you are, not only to what you do at work.

Ashley Faus: Group creative rituals outside of work

That’s Ashley Faus, Head of Lifecycle Marketing at Atlassian and the author of Human-Centered Marketing: How to Connect with Audiences in the Age of AI. She’s also an avid baker, a fitness fiend, actor and singer.

Ashley actively protects her identity by committing to creative and physical activities that require other people and fixed time blocks. She pursues goals at work and in the gym, but she gives equal structural weight to rehearsals, cast gatherings, and baking sessions meant for others. These commitments exist on the calendar before work expands into the evening. The structure forces regular exits from professional mode and creates space where progress has nothing to do with a title or output.

Her creative life follows a clear pattern that repeats across different settings. Each activity must involve contribution and presence with other people. The behavior shows up in a few consistent ways:

• Musical theater rehearsals that depend on harmony and timing with others.
• Baking projects planned around sharing food at work or rehearsal.
• Gym sessions chosen for the energy of collective effort rather than convenience.

The pattern keeps effort social and visible, which prevents work from becoming the only place where discipline and growth exist.

“I do musical theater with other people because singing live with other people is cool. I cannot harmonize with myself.”

That mindset carries into how she thinks about physical training. She chooses gyms filled with people training for specific goals and public milestones. She notices who is preparing for a marathon or chasing a personal record. She draws motivation from seeing that effort up close and from knowing her own consistency becomes part of that environment. The room itself becomes a reminder that progress belongs to many parts of life, not a single career track.

Ashley manages balance across longer arcs instead of daily symmetry. She plans in six to twelve month windows and checks whether creative, physical, and professional commitments all include shared experiences. She makes trade-offs without guilt and adjusts the mix as seasons change. The structure keeps work from quietly expanding because other roles already claim time and attention.

This system works because it treats identity as something practiced through participation. Work remains meaningful, but it never becomes the sole container for ambition or fulfillment. Shared creative commitments anchor her sense of self across roles, environments, and phases of life.

Key takeaway: Schedule recurring creative and physical commitments that require other people and protect them with the same seriousness as work. Shared participation keeps identity broader than any single role and preserves meaning across career changes.

Anna Aubucho: Maintaining a second self through solo creative practice

That’s Anna Aubuchon, VP of Operations at Civic Technologies. She’s also a full time mom, part time vibe coder – avid wheel thrower.

Solo creative practice acts as a counterweight to work that constantly demands cognition, judgment, and progress. Anna keeps that counterweight intact by committing time to activities that are quiet, individual, and deliberately disconnected from professional achievement. She enjoys work and thrives on learning, but she also recognizes how mentally taxing it becomes when every challenge lives in the same cognitive lane. A solo outlet introduces a different kind of effort, one that restores rather than extracts.

That practice takes shape through wheel throwing, where attention narrows and expectations flatten. The value comes from being alone with a physical process that resists control. Clay reacts to pressure immediately. Forms collapse without warning. Progress shows up through repetition rather than cleverness. You fail early and often, and you continue anyway. That rhythm trains patience and emotional steadiness in a way work rarely does.

“It’s just me, the wheel, my clay, and what I want to create that day.”

The learning loop matters more than the object. Failure arrives without commentary and leaves without consequence. There is no narrative to manage and no outcome to justify. That experience builds resilience because it normalizes starting over. Over time, that muscle carries into professional life. Iteration feels calmer. Mistakes feel bounded. Momentum comes from action rather than self-evaluation.

The deeper system at work is identity diversification. Anna feeds a part of herself that does not care about titles, velocity, or external feedback. You can see the structure clearly:

• A solo practice with no audience.
• Physical feedback instead of abstract judgment.
• Failure that resolves through repetition.
• Growth that happens quietly and predictably.

Careers hollow people out when they become the only place where growth and challenge exist. Meaning stays intact when at least one part of life follows a different set of rules.

Key takeaway: Protect a solo creative practice that develops a second identity outside work. Choose something physical and iterative, and return to it often so your sense of self stays larger than your role.

Zooming out far enough

Ruari Baker: Preserving identity through regular travel

That’s Ruari Baker, Co-Founder and CEO of Allegrow. He’s also an avid traveler, chess master in training, pickle ball fanatic.

Regular travel plays a concrete role in how Ruari keeps work from overtaking his sense of self. He schedules trips with the same intention other people reserve for quarterly planning, and those trips exist entirely outside his professional identity. New places force attention outward. Food tastes unfamiliar. Streets follow different rhythms. Days stretch or compress in ways that make calendars feel optional. Those experiences create distance from job titles and performance metrics, and that distance keeps identity from collapsing inward.

Ruari talks about travel in practical, sensory terms rather than lofty ideas. He notices flavors, pacing, and how people structure daily life. Those details matter because they reinforce a broader view of what a life can hold. Exposure to other cultures recalibrates ambition and reminds him that meaning shows up in many forms. The result is a mental posture that treats work as one element among many rather than the organizing principle of everything else.

“Being able to see a new culture, a new part of the world fairly regularly keeps my spirits pretty high. I love new flavors, cuisine, and seeing different parts of the world.”

That boundary carries into how he structures his workday. Ruari deliberately concentrates context switching into the morning, then reserves afternoons for a single problem that deserves sustained attention. Email and meetings lose their power to dictate direction. Deep work becomes a chosen activity rather than a stolen moment. That structure gives his work coherence and preserves mental space for thinking that feels purposeful.

Several conditions make this possible, and they are not accidental. He works with a team he trusts. Responsibility spreads across capable people. Ownership does not bottleneck at the top. Those elements combine to support a rhythm that values depth over constant responsiveness. Many teams talk about focus while rewarding interruption. His setup rewards judgment and follow through instead.

Travel and focused work reinforce each other. Travel expands identity beyond the job. Focused work restores a sense of craft inside it. Together they form a system that keeps career ambition in proportion to the rest of life, without turning either one into a performance.

Key takeaway: Schedule experiences that sit completely outside your professional identity, and structure work in a way that prioritizes depth over noise. Those choices protect meaning by keeping work important without allowing it to become the entire story.

Guta Tolmasquim: Building a personal product roadmap

That’s Guta Tolmasquim, CEO at Purple Metrics. She’s also an avid urban life traveler and big time sports and book worm.

Guta treats happiness as something she deliberately constructs and revisits, using the same rigor she applies to product thinking. When asked how she stays happy while carrying a demanding career, she describes a system built from repeated observation rather than aspiration. She pays close attention to what restores her sense of self, then she makes room for those elements before work fills the calendar by default.

She starts by naming the inputs that consistently anchor her identity outside of work. These inputs come from memory, geography, and habit rather than productivity advice. Growing up in Rio shaped her need to be near water. Physical movement keeps her grounded. Reading keeps her curious without turning curiosity into performance. Time with friends keeps conversation human rather than transactional. She schedules these inputs because unscheduled priorities tend to disappear.

Those inputs show up in her routine as concrete commitments.

• Sports appear in her week because her body needs exertion.
• Water and the ocean reappear because they reconnect her to where she came from.
• Books stay close because curiosity deserves space without deadlines.
• Friends stay present because work relationships alone narrow perspective.
• Travel and city movement interrupt routines that dull attention over time.

“I understand the function of the stuff that makes me happy and try to add it to the system.”

She also watches closely for signals that something has slipped. Stress, fatigue, and irritability serve as feedback rather than character judgments. She treats those moments like a bug report and traces them back to missing inputs. Sleep quality, movement gaps, and neglected friendships usually explain the issue. She adjusts the system instead of demanding more endurance from herself.

“When something’s wrong, I try to understand the signals. Those are metrics on unhappiness.”

Her planning horizon stays intentionally short. Long-range life plans increase anxiety for her, so she limits them. She keeps a modest list of books she wants to read and ideas she wants to explore, then she returns attention to the present week. That constraint protects her from turning life into a deferred reward structure where meaning waits on future milestones.

The broader lesson feels uncomfortable because it challenges how many careers reward overextension. Work expands naturally when nothing else has equal structural weight. Guta counters that gravity by treating non-work identity as something that requires regular scheduling, attention, and repair.

Key takeaway: Keep work from absorbing your identity by explicitly scheduling the inputs that define you outside of it. Track stress as feedback, restore what is missing, and keep your planning horizon short enough that meaning stays rooted in daily life rather than postponed to the future.

Pam Boiros: Feeding identities that have nothing to do with work

That’s Pam Boiros, Fractional CMO and Marketing advisor, co-founder Women Applying AI. She’s also a proud Bostonian and a yoga lover, an avid reader and an ancestral detective.

Pam keeps work from consuming her identity by consistently investing in pursuits that have no professional payoff. She spends time on activities that sit completely outside career momentum, including yoga, reading, and deep personal research. These interests exist on their own terms. They introduce scale and patience into her life, which naturally limits how much authority work gets to claim.

Career culture rewards total absorption and constant relevance. It quietly teaches people to answer the question “Who are you?” with a job title. Pam disrupts that pattern by returning to practices that do not care about optimization or visibility. Genealogy becomes powerful in this context because it stretches identity across centuries rather than quarters. It forces attention away from personal advancement and toward continuity.

“As I dug into my own genealogy, I found the women in my family tree are some of the most interesting characters.”

Those stories carry weight because they come from lives shaped by permanence and consequence. Some women in her family crossed oceans knowing they would never return home. Distance meant separation without resolution. Their labor held families together and shaped communities, even when history failed to preserve their names. Sitting with those realities reshapes how contribution feels in the present.

This habit changes how success lands day to day. Career metrics lose their emotional leverage when placed next to lives measured by endurance, survival, and care. Pam reinforces that perspective through repeatable behaviors:

• Reading historical records filled with gaps and unfinished narratives.
• Practicing yoga to reconnect with physical presence after long stretches of cognitive work.
• Studying lineage to anchor identity beyond professional output.

That system keeps work in proportion. Ambition still exists, but it shares space with memory, curiosity, and lineage. Identity stretches wider than any single role, title, or season of output.

Key takeaway: Meaning stays intact when identity extends beyond work. Regular investment in long horizon pursuits creates perspective, limits career overreach, and preserves a sense of self that outlives professional cycles.

Outro

This is by far my favorite question to ask in every interview. There’s a lot of similarities and threads but everyone has a unique take on how happiness shows up when life feels like it is moving somewhere you actually care about. Almost everyone talked about visible progress, even in tiny pieces. A product inching forward. A kid learning a new word. A company refusing to stall out. A new skill that used to feel impossible and now feels like play.

You hear it in the builders who chase interesting problems until the clock disappears. In founders who use simple rules to decide when it is time to pivot or walk away. In operators who keep learning on purpose, through books, movies, conferences, and weird side quests that have nothing to do with quarterly OKRs but somehow keep their brain awake.

You also hear how often that meaning lives outside the job description. 

• Guta reverse engineers her own happiness like a product roadmap, checking for missing “features” when stress spikes. 
• Ashley finds it in harmonies, buttercream, and heavy lifts surrounded by other people chasing their own goals. 
• Pam looks backward through family history and draws strength from women whose names never made it into the company org chart. 
• Anna sits at the wheel, wrecks a bowl, and turns it into a lesson in resilience that quietly feeds her leadership style.

If you take one thing from this episode, let it be this. Treat your career as something you design, not something that just happens to you. Write down what progress actually means for you this year. Protect one creative outlet that belongs to you and not to your employer. Set one clear rule that helps you decide when a role still deserves your energy and when it is time to start writing a new chapter.

You will ship a lot of campaigns and tools in your life. You only get one self, one mind, one body, and a short list of things that genuinely light you up. Building a career that does not hollow you out starts when you let those things set the terms.

I hope you’ve enjoyed getting a bit of wisdom from all 50 of these operators. Now go have fun out there but remember to build the daily systems, protect the people, and choose the work that lets you stay fully human while you do it.

Listen to the full episode ⬇️ or Back to the top ⬆️

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Intro music by Wowa via Unminus
Cover art created with Midjourney (check out how)

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