Reading through Brene Brown’s Dare To Lead, a modern classic on leadership, I kept coming back to a simple phrase in the first chapter. “Clear is kind.”
I’m somewhat of a reformed people-pleaser, and I can trace my people-pleasing tendencies back to my desire to fit in and have people like me (big surprise there). But when I step back and look at my life’s trajectory as objectively as I can, I find the times I've felt the most appreciated and valued weren’t when I mindlessly went along with the crowd or told people what I thought they wanted to hear, but rather when I was brave enough to be clear, open, and honest.
As a leader, it does no good to have unspoken expectations of your team. It’s unlikely people will hit a target they can't see.
My gut feeling is this is why so many bosses feel bad after they fire someone. Sure, there’s a certain amount of empathy for someone who’s lost their job, but there’s also a fair amount of guilt in knowing you didn’t give that person the best chance of success.
We shouldn’t do people’s work for them, but we are responsible for setting expectations and pointing them in the right direction.
Clear is kind.
It’s a mistake to think that your product and your promise are one and the same. That’s too narrow of a view.
I love our coffee, and I hope other people love our coffee, but I’m not under the illusion that people come to us for coffee. Within a stone's throw of our busiest cafe, there are four other options for specialty coffee. People can make coffee at home for a fraction of the price it costs them to come to Cat & Cloud.
Our guests don’t have a barrier between them and delicious coffee. That’s not the problem we’re solving.
As a business, having an amazing “product” isn’t exceptional, it’s simply a prerequisite for getting into the game. I’m using product in quotations because, at the end of the day, the real product is the experience we create. Amazing coffee is a necessary component of that experience, but it alone can’t carry the whole experience.
So if you think you’re in the coffee business, you might be right, but if that’s the only business you’re in, you might be in trouble.
Herman, one of our Team Leaders who happens to have culinary training, has been putting in time in the kitchen.
When Herman works in the kitchen, he wears a chef’s hat.
The first time I saw him wearing it, I knew exactly what he was doing. When I was a production barista, I always brought my own tools with me: tamper, towels, brushes, etc. Sure the shops had tools on hand, but I didn’t see myself as just a coffee shop employee, I was a Barista.
Putting on the hat or bringing in your own tools sends a signal.
A signal to yourself: I’m a professional, I’m proud of my work, and I’m here to get down.
A signal to your team: We’re doing something special here. (plus all the above)
A signal to your guests: We care. You’re going to be well taken care of. (plus all the above)
These signals can come to define your culture. “We’re the kind of coffee shop where all our baristas bring in their own tampers.” or “Most coffee shop kitchen staff don’t see themselves as chefs, but ours do.”
What signals are you sending?
It’s easy to get lost in one or the other. I go through phases where I’m addicted to dreaming—I create multiple worlds in my head or rant about how things could be better, all while lying in my bed or lazily complaining to my friends. On the flip side, I go through phases where I’m so lost in my work that I forget why I’m doing it. Work simply leads to more work and nothing meaningful changes.
We see specialized dreaming and doing roles in business. A CEO vs. a COO for example. But regardless of where we land on an org chart, we all have both dreaming and doing responsibilities for ourselves.
While we might feel more comfortable with one role over the other, my gut feeling is we all have a Dreamer and a Doer inside of us. Much like a business, we're at our best when we have a vision and a plan for moving toward that vision. We might have a community of friends or mentors, but the responsibility begins and ends with us.
Adopting a label of either a Dreamer or a Doer is a cop-out. Dreaming and doing are actions, not permanent states of being. We can choose to exercise both, or we can choose to make excuses for why our ideas never come to life or why we find ourselves stuck despite working so hard.
Often what keeps us stuck isn’t a lack of skills, information, or motivation, but surrendering to the limiting beliefs we have about ourselves.
Opportunity cost is easy to see in terms of material things. “I just bought a new car so I can’t afford to update my entire wardrobe.” But just like material things, beliefs and behaviors have opportunity costs.
What’s the opportunity cost of not believing in yourself?
What’s the opportunity cost of not taking responsibility?
What’s the opportunity cost of not developing and sharing your gifts?
These are the hard questions. This is the hard work.
Every day I wake up in the same room, sit in the same chair, and type on the same keyboard. I drive to the same building, order the same thing (espresso please), and connect with the same people.
Work moves at a glacial pace. In pursuit of the same vision day after day with projects that easily span quarters and sometimes years. To quote Austin Kleon in Keep Going: “Every day is groundhog day.”
When we’re in this perpetual loop, it’s easy to forget that what we’re doing matters or that our work has any impact at all. We falsely believe that because something feels boring or mundane to us, it must feel that way for everyone else.
Here’s a not-uncommon story: Someone discovers Cat & Cloud through our podcast, YouTube channel, or this blog, and decides to make us a part of their vacation to the West Coast—driving two hours out of their way from San Francisco or six hours from Los Angeles. This happens with surprising frequency.
The only reason for people to go so far out of their way is to have an experience. If they just need coffee, they can get that without driving for hours.
So what might feel like groundhog day for everyone behind the counter is something new and magical for someone else. When the road-trippers arrive, we have the opportunity to either make or break our promise. We can choose to live up to our mission of “Inspiring connection by creating memorable experiences” or not.
I’m sure you can see the problem here. Core regulars aside, we don’t know if someone drove across town or trekked 6 hours to get here.
So the obvious thing to do, the most impactful thing to do, the most fun thing to do is to imagine each and every guest has made a special journey to come see us. This also turns out to be true. Because even the people in our neighborhood have 5 other options for coffee a stone's throw away. Even the people who have been to Cat & Cloud hundreds of times still value the experience we create.
As stressful as owning a business can be at times, the adventure of driving to the same building, ordering the same thing, and connecting with the same people isn’t lost on me. I would miss it greatly if it were gone.
The story of your life is the story of what you do day in and day out. Just because you do something every day, doesn’t mean it isn’t completely magical.
Each season of life rolls out challenges for which we are unprepared but also capable of taking on.
It can be tempting to surrender to the overwhelm and drown in guilt or shame or the feeling of not being enough.
But the journey is long and there’s no need to beat ourselves up about where we are while we’re on the way to where we’re going to be.
Shopping for car parts online I added something to my cart, then, second-guessing myself, I used the contact form to ask a question about the part.
A week later I’ve gotten no response to my question but no less than three abandoned cart emails prompting me to finish my purchase.
So while I’ve had a handful of touchpoints with the vendor, none of them were useful for either of us.
I didn’t need a reminder that I left something in my cart, I needed my question answered. Service would have been the quickest path to a sale. I was ready to make a purchase, I just needed a tiny slice of attention.
But the system in place wasn't designed to connect, bring joy, or be of service, it was designed to capture.
It made me think about the allure of new and the devil on our shoulder, whispering in our ear: "Who cares about serving your current customers, how do you capture new ones?" (or personally "Who cares about your current friends, how can you get new ones?")
New is exciting, but the path to a worthwhile new is rarely ignoring the foundation we’ve built and starting from scratch each round.
When I only chase the dragon of new and exciting, I lose, and the people that have put their trust in me lose.
Conversely, the more I water the grass that’s right in front of me in both my business and personal life, the more I simultaneously deepen existing relationships and discover new opportunities.
The paradox of new: the most effective path to new is to put extreme intention and effort into what we already have.
As friends, artists, and business owners, we get to choose what we create—a veritable string of generic abandoned cart emails designed for nobody in particular, or experiences that bring joy and connection to people who truly appreciate and benefit from our work.
Paying attention to the people who are eager to engage with what we're creating is much more useful than trying to capture everyone's attention.
We have more than enough generic art. And by art, I don’t just mean pictures: generic service experiences, generic food, generic branding, and generic marketing campaigns telling generic stories.
I have a bad habit of trying to get so far away from generic that what I create is uncategorizable. While uncategorizable is fine for a hobby, it’s problematic for a business. How can people connect with what we do if they have no way to categorize it?
One of the things Seth Godin talks about that has shaped my perspective on how people can connect with our work is this idea of “genre, not generic.”
Genre as in rhyming with something people are familiar with, or knowing the established norms of an industry or culture. This reminds me of my love for focusing on the fundamentals. In the barista world, tamping level isn’t generic, it’s just what professionals do. Are you familiar with Track Changes in Word? If you’re an editor you are.
So the challenge is to create something that people can sink their teeth into without making it so generic that it simply blends in with everything else.
The formula might be something like this: Mastery of the Fundamentals + Your Quirkiness = Art I’d like to engage with. (A book I’d like to read, a film I’d like to watch, a coffee shop I’d like to visit, a picture I’d like to hang on my wall, etc.)
We’re waiting for you.
Whenever I take time off work, my vacation only starts once I shake the feeling that my absence will somehow create an alternate universe where things spiral in a direction I feel completely uncomfortable with, then when my vacation is over I’ll come back to a workplace that only vaguely resembles the one I left.
But every time I return from a break, things are always more similar than they are different. This isn’t because it’s impossible for change to happen without me, but rather that creating change is difficult. Change is lumbering—even with huge changes in policies and procedures, change in behavior is slow to catch up.
So if you're taking time off work, give yourself permission to fully disconnect. The universe you return to won't be much different than the one you left.
Right now, at this moment, the job you have is the best one you can get.
If you think the job you have isn’t the best one you can get, by all means, go get that other job!
But if this is where you’re going to be, for now, choosing to take it as seriously as you would your dream job is a great investment in your future.
When you fully engage with your work, magical things happen. You put yourself in a position to brighten the days of your teammates and guests, increase your chances of getting promoted, and are more likely to get noticed by that guest who happens to work in the field you’d like to be in.
You also become the kind of person who does quality work—a person that other people can count on. And that says more about your character than the job you have or the title on your business card.
Right now, at this moment, this is the best job you can get. You should be proud to have it.
Cleaning out my garage, I was confronted by my old barista competition trophies. (yes, barista competitions are a real thing) Winning these trophies meant the world to me at the time, and now they’re this annoying mess I shuffle around every time I clean because I don’t want to display them, but I can’t bring myself to throw them away.
I used to think I kept them because I was proud of the achievements, which I am, but I think more so they're a reminder. They remind me that I can do new things. They remind me that I can reinvent myself. And they remind me of the people who helped me do so.
They remind me of Tony who introduced me to a slice of the industry I didn’t even know existed. (in a pre-social media world, this was literally life-changing)
They remind me of Andy who let me use his practice space and gave me coffee to compete with even though I didn’t know him well and had no track record.
They remind me of Eileen who hired and supported a quirky small-town kid who didn’t quite fit in.
They remind me of Ryan and Gabe who pulled all-nighters helping me prepare while Drew kept me on my toes.
They remind me of Duane giving me his number and meeting me at the Annex to cup coffee with me for some reason that I still can’t begin to understand.
The list goes on.
You probably don’t know any of these people and that doesn’t matter—what matters is what my dusty trophy shelf showed me.
We all have something special inside us, and while we have to put in the work to unlock our gifts, there are people out there who can help us be more of who we are than we ever could be alone.
There are millions of ways to make a contribution and impact the lives of others. Most of them don't come with trophies. Career opportunities for a superstar barista are limited, but helpers will always be in high demand.
The real trophies are our experiences. The most important thing to us in one season of life can be an afterthought in another. Nobody cares that I have a useless pile of wood and steel proving that I can make coffee really well, but the experiences they represent are priceless.
Your unique voice and point of view are irreplaceable, but your position is a different story. If you leave, someone will fill your slot, they might be more or less capable, and they won’t do what you did the way you did it, but some version of the job will get done.
Instead of seeing this as a negative thing: “I can be replaced at any time”, we can choose to see it as a positive thing: “If at any time this isn’t working for me, I have the freedom to seek out something that is.”
How many times have we seen people stay in toxic situations because of some misplaced sense of responsibility or ego? “My team needs me” or “This place is such a mess and I’m the glue that’s holding it together” or “I’m the only reason people come here.”
If you’ve been at your post for 1, 3, or 5 years and you truly are the only person holding everything together, that doesn’t speak very well for your workplace culture or your ability to impact the lives of the people around you. While there is some value to being a diamond in the rough, there’s much more value in being able to create more diamonds.
So if you don’t have enough influence to create the change you hope to make inside your current organization (I’ve been there), it might be time to cash in on that replaceability and find or create a space where your gifts can fully shine.
The people you’re worried about leaving in a tight spot might miss you, but they’ll be fine without you. Zoom out 5 or 10 years and this is easy to see. The harder part is being honest when asking yourself the following: Are you staying because you owe it to everyone around you, or are you simply using that as an excuse?
People simply feeling good at work isn’t a sign of a healthy culture. Feelings are fickle and often the so-called '“happy ones” are the only ones we give credit to. If everyone is happy all the time, we must be doing our job well right?
But when we’re deeply engaged with something we care about and understand the potential impact of what we’re doing (how our work connects us more deeply with other people and ourselves), we dive deep into the emotional well.
All the projects I look back on with pride were accompanied by a process riddled with pain, frustration, anxiety, and fear. This isn’t to say I don’t enjoy the creative process, I do, but that enjoyment is a multidimensional thing. Sometimes we feel good while we’re creating and sometimes we don’t. The good news is our feelings don’t dictate our impact and don’t have the power to derail our process unless we give them that power.
A culture that focuses only on feeling good is less healthy and will ultimately be less effective in executing its mission than a culture that helps people acknowledge and embrace the entire range of emotions that come with doing something that matters.
When we opened Cat & Cloud we hired eight people. It wasn’t a stretch for me to look at those eight people and imagine that one day they could retire with us. I wasn’t sure how it would work, but it felt reasonable—if they grew as the organization grew, they could have lifelong careers with us.
Six years later our upper leadership team is exactly eight people. Two of them have been with us since day one but most of them were brought into the fold at different points on our journey.
We currently have seventy employees, and it’s much more difficult for me to look at those seventy people and imagine they could all retire with us. Not because of some size cap we have but because our pace of growth considering our resources (we don’t have huge amounts of external funding), and standards (quite high), make us more of the tortoise than the hare.
It’s tempting to try and solve the lifelong career equation. What kind of growth would be necessary to provide an A-Z path for everyone on staff at all times? Since that equation spins the growth flywheel, it’s easy to see how the numbers scale exponentially—if we solve for seventy, we’re faced with a problem of hundreds and then thousands.
This also makes a lot of assumptions. It assumes that everyone who experiences what we have to offer would decide to stay. That every person, each one with their own hopes and dreams, will discover that the best place to bring their dreams to life is with our organization. As business owners we tend to be proud of what we’ve created, and rightfully so, but it’s a bit egomaniacal to think this way.
Shuffling the Deck
Although people start companies, I’ve always found individuals to be far more interesting than organizations. Maybe it’s the compromises that come with the realities of business or that chasing popularity and growth tends to (counterproductively) water down a strong point of view. I feel a world in which more people are speaking directly about what they believe in and can do it in a financially viable way is richer than a world in which we all work for “Big Corporation X”.
Don’t get me wrong, there’s a place for the big. I like that Disney has the resources and team to be able to create Frozen II, but for me, this is more of an exception than the rule. Small is personable, small has a point of view, small is nimble, and small in size doesn’t mean small in impact.
Taking into account all of the above, it’s clear what our opportunity is.
We can choose to be a place of growth. A place where people can learn about themselves, learn skills that will help them on their journey, and learn what it means to be of service. A place where people can see the magic of their contribution and begin to realize their potential.
For most people who walk through our doors, we’re more of an incubator than a forever home. This isn’t a trivial role to play—the experiences we create for the people around us shape our lives and theirs. The journey matters.
A certain percentage of people will stay. The journey on offer and the journey they’re looking for will be a perfect fit. This blows me away. The fact that we’ve created a place that someone wants to make their forever home is incredible.
People will always leave. As business owners, part of our challenge is to embrace the fact that keeping people isn’t as important as helping them find their voice and ultimately their happiness.
If we’re doing it right, every time the deck shuffles we’ll draw a better hand than before.
“And now we get to officially start this company for real.”
This is something my business partner says when we discover a way to push past something that’s been holding us back.
This happens often so the phrase gets thrown around often.
I was poking fun at him yesterday after a brainstorming meeting: “You say that every week!” It felt even more ridiculous given this Friday is Cat & Cloud’s sixth birthday.
It made me chuckle and reminded me that today, right now, is a moment you can decide to do something you’ve been meaning to do, say something you’ve been meaning to say, and be who you ought to be.
The opportunity in front of you doesn’t care if you’re how old you are or how long you’ve been in business. Every day you can make the choice to embrace that opportunity or not.
I made a video to commemorate Cat & Cloud's sixth birthday. Get a peek inside all our locations, some fun flashbacks, and a look at WHY we do what we do.
The question isn’t: Will there be problems?
The question is: When you notice a problem, what are you going to do about it?
Paths to consider:
Taking Action To Fix A Problem
Empowers you
Makes the problem your responsibility (even if it’s not your fault)
Problem gets solved
Life is better for you, your team, and your guests
Complaining About A Problem
Strips you of your agency
Makes the problem someone else's responsibility
Problem still exists
Life hasn’t changed for you or anyone around you
I’ve been guilty of being the complainer in the past, and while complaining gives the illusion of productivity in the short term, it’s not a great strategy for making things better.
Sometimes ignoring the problem is the best solution for the time being. Multiple problems always exist and some need to be actively ignored so we can focus on what’s most important.
So while noting, logging, and ignoring is a viable option, simply complaining without offering a path to improvement is selling yourself short.
We all have blind spots so a certain amount of truth-telling is necessary to improve, but if you only ever bring problems to the table and not solutions, you might be the one with the biggest problem.
I created my first crude cafe business plan in 2005. Cat & Cloud’s first retail store opened in 2016. At some point in this time window I knew enough to get started but didn't believe in myself enough to follow through.
There were other factors in creating something that worked—my great business partners for example. But I’d known them for years at this point. It’s not like they weren’t around, it’s that they couldn’t appear as business partners until the choice was made to start the business.
So while a certain level of expertise is needed to create impact, if you find yourself continually stalling on your projects, it’s prudent to ask yourself if you’re preparing or simply avoiding responsibility.
Two things stick out to me here:
1. You get to pick your pain. The pain of moving forward despite the uncertainty (that hurts now), or the pain of not trying (that hurts later).
2. The only way to honor your future self is by trusting your current self.
A package deal.
I’ve gambled with my reputation by creating garbage and it usually doesn’t go well. On the rare occasion that it does, it still doesn’t feel satisfying.
So two questions I’ve learned to ask myself before taking action are: Who do I want to help, and who do I want to be?
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