Being in the coffee industry, I love telling the story of the morning. People get up, shower, eat and head out to start their day with the beautiful tradition of morning coffee, so on any given day, the first person they interact with outside of their house is the person at the coffee shop.
That first interaction sets the tone for the day, and we're grateful to be in a position to set someone's day off in a positive way.
Your circumstances may be different but every one of us has the power to create experiences that can change someone’s world for the better. When we pass on positive energy, people carry around that energy with them long after the interaction is over and feel inspired to pay it forward to others.
It doesn't matter if you're the CEO of a huge organization or a dishwasher at McDonald's (proud alumni here), there’s no authority, permission, or money required—you already have everything you need inside you.
The trick is to see beyond the what and into the why. You might be making coffee, flipping burgers, or building spreadsheets, but at some point, everything you do connects in a way that transcends the product. How that connection lands is up to you.
Your work matters. Respect it.
Which feels more sustainable:
Trusting your team to move forward, however imperfectly, before they are ready.
The nonstop stress that comes with trying to do everything yourself.
Owning your losses gives your team freedom to own theirs. Trust goes up, the environment becomes safer, creativity is sparked, and people can put the fear of failure aside and focus on doing good work.
Attempting to hide your losses teaches your team that they should hide theirs. Trust goes down, the environment quickly becomes toxic, creativity is choked, and the fear of failure pushes people to become more concerned with looking good than actually being good.
If we’re going to play basketball, there are certain rules that come along with the game. Everyone agrees on those rules and as long as we respect them, we have tons of freedom to maneuver as individuals within those rules.
Without rules, we can’t appreciate the skill of the players. No matter how good of a ball handler someone might be, dribbling out of bounds to get to the basket is neither impressive nor effective.
Intentionally created workplace cultures have the same effect. Rather than boxing people in, a shared sense of purpose and a common language empowers employees to engage in critical thinking and be creative, not simply read task lists.
Almost paradoxically, channeling our creative energy within a framework leads to more interesting ideas than an unfocused creative free-for-all.
Some aspects of life are layered—we build on our past and add another brick to the wall.
Some aspects of life are transitional—as new doors open, others close behind us.
It’s often difficult for me to appreciate the good that’s happening around me in the moment. I’m poisoned by wanting more, by the desire to get to the next level.
For all the progress I’ve made, it’s not clear that I’m in a better place than I used to be. A different place, yes. But better? I’m not so sure.
Looking back on the experiences I’ve had on this journey it’s clear to me that each phase of our life is special and imperfect.
As much as each moment can be a springboard to our future, it's important to remember that we're actually living right now. Maybe you started a big project today, opened a new location for your business, or pushed through another day of pain.
It'll never be quite like this again and that's both scary and empowering. Try to enjoy it.
Our culture sees feedback in the workplace as synonymous with getting in trouble. This is probably because most people (myself included) have had less than stellar experiences with feedback.
My favorite experience was when the store director at a previous job asked me if I was too fucking stoned to stock our retail shelves in a timely manner. More of an outburst than feedback, this resulted in me immediately walking behind the counter to grab my coffee cup and backpack and head straight for the door. (I’m really good at walking out on jobs.)
Everybody left feeling worse that day. The store director didn't get what she wanted, and I had to go find a new job. Thankfully, there is a better way.
Building Bridges
Ongoing constructive feedback builds a bridge between the employee and the employer. When both parties know exactly what’s on the table and communication is constantly flowing, it’s easier to focus on your work. Work becomes more relaxing, even if you’re really cranking. Constant conversations build the relationship, and there's an ease in knowing exactly where you stand.
In addition to protecting your culture, consistent feedback acts as a pressure release valve. The tension never gets built up enough to spur a childish outburst that leaves you and your employee feeling worse than you felt before. Pro tip: berating people doesn't inspire anyone to do their best work.
So no, you’re not in trouble. This is an opportunity for two players on the same team to connect and get better. Take advantage of it.
Tomorrow Cat & Cloud turns five.
I feel compelled to send a laser beam of gratitude to my business partners. As I’m sure it is with me, their most positive attributes are also the most challenging to work with.
Jared moves forward with what feels like reckless optimism.
Charles supplies an endless bummer of reality checks.
I have uncompromisingly high standards to the point of being destructive.
Because we’re willing to accept each other's quirks along with the gifts, we’ve created a space in which we know that anything is possible, can turn dreams into reality, and do work we’re proud of.
Maybe it's not about accepting the quirks along with the gifts, maybe it's about recognizing that the quirks are the gifts.
I’m grateful for both of you. Cheers to five years!
Yesterday I shredded my last copy of an old orientation manual I had lying around.
This spiral-bound workbook on thick card stock stuffed full of definitions, graphs, and worksheets, wrapped in our brand's color palette was the accompaniment to our three-hour orientation process.
We touched on our company history, service model, mission, vision, values, coffee tasting, coffee processing, benefits packages, how to craft a pitch to bring a new idea to the table, and the list goes on.
Laughably, this was scaled-down compared to orientations we’d used at previous organizations. We thought we were keeping it simple, but it was a tidal wave of indigestible information.
As ineffectual as it was, it took us years to shake that model, partially because having a big fancy orientation made us feel like a big fancy organization.
Our goals with orientation are:
Introduce you to our mission, vision, and five values
Set expectations for the employee/employer agreement
Leave you feeling inspired
Our orientation is currently a one-hour, conversational gathering with no booklets, slideshows, or videos. By focusing on delivering on our promise rather than maintaining a certain appearance, we’re able to accomplish our goals and make the experience more enjoyable to boot.
It’s the difference between doing the work and making it look like you’re doing the work. They both take effort but only one pays off.
We spend so much time and energy trying to convince people who don’t get it.
Perhaps what we should be doing is finding people who already do.
Every once in a while it feels right to recalibrate the compass.
I hesitate to put a flag in the ground and proclaim “this is why we’re here” because I don’t want to limit the ideas I explore. That being said, a good portion of the work that’s stacking up is pointing in a certain direction.
I thought: If I had to write a trailer episode for this blog, what would it say? (It’s a more drawn-out way of asking the question: “Why are we here?”)
This is where my heart and brain are leading me:
This I Believe
Businesses shape the cultures we live in. They’re the cultural glue for shared experiences and set the stage for most of our day-to-day interactions. We engage with businesses every day as customers or owners, but especially as employees. We spend a huge chunk of our waking hours at work and our experience there shapes our lives.
But work is broken.
We live in a world where it’s normal for employees to talk trash about their bosses, and bosses view their employees as a necessary evil. Instead of tapping into the potential of work, we see it as simply a means to an end. It’s a lose-lose for both parties, and our culture is the collateral damage.
Businesses are at their best when there are people taking ownership at every level. This only happens when there’s a common language, shared sense of purpose, and a culture that encourages this style of work. But these cultures don’t happen by accident, they’re created.
As leaders, it’s our responsibility to set the tone and create the environment, but stepping into that responsibility isn’t easy. Leadership can often feel lonely, stressful, and more like a punishment than the opportunity it is.
This is a space to explore that opportunity.
I dream of a world in which people find joy in the work they do. A world where work is a place to embrace challenges, create, and grow while contributing to something bigger than yourself.
If you’re not a business owner or manager, that’s ok. Leadership isn’t about a job title, it’s about sharing your gifts to lift up the people around you.
It’s an opportunity we all have. So let’s get to work.
When I was working behind the counter, measuring my impact was simpler. I could feel the change in someone’s body language or see their eyes light up when we interacted.
They might even say:
“I really appreciate you, this sets the tone for the rest of my day. Thank you.”
The further away from that world I travel, the murkier the waters become.
I’m no longer that experience factory pumping out 2 minutes of magic for each of the hundreds of people I’d serve each day.
It’s more nuanced now. I connect with fewer people face to face. Instead of blasting people with my energy cannon, I spend my time listening, asking questions, and planting seeds that other people will water and grow with time.
Gone is the instant gratification of guest service. I create and share in hopes of making things better and helping others who are on a similar path.
Maybe I can shorten someone's learning curve. Maybe I can empower someone to take the first step towards something that everyone else is telling them is impossible. Maybe the people around me will grow into amazing leaders and maybe I'll have played some small role in that journey.
I hope all of these things are true. But I can’t be sure. It’s a strange feeling.
When someone asks me: “What are you working on today?” I often don’t know what to say.
Describing my work in list format makes me feel like I’m not doing enough.
“I’m going to have some conversations, mostly listen and ask questions, maybe go for a walk and think about what would make Cat & Cloud the best place to work ever, then call Jared and kick that ball around for a while. How bout you?”
I watch from the sidelines as our employees make our guests' eyes light up, one after another.
When I step back and watch the show I become aware that in so many ways I’m not who I used to be, and I’m not quite accustomed to being who I am, but I’m looking forward to growing into it.
Part 1: Leadership Anxiety
I love visiting our stores, but I haven’t always.
Going into our stores used to give me intense anxiety and was a very unfulfilling experience for me.
The feeling of not wanting to go into your own store, a place where you put a ton of effort into creating amazing experiences for other people is a weird one, but also a feeling many business owners have told me they experience as well.
“So what is it?” I ask them, “What makes you feel so uncomfortable in a space that you’ve created?”
There are many different answers but each person I’ve spoken with intuitively knows something is wrong, and is often too afraid or feels too unprepared to take action on it.
I get it. It can feel like a lot. The gap between the vision in your head and reality is huge. But you need to try. Take it one small step at a time. It might take years. YEARS.
We opened Cat & Cloud in 2016 and just in this last year I’ve been starting to feel like this is my home. I’ve always believed in our potential, even when the stress was eating me alive, now I have that belief and the love that comes from doing the hard work. (Starting a business is the easy part)
So let’s get after it. I know you’re tired and mentally stretched but what good is spending all your time and energy building something you can’t even enjoy?
Part 2: The Best Piece of Advice
I posted the above to Instagram earlier this week and received a great question:
“What’s the best piece of advice you can offer shop owners and managers experiencing this?”
While I’m pretty sure there’s no one best piece of advice for anything, this is what came to mind:
It’s ok to admit when you’re not getting any joy out of the work we’re doing.
This doesn’t mean you’re not cut out to be in leadership. It could mean you lack a clear understanding of what you want, don’t share common goals with the people around you, unknowingly adopted someone's broken system and narrative for how work gets done, and the list goes on.
Owning that something is wrong and knowing that something isn’t some inherent flaw in who you are as a person gives you power. Power to experiment, look at old problems from a new perspective, and get specific on what you’re doing and why you’re doing it.
This isn’t possible if you continue to hide your pain behind the smile you’ve been forcing yourself to wear.
Justifying is a defense mechanism we employ when we don’t trust the people around us, haven’t articulated a clear sense of purpose, or perhaps don't trust or believe in ourselves.
Over time, distance is created, and we feel the need to justify more and more because we have no common language or shared goal—our team doesn’t understand the culture we’re trying to create or how they can contribute to it.
Contextualizing is an educational gesture that ties a golden thread from our decisions to our culture and the people who reinforce that culture.
Over time, connection is built, and we need to contextualize less often because we have a common language and shared goal—our team trusts our intent and can connect the dots between our decisions and the cultural benefits on their own.
Which world do you want to live in?
I’ve never had the perfect boss. Looking back on it now, some of my bosses had so little experience it seems laughable. Despite their imperfection and lack of experience, the bosses that had the biggest impact on me all shared three qualities:
Belief in a greater mission or purpose
Belief in the people around them
Consistently taking action to improve
Great employees also seem to share these qualities. While I've worked with many great employees, I have yet to work with any perfect ones.
Imperfection isn't an excuse—at some point, a certain level of competence is needed to be an effective leader or employee. What level of competence are we willing to accept? That's a tricky question; there's some matrix of the three attributes listed above, a gut feeling about that person's intent, and our personal needs.
In the case of continued annoyance at the imperfection of others, it's healthy to consider your role in your discontent.
If you've had multiple terrible bosses in a row, it could be that you're the problem.
If all your employees are lackluster, whose fault might that be?
Unattainable expectations create cultures that feel unsafe. Unsafe cultures stifle growth, learning, and creativity. We can point out imperfections all day and go nowhere but what's the point?
While you'll never find the perfect boss or employee, you’ll also never find the perfect friend or partner. I'd be willing to bet your life is full of people who make it richer despite their imperfections.
Employee Loop
If we don’t know what will work, but we know what we’re doing isn’t working, we have a choice: Keep doing what we know isn’t working, or experiment with something we think will work, even if we’re unsure.
It sounds like an obvious choice until you add fear and stress into the equation.
We know we’re stuck but we also know exactly how being stuck here feels, and there’s some comfort in that.
If we set out on a new path and it doesn’t pan out—is the lost time and energy worth it?
If we try and try again, and come up short multiple times in a row—what does that say about us?
Cultural Loop
Most workplaces aren’t known for being safe places to experiment. Broken workplace cultures actively feed our fears (and probably created a great deal of them in the first place).
Clock in. Do what we tell you. Clock out.
Want to get ahead? Great. Do what we tell you faster.
If you do something off-script, maybe you get fired.
We can’t expect cultures that punish thoughtful trial and error to be breeding grounds for creative problem-solving.
Leadership Loop
The nuance that separates thoughtful, culturally aligned experimentation from simply doing things because you had an idea and thought it was cool, takes a lot of time and energy to tease out and train, so we (business owners, leaders, managers) avoid the work, creating our own loop.
We don’t have a culture that brings the best out of our people but we feel comfortable with our energy input and we know what to expect. Despite our cultural shortcomings, we feel safe. We rationalize sacrificing what could be to maintain the seemingly delicate balance of what is, even if it’s not working. (Sound familiar?)
Hope is a more charming driver than fear, but if we’re going to let fear weigh in, it serves us better to be afraid of what will happen if we don’t actively evolve, rather than being afraid of what might happen if we do.
Stepping into leadership can be intimidating. You’ve done good work to earn your position yet somehow it feels like you don’t belong or don’t deserve it.
What do you say?
How do you act?
What do leaders do?
Well, that’s complex, but try starting here:
1. Accept that someone put you in a leadership position because they believe in you, and you’ve earned this opportunity. You’re not perfect and neither are the people who are vouching for you (they’re also learning as they go.)
2. Act how you’d want someone leading you to act. Be the leader you’ve always wanted to have. They’re probably not overly aggressive but they’re confident despite their imperfection. They motivate you and push you to be better without belittling you. They listen more than they talk but when they need to speak up, they’re not afraid to do so. You can be that person.
The above are mindset shifts. You'll have to do the work to close the skills gap through practice, but despite what you don't know, you can still set off on your journey with intention.
You don’t have to become a new person because you got promoted. You do have an added layer of responsibility and influence, and weaving who you aspire to be with who you already are is a great way to push forward without losing yourself in the process.
The opportunity to help someone grow is a beautiful thing.
Helping requires openness and patience to walk alongside someone while they find their bearings. Helping also requires understanding and connecting.
This means asking more questions and giving fewer answers. Being more curious and less judgmental. Allowing the time and space for discovery rather than simply barking orders.
We can provide a North Star, we can provide guardrails for course correction, but once we start drawing the map for the people we hope to lead, we rob them of the chance to grow and increase the probability that we’ll have to draw the map for them over and over again. Not because they're not capable, but because we've shown them it's more important to follow orders than to experiment and fail forward.
If we find ourselves constantly needing to give prescriptive commands and micromanage, it probably says less about the ability of the people around us and more about our own shortcomings as a leader.
The great thing is, we’re allowed to give ourselves the same grace we give others and move forward despite our imperfection.
“How did you get started?”
Tricky question.
Did we get started when we roasted our first batch of coffee, hosted our first pop-up, opened a brick & mortar, or when we hired our first employee?
Each of those moments was their own version of getting started.
The truth is, we got started years ago. Paying into the bank of learning a craft while investing in ourselves by showing up with intent. Of course, a craft is only as valuable as its impact on other people, so while we wanted to be better for ourselves, we also wanted to create great memories for others.
Even as I write this today I feel like we’re just getting started. Most days we do something we’ve never done before—giving ourselves the gift of starting over.
How you get started isn’t terribly important, what’s important is that you make the decision to get started.
Intention gives purpose to your actions.
Taking imperfect action pushes your vision forward.
Learning closes the gap between your intention and reality.
Each step in this never-ending cycle is important. Here's the flip side:
Action without intent feels cold and uninspired. If we don't take action, our ideas aren't useful to others, and we won't realize our true potential. Failing to learn from our mistakes and success makes us stagnant (at best).
The evolution of Cat & Cloud is a result of this cycle. We've always had strong ideas and opinions, were comfortable making mistakes, and found energy in learning and growing along the way.
Being perfect is out of the question and ultimately boring, so we're shooting for better.
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