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.

Ask questions to understand, not to judge.

Employees: Your boss used to be where you are. They have insight and information that you’re not aware of that’s informing their decisions. If there's something you can't piece together, asking for clarity makes you more effective and connected.

Bosses: Things that are obvious to you might not be obvious to your employees. Taking the time to explain the why behind your decisions empowers your employees, and creates a learning moment. If your people are struggling, asking for clarity on what's been challenging in their world gives you valuable perspective.

Asking with positive intent is much different than asking with a "prove it to me" mentality. Genuine curiosity builds trust; asking in judgment pushes us further apart.

It's not always easy to embrace what we discover. Sometimes our conversations reveal that the issue isn't with the system or the other parties involved, but ourselves. Even so, we're all better off for having the conversation.

Us vs. them cultures foster stress, aren't fun or rewarding, and don't inspire us to share our gifts to the fullest. This shouldn't be the stage on which we spend the bulk of our waking lives.

We're all on the same team.

A week away from work feels like an eternity.

What did I miss?
Did everyone move on without me?
Am I even necessary?

At Cat & Cloud, when we first earned enough freedom to take a bit of time away here and there, the above feelings came with a side serving of guilt.

It’s been a process to erase those feelings, and there are many factors at play, but nothing has made me feel more confident about taking time away than the strength of our leadership team.

Their growth and the consequent growth of those around them have made my vacations stress-free, a nice perk to be sure, but the real gift they’ve given me is making the day-to-day project of running a business so much more enjoyable.

Business owners or not, we all need a support group. Family, friends, neighbors. People we have the privilege of sharing our lives with. People that make every day amazing. Having someone to feed the cat when we’re gone is just a bonus.

Only a small amount of life happens while we’re on vacation. Working for the weekend is a misplaced ideal. The real fun is right here, right now, day in and day out.

The people around us are not a means to an end in our lives, they are our lives.

The other day one of our newer roasters asked me if I’d ever roasted coffee.

This made me chuckle a bit, as when we opened, I roasted about 90% of our coffee. I lived right around the corner from our first shop and although we were just getting started, keeping up often required me to show up at night solo to roast solo while the neighborhood around me slept.

It’s been a while since I’ve stood behind the roaster. Long enough now that our new and even not so new employees don’t know that I have that skill in my bag.

This brought up conflicting feelings. The positive feelings associated with progress, both personally and professionally, and the slight sting that comes with not being seen as the expert at the skill you spent so much time, energy, and effort building.

There’s the paradox. I can’t think of anything more annoying than in ten years being known as simply “the coffee guy” yet It’d be really nice if I could be the new version of me while simultaneously still being the coffee guy.

So if I’m not who I was, but I’m not yet who I want to be, who am I?

You

While it would be neat and tidy to project our worth through the singular lens of what we do, this creates a warped picture of who we are.

Our past success is important, as is our future potential, and we have to carefully navigate this balance. Holding on too tightly to what was, prevents us from moving forward. Letting go too easily prevents us from building on our past achievements. But the journey is forever and at no point can we point to our current job title, award, or skill we’ve developed and say “This is me.”

On our journey, the job we have is less important than how we show up to that job. The number of friends we have is less important than how we show up for the friends we do. The skills we develop are less important than the process that led to attaining those skills.

The value others may assign to you because of your status and the perks that come along with that status are nice, but these perks are as temporary as that status. Some seasons come with more prestige and clarity than others but throughout all of them, you are still you.

One of the questions we ask at new hire orientation is some version of: “Tell us about a time you had a memorable experience that stuck with you.”

The prompt catches some people off guard, partially because it can be nerve-wracking to share stories with a group of people who just hired you, and partially because of the pressure people put on themselves to generate these fantastic stories.

Sometimes people get stuck and we have to grease the wheels with a memorable experience of our own. This is my most recent example:

Last week my cousins came to Santa Cruz for a birthday celebration and invited us to hang at their BnB, which was a stone's throw from the beach. It was a holiday weekend which makes anything near the water a complete disaster for parking.

We pulled into a packed pay lot with a train of cars all playing an automotive version of musical chairs, stalking pedestrians with fingers crossed hoping they would jump into the car right in front of us and we could slide into their spot.

After a few trips around the lot we got lucky–a family packed into the car right in front of us. We stopped and waited patiently (strollers, ice chests, and two small children take a while to load up).

Before the car pulled out, the woman driving hopped out, walked up to our window and handed us a small ticket.

“I paid for all-day parking so I figured this will make your trip just a bit easier.”

She handed us her ticket to display in our window.

Would it have ruined our day to have to shell out the $10 for parking? No.
Would a trip across the lot to the pay station have killed us? No.
Was it incredibly inconvenient for her to walk the five steps to the car and hand us the ticket? No.

But it made me smile, and I couldn’t help thinking that if everyone else I’d interacted with that day was that thoughtful, how all those seemingly small interactions would have made my day so much more pleasant.

I also had to ponder the question: Would I have done the same thing if our roles were reversed?

Now we can see the purpose of this exercise.

First, to note what it feels like when someone gives us the gift of a memorable experience, (this makes it more likely that we will want to do the same for others).

Second, to understand the power we have to improve someone's day despite not having any formal position of authority.

Every person in every position at our organization has a conduit through which to lift up another person. Even those who are not guest-facing work with a team and create products that deliver an experience.

You have this opportunity as well. It may not be built into the DNA of your workplace or even encouraged, but you can still choose to show up and go above and beyond. To connect. To inspire. To create these seemingly small moments of awesome that aren’t really small at all. It’s these moments that shape the tone of our days, seasons, lives, and the lives of those around us.

We shouldn't take them for granted.

We all have our reasons for avoiding the difficult, slow, and meaningful work we should be doing. Here are a few of mine:

• Fear of lost time: This project will take a while–will it be worth the time I invest?

• Fear of judgment: This project feels incredibly personal to me–will other people think it’s stupid?

• Fear of failure: There’s a lot riding on this project–what happens if it doesn’t work out?

These fears visit me often. They make me second guess myself, my knowledge, and my ideas.

Everything from a deep understanding of my Why and the contribution I hope to make with my work, to the latest and greatest time management hacks and productivity boosters, can’t keep the fear away.

So I fight. Wrestling with the fear that comes from the projects I should be working on, and the self-induced anxiety of needing to show constant proof of my progress. Weighing the fear of sacrificing my best work to simply be busy, with the fear of lost time, judgment, and failure.

This is the part where an expert would have the answer. Well, I’m not an expert and I don’t know what will work for you.

What I do know is my most rewarding work has come when I’ve accepted my fear and moved forward despite it. That when I set aside the need to do everything, be everything, and constantly prove that I’m valuable, and instead move forward on the right things, I’m always rewarded, even when the thing I’m working on doesn’t work out.

As a business owner, it’s easy to get caught up in the number of things about our organizations that are imperfect. The gap between the vision we see in our heads and reality is never-ending, and we see dozens of opportunities for improvement every day. That’s our gift and our curse.

We see opportunity. But there's a blurry line between opportunities and problems.

We take action. But there’s a blurry line between action and reaction.

How we frame these imperfections not only affects what we choose to work on but how we feel.

I can’t help but notice how defeated I feel when I see our organization only as a collection of problems that need to be fixed.

It’s not too different from the way I feel about myself in those low moments when all I can think about are the things I haven’t accomplished. That’s another blurry line–the blurry line between seeing yourself as having potential and seeing yourself as someone who never quite gets it right.

While it’s important to recognize and honor our potential, walking around all day feeling terrible about who we aren’t or what we haven’t created isn’t incredibly useful.

Professionally there will always be a gap between our vision and reality, just as personally there will always be a gap between our potential and our ability.

We can’t close the gap, but we can control how we view the gap and take action on it.

Each position we occupy comes with both limitations and opportunities. As my role has shifted from barista to business owner and everything in between, so have my limitations and opportunities shifted.

At each stage, it’s tempting to see the limitations of your position as the things that define you, your contribution, and your ability to learn and grow. These limitations make it easy to complain about what we don’t get from our jobs, our family, or our friends. But framing everything in terms of limitations ignores the possibility that’s in front of us all.

Employee

As an employee you have less creative input and can’t drive the direction of the company, but you can impact every person on the other side of the counter in a positive way–give them energy that they can carry around with them for the rest of their day.

You can show up with the intention to work on your interpersonal communication skills, giving and receiving feedback, detaching and seeing things through the guest's eyes, learning about the structure of the business (labor models, margins, etc.). There are an infinite number of things to learn in any position and you don’t need permission to start.

Employer

As a business owner I have more creative input and the power to steer the ship in the right direction, but I feel the weight of everything that’s happening in a way that’s not easy to turn off or set aside until the next workday.

Business owners have my favorite excuses for focusing only on limitations: I’m too busy and can’t get ahead, creating a mission-driven workplace culture might work for some companies but it won’t work for ours, all my employees are lazy and unmotivated.

Bridging The Gap

Whether you’re the employee or the employer, your growth hinges on your willingness to take action on the opportunities you have, and not use your limitations as excuses.

Don’t wait until you have a great boss to be a great employee.

Don’t wait until you have great employees to be a great boss.

We often see the process as the necessary evil we have to trudge through to get to the outcome–the dream we have or vision we see in our heads. But it's really the other way around. That dream we have is actually the spark that inspires us to embark on the beautiful journey that is the process.

Sometimes our dreams come true only to have us realize we've evolved and our dreams have changed. Sometimes we set out to build one thing, take a detour along the way, and end up with something greater than we ever could have imagined.

And what happens when we've achieved our outcome, intended or accidental? We can't stay there. Basking in our accomplishments only puts us behind. Not behind other people, but behind our own potential, behind the possibilities locked within ourselves.

It's important to recognize your wins. Celebrate with friends or get yourself a present, but then you have to move forward. You have to get back to the process. This is where the magic is. This is where things happen.

Day by day.
Brick by brick.
We build.
We create.
We laugh.
We cry.
It's a roller coaster.

Sometimes we want to quit. But we can't. Because we know that honoring the process is honoring ourselves, everyone who believes in us, and everyone who could be touched by the gift we have to share with the world. So we push forward.

Outcomes come and go but process is forever.

Some days the words flow. This isn’t one of those days.

Currently, my brain feels like a spiderweb of a thousand tangled ideas, none of which I can articulate well at the moment.

I’m a perfectionist by nature and have a huge fear of my ideas being misinterpreted. When this manifests positively, it leads to thoughtful work that I’m proud of. When it manifests negatively, I get trapped in my head and create nothing at all.

But choosing to make nothing just because I can’t make something perfect is a cop-out. It’s lazy. It doesn’t serve me or the people around me.

I know when I go to sleep tonight, the pain I might feel from making something imperfect will be less than the pain I’d feel from making nothing at all.

So if you’re feeling stuck, I feel you. Here’s me unsticking myself with something less than perfect. Taking the smallest step in the right direction.

Not every at-bat will be a home run. Some days we strikeout, but when we commit to showing up and playing the game, the benefits over time are undeniable.

I have a fellow coffee shop owner friend whose favorite phrase is “spin off cash.” Once we get to a certain daily average the business will spin off cash. Once we reach a certain wholesale threshold we’ll start to spin off cash. I’ve been working really hard but it’ll be worth it once we start spinning off cash.

“Spin off cash” has become their unofficial mission statement. Now, I’m guessing the cash isn’t really what they want. It’s a signal of something else: perhaps freedom, a certain lifestyle, distance between them and day-to-day operations, or a cultural signifier of success.

A metric of success like spinning off cash could lead you to do all kinds of unsavory things. Cut labor to the bare minimum to keep expenses and payroll low, cut corners on training, pass off a mediocre product as a great one, engaging in one-sided relationships, or fostering a low-trust work environment. These things don't live in a vacuum, they affect the guest, employee, and ownership experience.

For my friend, it manifests itself as a low trust work environment. They end up running around doing all kinds of mundane tasks because they don’t trust other people to take ownership of them. This is their work.

At Cat & Cloud, our mission is “To inspire connection by creating memorable experiences.” We believe in the power of each person to create better and to inspire others to do the same.

The decision to build an organization with this at its core has effects. We expend a huge amount of energy in emotional labor, we work incredibly hard to see things from our guest's point of view, and we often see potential in people that they don’t see in themselves. Our vision is larger than our skillset, so we’re constantly pushing ourselves in addition to trying to empower others. It’s sometimes frustrating and the work is hard but rewarding.

The amazing thing is my friend and I both work equally as hard–our energy output is the same, but the work we do is completely different.

When we choose our metrics of success, we’re choosing the work we get to do and how we view our time at work. This is true for the boss, the entrepreneur, the project starter, and the employee.

What do you want out of work? What are you building towards? How would you like to impact the lives of others?

Choose your metrics of success, choose your work.

We used to have a toxic feedback and coaching pattern at our organization. It went something like this:

Someone would miss. We’d get frustrated and vent with each other as a leadership group. After sometimes hours of conversation about what might be causing the problem and how best to maneuver through it, we’d discover that no one had actually spoken with the person in question about their performance at all. Repeat.

It wasn’t uncommon for us to have five or six talks about a person before actually speaking with the person.

It wasn’t always intentional. Often each miss seemed so small and isolated that it didn’t feel worth the emotional labor of having a conversation, or it was annoying to have to speak on things that felt so obvious. “Why don’t they know this already?!”

So small thing after small thing piled up. Each noticed in the moment but never addressed. These small shifts off-course compound over time for both the employee and the employer.

The employee goes further and further in the wrong direction. The longer someone is off-course, the harder it is to bring someone back. Two or three degrees off-course for months or years requires a huge realignment. When you do address the problem at that point you’re not only addressing behavior, you’re creating a cultural dissonance and changing the reality of what work is.

“Oh, you’ve been doing that for two years? Yeah, we don’t do that here.”

“Actually we do. I’ve been doing it like this for two years.”

On the leadership end, avoiding feedback brews a deep-seated resentment of that person. If you have an employee that is having issues, and a 15-minute chunk of each of your meetings is spent talking about that employee, you probably aren’t going to like them very much or treat them as well as you should. You’re likely to discount them even more and perpetuate the cycle.

After enough time (it doesn’t take long) the misses are forgotten and replaced by these big sweeping feelings. I feel this person may be a bad fit for us. I feel like this person doesn’t care. I feel annoyed whenever I see this person.

Now, feelings do matter. One of the biggest lessons I’ve learned in the past five years is that trusting my gut is really, really important. But given enough time with no guidance or feedback, most people will fall into this category of being a resented employee.

So to fix the problem you have to start looking inward. Yes, we’ll all have employees that aren’t great fits, we’ll all make hiring mistakes, and have to let people go. But if you’re constantly surrounded by low-performing, unengaged people who you have no desire to be around, at some point that stops being their fault and starts being yours.

A curious mindset is easy to cultivate early on. We don’t know much, so in an effort to close the gap between where we’re at and where we want to be, we explore. We experiment. We try ridiculous things often with ridiculous results, but sometimes we’re pleasantly surprised.

As we gain more and more skill, it’s easy to leave the exploration that comes with our curiosity behind. Our work becomes less of an art and more like plugging in a formula.

This isn’t surprising. Most workplace cultures reward us when things go well and punish us when things go wrong. I’ve struggled with this from the other end as a business owner as well. I’ve worked hard to develop a reputation as someone who can get shit done, so when I try things that don’t work out it can feel like I’m degrading that reputation, letting the team down, and even calling into question my capability to lead.

It’s so easy to forget that one of the reasons I’m in the position to lead is my willingness to experiment and explore.

Formulas do have their place. Constantly reinventing the wheel with everything we do would be overwhelming and unproductive. So the challenge is to discover where our real gifts lie, and within that space figure out a way to continually engage our curiosity and encourage those around us to do the same.

It’s relatively simple to teach someone how to give good service. There's a formula for that. It’s a different level entirely to spark genuine care for the people who walk through your doors, which is the only path to giving great service.

From a leadership perspective, it’s easy to tell your leaders to hold their team accountable and get the job done, but it's a whole different ball game to help foster genuine care and curiosity for the people they hope to lead.

We all clock in for eight hours, however not all eight hours are created equal.

Eight hours where you’re disengaged and grumpy with one eye on the door is a long, slow, unrewarding eight hours

You’re not creating great experiences for the guests you’re interacting with.

You’re not an asset to your organization.

You’re not doing a great job for yourself.

“Who cares? I don’t even like this job. This job is just a placeholder–a temporary stop along the way. I’ll kick things into gear when I get the job I actually want.”

The idea that you’ll show up every day unengaged for years and then, once you get the job you actually want, you’ll magically turn it on and show up as a professional is laughable. Since you’re building a reputation for showing up and doing the bare minimum you likely won’t even get that opportunity. (You might think no one’s watching but as they say, the streets talk.)

If by some stroke of luck you do land your dream job, you won’t be equipped to handle it. Not because you’re not smart enough or don’t have the potential, but because you haven’t built the muscle of doing things that are hard. You haven’t practiced seeing things through the guests' eyes or from the organization's perspective. You have very little practical empathy and are probably also not a great team player. (All of these things are interrelated.)

So we shift our perspective about our eight hours.

We have eight hours to train, to learn, to grow. Eight hours dedicated to leaving the people, places, and projects we touch in a better place than we found them.

This changes everything. Instead of watching the clock to see when our shift ends, we’re immersed in our work. People smile at us. We smile back. Since we’re engaged we begin to connect the dots and see how our work matters. We go home fulfilled even if we’re dead tired.

While we might not have our dream job, we get to build our reputation, interpersonal skills, and the muscle of doing things that are hard–all things that will serve us on the path to that job, and in every other aspect of our life.

Think about it this way: What if you got paid to spend eight hours a day training for your dream job? Most of us have that opportunity right now and we don’t even realize it.

When I first started being “the boss” I put a lot of pressure on myself to have all the answers. That was the key to helping my employees right? Having the answers to their questions.

It feels good to have the answer. We get instant gratification. People see us as the expert. We feel useful. But simply handing out answers puts the outcome before the journey, and the journey is where the magic is.

Our real value as leaders isn’t to have the answer but to ask the questions that allow people to discover the answers for themselves.

This requires us to set our ego aside in the name of helping other people and ultimately strengthening our organization, projects, and ideas. (At the end of the day this makes us stronger too, although it’s less obvious in the moment).

This approach means less instant gratification. We don’t get to jump in, save the day, and feel like a hero for having the best solution.

We might even feel stressed because we can see a great answer and it takes everything we have to resist the urge to simply blurt it out and instead ask a thoughtful question.

The person you help might not even realize that the questions you asked helped guide them. They might think they came up with the solution all on their own.

How great is that?!

To set aside your own need for gratification to empower someone else. Do that enough times and you’ll build a capable team. The goals you have that feel impossible will begin to take shape

Sometimes you'll have to jump in to avert disaster but if you’re doing this over and over again it might be useful to ask yourself why.

So I’m learning to ask better questions and see my role less as the person who has to have all the answers, and more as the person who asks the right questions.