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I work with a lot of people who are trying to change something in their teams, small firms, or large organizations.

 

One of the things I’ve noticed over the years of doing this work is that there can be a tendency to want to make a big, dramatic, “transformational” change in one fell swoop. To take on a new strategy, for example, or to change the culture of a team.

 

My observation is that this approach rarely works, regardless of whether you’re a small enterprise (a few lawyers who run a Trusts and Estates firm, say) or a huge, well-resourced company.

 

Here’s what I’ve seen:

 

1. “People don’t resist change; they resist being changed.”

 

This idea comes from Peter Senge, one of the preeminent writers on learning and change. Dramatic change is, by its nature, imposed on a team or company. Because the team is not invited to discover their own path, they resist change.

 

2. Change can be fast or it can be sticky.

 

Fast change creates a lot of activity very quickly—but that fades. I’ve seen companies spend tens of millions of dollars to convene thousands of managers in a huge conference center to create a shift in culture. Such efforts rarely have a lasting effect. When people go back to their desks, they revert back to their normal behavior. The system supports staying comfortable instead of shifting.

 

The most successful change efforts focus on changing small behaviors in small groups. They recognize that adoption isn’t an “all at once” phenomenon and that the success of one team will help others work toward success, too.

 

3. Appreciate what you do well and don’t stop what you’re doing.

 

Whatever you’ve done to get to this point has worked, at least somewhat (otherwise, you’d be starting something new, not changing something existing)!

 

When we want to change, we often lose sight of what does work. If we want to be more entrepreneurial, for instance, we might start by seeing how our current approach to detailed planning has helped us over the years.

 

Appreciating what happens already also applies to work itself. I was recently working with a business owner who wanted to create a new product to complement his existing services business, so that he could be less involved in the day-to-day of the work. His plan (fantasy?) was to take a month off from his normal responsibilities and create his product.

 

Needless to say, that plan didn’t work—he received a lucrative offer from a consulting client and was drawn back into delivering services. To make the kind of change that he seeks, he’ll have to take a more incremental approach, working a few hours at a time on his product while he keeps his business up and running.

 

What about you? What are the ways you’ve seen change efforts work (and not)?

 

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I’ve written a lot in this space about anxiety and uncertainty which, I think, are good things to get comfortable with.

 

I believe that what is needed to be a successful leader in our modern world is to shift from a stance of knowing to one of curiosity.

 

I recently interviewed my friend and mentor Roger Martin for an upcoming podcast episode. Roger’s just written a great new book called When More Is Not Better about, among other things, how the goal of economic growth has subsumed so many other important aspects of American life.

 

The central idea of the book is that we need to think in terms of systems—something that I both wholeheartedly agree with and something that, in many ways, Roger helped me see earlier in my career.

 

There’s a number of interesting things that happen when you make the shift to thinking in terms of systems, but I’d like to highlight one here: recognizing the importance of balancing feedback loops.

 

Many systems exhibit what’s called homeostasis, a tendency to revert to some default set point. This is often by design. Think about how a thermostat turns on the heat when the temperature is too low and shuts it off when the temperature reaches the goal.

 

But sometimes homeostasis shows up in ways that we don’t always expect.

 

Consider, for example, a manufacturer trying to increase profitability. It might set goals to reduce costs, causing the VP of procurement to source the cheapest raw materials she can find. In most companies, the VP would be rewarded for her work helping the company meet its targets.

 

But, as systems thinkers, our analysis can’t end there. Using cheaper raw materials has a consequence. In the instance I’m thinking of, it introduced quality problems in the finished product and additional waste in the form of raw materials that can’t be used.

 

These consequences—which balance the original efforts to make the system run more cheaply—often happen after a delay. It’s not clear that they’re caused by past choices because they show up as a different problem (one that the VP of quality now has to figure out).

 

This isn’t a concept that just applies to manufacturing. A software company might reduce testing in an effort to get its products out the door faster. Or a law firm might try to save money by reducing the number of support staff—only to see billable hours fall as attorneys have to spend more time managing administrative details.

 

The most successful leaders recognize that every choice represents a point of tension. They consider their system holistically. Their goal isn’t necessarily to be the cheapest or the fastest. Rather, their goal is to learn and experiment with their system. By attending to all its parts, they can balance their goals across a number of dimensions and, ultimately, deliver outstanding value.

 

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It’s the week of the launch of my new podcast, The Breakdown™ with Chris Clearfield, and I find myself feeling anxious about it.

 

For me, that anxiety shows up in a couple of ways.

 

It shows up when I wake up in the middle of the night and can’t go back to sleep.

 

It shows up in my body—back pain, knee pain. Everything feels all akimbo. (This is a good tell for me. I had back pain when I was younger that only went away when I realized it was a sign that I had emotions I could not yet feel or voice.)

 

I’ve been trying to figure out why, and where the anxiety comes from. After all, it’s just a podcast!

 

But there are clues.

 

When I notice my anxiety, it gets stronger. It makes me want to move away from the process. To delay the launch. To postpone it. To say that we are too busy. To, as I say with my partner, “drop the rope,” like walking away from a game of tug-of-war when it gets too hard.

So, where does the anxiety come from?

 

What I’m doing here in my work and my life is, as a well-known journalist I know put it, ploughing new ground.

 

It’s not alien ground—I’m not plowing the Moon or Mars. But it’s new ground for me.

 

There are hundreds of thousands of podcasts out there. Sure. Absolutely.

 

But I’ve never launched a podcast before.

 

I’m anxious because I’m worried that I will fail, that I will look foolish. That I will be rejected, that what I do won’t be “good enough.”

 

I’ve had the good fortune of having a tremendous amount of success in my life. A lot of that stems from privilege—being born a white man at this time in this place. Having educated parents. Social capital.

 

A lot of my success has to do with luck and happenstance. A neighborhood friend who went away to boarding school (the North Carolina School of Science and Math) and made it easier for me to walk that path—and move to environments (first NCSSM, then Harvard) that allowed me to flourish.

 

Some of my success comes from the way my brain works to solve crazy complex problems. By bringing focus. By seeing how the parts come together to form a whole and by seeing the relationships between things.

 

A lot of that goes back to my biology and how I learned to operate growing up—understanding relationships between people helped me stay safe in a world where I didn’t always feel like I fit in.

 

I’ve gotten better with practice. When I studied physics, for example, I was never very good at solving problems by grinding out equations. But I delighted in moving between the details and the big picture.

 

My journey of personal growth started in my thirties when I became a parent. As my son grew, I was able to understand how much I operated in a fixed mindset, one in which I’m defined by my achievements and wary of making mistakes. Now I try to operate in a growth mindset, one in which I acknowledge that the primary pursuit of life is learning. (Carol Dweck’s book changed my life—thank you, Carol!)

This wasn’t just a shift; it was the start of a new journey for me. I’m slowly dropping the stance of self-judgment to one of growth.

 

It’s fun to compare the podcast with Meltdown, about which I never felt much anxiety. I’m immensely proud of the work that András and I did in that book. The writing is tight, the stories are fun, and we take a series of extremely complex concepts and break them down in a way that’s accessible.

 

But writing the book never really felt like a risk. The thing about writing a book is you have a lot of people looking at it. Our editor and team at Penguin Press were fantastic. Our agents were great. We received excellent input from academics and some talented folks like the organizational psychologist Adam Grant.

 

We had a lot of support and a lot of chances to get it right. We also had skills, dedication, and 15 months to research, interview, write, and edit.

 

I had an amazing coauthor who I loved working with. We improved each other’s writing throughout the whole process.

But you know what did feel like a risk? Promoting the book.

 

Sure, I was happy to show up and give talks; that’s just part of the process. But the act of putting work out there to try to get attention for the ideas in Meltdown—I just didn’t do that. For nearly two years!

 

Instead of marketing the book, I waited for people to discover it (fortunately, some did and it resonated with them—something that’s led to interesting professional opportunities). I didn’t write, I didn’t blog, I didn’t try to connect with an audience. That’s what felt scary to me.

What if no one reads my stuff? What if I promote the book and no one likes it? 

 

Walking my path—journaling, therapy, meditation, coaching—helped me understand that fear was limiting me. Since then, I’ve been working with that fear. I try to treat it like a friend who is just trying to keep me safe.

 

I’ve also put together a great team that helps me with the work. It’s hard enough to overcome fear, and even harder when there are lots of other barriers along the road (like having to format emails and set up a mailing list).

 

That’s the journey I’ve been on these past six months. (Thanks for being here with me!)

 

So, back to the podcast: I was talking with my partner about my anxiety and it struck me that one of the things going on here is that I know this podcast isn’t great yet.

 

I’m producing content that doesn’t live up to my own standards. It’s in a medium I haven’t worked in before with an audience that I’m still defining.

 

When I had that realization, everything clicked into place. My fear of not being good enough at this (and, of course, some fear of not being “good enough” to my core) collided with my fear of not being relevant, not being out there in the world. I was holding myself back from doing work that mattered to me.

At that moment, I was able to take some solace from the wisdom of Ira Glass.

 

If you’re not familiar with his work, Glass is one of the most preëminent storytellers in the world. He practically invented the story-based radio genre.

 

Beyond the wildly successful show This American Life, Glass has produced film and TV projects, the popular podcast series Serial. He has also paved the way for amazing creatives like Alex Blumberg, the creator of the podcast StartUp and the CEO of Gimlet Media.

 

Glass is a master storyteller.

 

Ira Glass has this amazing piece of tape where he talks about the creative process. As a creator, he says, you want to create because you love the medium. And that love of the medium means that you have really good taste.

 

But, at the beginning of your journey, there’s what Ira Glass calls a gap:

 

For the first couple of years that you’re making stuff, what you’re making isn’t so good. It’s not that great… it’s trying to be good, it has ambition to be good. But it’s not quite that good….

But your taste, the thing that got you into the game, your taste is still killer. Your taste is good enough that you can tell that what you’re making is kind of a disappointment to you. You can tell that it’s still sort of crappy.

I want to make a podcast because I love podcasts. I love the deep connection that audio allows. I love the medium for what I learn from it and the feelings it evokes in me.

 

And that’s where my anxiety comes from. I know what great work sounds like. I have a belief, an old story, that I should be good at stuff. And I know that I’m not yet very good at this yet.

 

At this moment, I choose to fully inhabit that gap. Not only does my work not measure up to my own standards, I’m releasing it into the world for others to possibly agree with that assessment.

 

That’s not intended to be self-critical or self-effacing. I’m actually doing work that I think is kind of crappy… or, at least, not great.

But the best thing I can do right now is to release mediocre work.

 

As Ira Glass puts it, “The most important possible thing you could do is do a lot of work. Do a huge volume of work.”

 

I know that I’m going to be much better at this in three months. I’ll be even better in six months, nine months. At some point, I’ll recognize that I’ve started doing really good work, maybe even the occasional piece of great work.

 

Until then, I’ll keep growing, keep trying to do better.

Great work is a journey, not a destination. 

 

These are the kind of conversations that I’m going to be having on my podcast. Conversations about what’s hard about growth. Building a business. Walking your own path as an entrepreneur, as a creative, as a leader trying to break new ground.

 

Once I realized that my anxiety sprang from feeling like I had to produce great work and knowing that I wasn’t, I was able to let go of the story that my work “should” be anything at all.

I’m doing a good enough job.

 

I’m excited to get better at podcasting as a medium. And I’m really excited to use my skills to advance the art, in whatever small way I can, of solving complex problems in a way that’s relational and in touch with our humanity.

 

So, without further ado, I’m excited to welcome you to my podcast. It’s no Serial (yet), but we’ve captured some great conversations with people that I truly respect. We’re talking about stuff that matters in this unique moment and I’m excited to share these with you. For me, it’s also a great exercise in showing my vulnerability and learning by doing. I’m looking forward to learning with you by my side.

 

Thank you for being part of this journey with me.

 

Let me know what you think. I look forward to hearing from you.

 

Listen to The Breakdown™ with Chris Clearfield here:

 

Subscribe here to get these articles in your inbox (and to get a free sample from my book, Meltdown).

Now every gambler knows

The secret to survivin’

Is knowin’ what to throw away

And knowin’ what to keep.

 

-“The Gambler” by Kenny Rogers

 

Q3 of this year turned out to be a lot.

 

Sometimes I felt overwhelmed (OK, a lot of the time, as regular readers will know). Work, parenting, moving, a pandemic—it adds up!

 

At work, my team and I tackled projects that felt meaty and satisfying.

 

I lead some big and interesting enterprise consulting engagements. I strengthened relationships with my coaching clients and invested in professional development to deepen my craft.

 

Our team experimented with using paid traffic to explore a few different approaches to marketing my coaching work, which my executive assistant Rahne initiated and drove via our Objective and Key Results (OKR) process. This effort allowed us to test different niches.

 

We are also launching a podcast and wrestling with our process there to make it manageable.

 

One of the things that we noticed was that we had too many Q3 priorities.

 

It showed up in many ways, but something I noticed was that one of our Objectives was different from the others.

 

Said objective was to explore the idea of an online fulfillment-based bookshop for authors.

 

The basic idea was that authors send out a lot of books. It’s nice to sign them for friends, colleagues, and business contacts. It’s also a huge hassle.

 

But what if we authors could sign a BUNCH of books at once, send them to a fulfillment service, and then drip them out as needed with a few clicks instead of heading to the post office?

 

We tried to see if others might be interested in this idea, too. We created a landing page to gather email addresses, and we ran a few ads and experiments.

 

While we had some interest, two things became quickly clear to me:

• We had a lot going on.

• My energy was pulling me toward other things.

 

Every time I was supposed to do something to advance the signed-bookshop idea, I found myself avoiding it. I felt guilty.

 

Then I realized that I was being silly. I was avoiding it for a good reason, actually: it wasn’t in our core set of competencies.

 

It was an interesting experiment, but it took up more time and effort than I hoped.

 

So, I got together with my team to discuss what we wanted to do.

 

We ultimately ended the experiment, and I learned a lot about how to gracefully kill a project.

 

Here’s what I learned, in three easily digestible steps:

 

1. Follow the energy.

 

Tune in to where your energy is actually going; procrastination often serves us in some way. In this instance, it was telling me that my energy directed toward other things.

 

Even Netflix binges might mean that there’s a mismatch between your stated goals and your hidden commitments.

 

2. Ask your colleagues what they think.

 

Most of us don’t operate in a vacuum, which would be very loud (or very quiet depending on the kind of vacuum).

 

So, seek input from your colleagues. They might see something that you miss—a compelling reason to continue the project or another reason to halt. And the participation, if done sincerely, is empowering, hopefully even to the people who ran the project that you’re thinking of ending.

 

3. Celebrate the end of your project.

 

We celebrated the end of our project. With a bit more planning, we could have given it a jolly good sendoff.

 

 

Instead, our fully remote team had to settle for a champagne gif in Slack.

 

The important thing was that we acknowledged that we weren’t going to pursue our Objective. We hadn’t failed—like nearly every project, it had been an experiment!

 

I took a moment to especially thank my marketing specialist Gabe, who had taken point on this Objective, and then we moved on.

 

Final reflections

 

One of the cornerstones of the OKR process is flexibility. As long as you’re thoughtful, you can add and drop Objectives as your situation changes.

 

I love that the OKR process gave us the power to see how some of our work didn’t quite fit in. And I love how it allowed us to drop something in order to move forward with what was working—without any shame or stigma.

 

My only regret is that we didn’t plan ahead a bit more to have actual chocolate or wine to celebrate.

 

Have you killed projects at work? How did you do it and what did you learn?

How science can help you figure it out

 

How do I know what the next right thing to do is in my business?

 

That not knowing—it’s an anxiety that many of us feel, particularly those of us who run our own businesses.

 

In my work as a business consultant and coach, I am asked variations of this question—what’s the next right thing?—all the time:

 

“How should I empower my team to make better decisions?”

 

“What should I do to grow my legal practice?”

 

“How do I work with the kind of clients that I want to?”

 

These are useful questions, but sometimes they can lead consultants, coaches, and mentors to what writer Michael Bungay Stanier calls the “Advice Trap” (also the name of his new book).

 

This is particularly true if such questions are paired with the frequent companion question, “How have other people solved this problem?”

 

The answer is: it doesn’t really matter.

 

Sure, it’s good to look around and see what other people are doing.

 

But other people… well, they’re not you!

 

The things that brought them to their problem are different than what brought you to the problem (even if it looks the same). Your superpowers are different than theirs; so are your challenges.

 

So, what to do?

Run experiments.

 

I was recently working with a lawyer who was trying to figure out where to place her marketing focus. She already has a niche and a successful practice, but she wants to attract more of the right kinds of clients.

 

What should she focus on? Video? Facebook ads? Blog posts? A newsletter?

 

The answer is: no one knows.

 

Sure, there are experts in each of these fields who would provide their own points of view.

 

But the real answer is: try, measure, and reflect.

 

When I was an undergrad working in a biochemistry lab, my professor used to say that his favorite experiment was one that yielded insight regardless of the outcome.

 

To do that in the business world, you have to have a bit of a system. You have to try something for long enough to know whether or not it’s working.

 

You have to choose a strategy and change a small part of your approach as you go along—the text of an ad, for example—rather than jumping between strategies before you’ve gathered enough data to tell whether something is working or not.

 

It’s not limited to marketing, either. You can develop experiments to evaluate a product before you launch it, to expand your business, or even to focus your practice around a specific niche.

 

I’ll share more about my own tests next week, but, in the meantime, I’m curious: what do you want to test next?

 

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It’s funny how the internet can give me shots of anxiety as I casually brush against it in my everyday life.

 

Sometimes these shots come from sources I’ve actively sought out, like the latest news. But anxiety can pop out from unexpected places, too.

 

A tweet, email, or message I read in what could be a moment of rest will instead stir up thoughts and fears, often in the form of old programs that run in my brain (what coach Jerry Colonna calls “ghosts in the machine”).

 

For me, “anxiety as a service” is one of the unintended consequences of the always-on technology of our lives.

 

This happened a few weeks back. I wrote an article about car troubles, asking whether my alternator failure was caused by parking under high-voltage power lines (my conclusion: I don’t think we’ll ever know).

 

As an experiment, I posted the question on Quora, and one poster (helpfully?) latched onto the cost I paid to have the alternator replaced: “I still think that you were taken advantage of at seven hundred bucks.”

 

Amidst the discussion of induced current and transient voltages, that comment triggered a reaction in me. It set off a long-standing part of me that fears being taken advantage of — a program that has probably been in my family for generations. Even now, writing, I feel a tightness in my chest (“What if it’s true? Everyone will take advantage of you! You’ll lose everything you’ve worked for and descend into total collapse [destitution, shame, judgement, failure, etc., etc., etc., etc.!!!]!”).

 

Phew.

 

The good news, though, is that in noticing my reaction I can start to work with it. This includes accepting that the fear of being taken advantage of will always be a part of me.

 

And that’s OK! It’s just trying to do its job of keeping me safe (and, empirically, it has kept my dad and those before me safe).

 

But I also want to stay in the driver’s seat. And I know that if I push this part of me away it will, paradoxically, get stronger and more insistent.

 

So, I sit with it. I don’t need it to go away, I just need to work with it skillfully.

 

Part of how I do that is by working with others. Coaching and facilitating — deeply relational work — both highlight these issues in a way that just sitting and thinking doesn’t.

 

I also share these stories with my team, my friends, and my readers.

 

I talk about them with a coach. I journal.

 

Combined, these practices help me develop the skill of reflective curiosity, which, in turn, helps me notice when one of the parts of me has gotten activated. It’s a beneficial cycle, an internal flywheel.

 

I’ll never be done with this work. But every moment of reflection helps me be conscious of what I’m reacting to in my life.

 

That awareness lets me move toward fear, lets me say “I don’t know, but let’s try this out,” and lets me be vulnerable because I know that I’ll be OK.

 

For example, I did something scary this week. I facilitated a diverse group of lawyers from different organizations who had come together to try and solve a very complex problem. It was, of course, all online and we used a variety of tools to collaborate.

 

I was open about my fear. “I don’t know if this is going to work. This could be really embarrassing. I’m taking a personal risk here.”

 

But I knew that it was going to be OK. How?

 

When you get down to it, I was sitting comfortably in my home office. I was fundamentally OK. My fear wasn’t about what was happening in that moment, it was about what has happened in the past. If I messed up, I wasn’t going to be excommunicated from the group and starve to death in the desert. I was just going to be a little embarrassed.

 

In my view, moving toward fear is the core skill needed to thrive in our modern world.

 

That’s because the modern world is one that’s largely devoid of answers. It is so complex, so interactive, that no one — neither experts nor leaders — knows “what to do.”

 

That doesn’t mean that there aren’t solutions. But solutions come from experimentation. They’re not known, they’re discovered. And that discovery starts by embracing the not knowing, discomfort and all.

 

Subscribe here to get these articles in your inbox (and to get a free sample from my book, Meltdown).

Here’s what you should do instead

 

Does your team feel empowered to speak up at work?

 

Are you sure?

 

One of the most exciting lines of research that we wrote about in Meltdown was what academics call “implicit voice theories”: people’s unspoken beliefs about when it is OK to speak up at work.

 

Researchers Amy Edmondson, Jim Detert, and others have looked at how people form theories about when it is safe to speak up (and when sharing something could be risky).

 

It can be a depressing picture. Many leaders don’t actually listen and doing so can lead to lots of bad outcomes for businesses, from inefficiencies to outright… meltdowns (to borrow a phrase).

 

To see how this works in practice, imagine a well-meaning business owner named Jonathan.

 

Jonathan has owned a construction engineering firm for about 12 years, and things are going well. The firm has recently grown to 33 people, and he finally feels like he has professionals in his leadership team that really know the business. Six months ago, he made a great hire in Karthik, his new director of operations.

 

Jonathan loves the engineering work, but he also loves learning about leadership and management. He’s part of a few professional networking organizations, regularly attends talks, and reads lots of management books (Good to Great is his favorite. He’s got a copy of Meltdown on his shelf, but he hasn’t read it yet…).

 

Jonathan talks a lot about his willingness to receive input, using phrases like “You all know that my door is always open.”

 

But, when team members share concerns with him, Jonathan’s response doesn’t always match that stated openness.

 

Take this example: Karthik sets up a quick Zoom to discuss a complex, cross-functional project (aren’t they all) between his group and the sales team.

 

Karthik: I don’t think we’re going about this project the right way. It’s becoming clear to me that the sales folks don’t know what they want; they’re asking us for numbers that don’t make sense to me.

 

Jonathan: Well, that’s what we decided. It would be too much of a hassle to change now, so let’s just go with it.

 

Karthik: OK, but it will be a lot of work and I don’t think that we’ll get the results we want.

 

Jonathan: That’s just the way it is. We can revisit this in October, after we’ve done our part of the work.

 

Do you see what happens here? Karthik raises a concern. Jonathan doesn’t argue with Karthik, punish him, or yell at him; he just dismisses his concern.

 

Ignored suggestions can poison a culture. Karthik now understands that his input isn’t really wanted, open-door policy or not.

 

So, what can we do as leaders to get better input? I’ll draw on three recent instances from my team as examples.

 

1. Publicly highlight the benefits of input

 

My executive assistant recently shared an observation about how other successful coaches she’s worked with generate business. Because she’s done a lot of freelance and marketing work, she’s seen the inside of lots of businesses. That gives her insight on what works in other places.

 

In a recent team meeting, I highlighted how valuable her observation was, described why it helped me, and asked her and the team to share more.

 

2. Speak last and act on input

 

My marketing strategist, Gabe, recently suggested that we delay the launch of our podcast, The Breakdown.

 

We had originally intended to have three episodes ready to drop right away, followed by a weekly drip. But, because of some production delays (and my commitments elsewhere), we were a bit behind schedule. I thought it would be OK to move forward with only one initial episode in our feed, something I mentioned in passing.

 

But Gabe pushed back. In a recent meeting, he talked about the research that he had done and described the benefits of launching with a block of episodes.

 

I solicited input from everybody on the team. We discussed the advantages of delaying and any complexities that it might cause. We then took a minute to come to a “launch/delay” decision independently. After our discussion, everyone, including me, thought that we should delay.

 

It would have been easy for me to double down and push forward—after all, it was our goal to launch this week. But there was actually no upside to that, and it made much more sense to listen.

 

3. Understand your own triggers (and give your team a map to navigate them)

 

After our conversation about delaying the launch of the podcast, I reiterated how valuable I find my team’s input.

 

And I also shared a specific way for them to get my attention, one that I drew from my experience as a pilot and immersion in flight safety literature.

 

When I get stressed, I drive more. I push forward, digging in and getting a bit stubborn. I can shift from a stance of curiosity to a desire to argue that I am right.

 

But I taught my team a secret power, a specific way of engaging with me to remind me to slow down:

 

“Hey Chris, this is important. I’d like you to take some time to think about this before we move forward.”

 

It’s the same way pilots are trained to get each other’s attention. It’s a cue that tells me that I’m moving too fast and need to tune in.

 

And it’s one of the ways that I’m trying to gather more input from the people who understand many of the challenges and opportunities in my business better than I do.

 

One final note to close. The idea of an implicit theory of when people can speak up is a twin to the concept of psychological safety: the willingness of teams to experiment and share beliefs, even uncomfortable ones. Amy Edmondson pioneered the ideas around and measurements of psych safety, as we call it “in the biz,” and has written about it for decades, most recently in her fabulous book The Fearless Organization.

 

What about you? What strategies do you use to get your team to share with you?

 

Subscribe here and let’s keep the conversation going.

I often get overwhelmed in the evening.

 

I’ll reflect on my workday and look at the list of all the things I didn’t accomplish, the calls I didn’t make, the emails I didn’t return (the newsletter posts that I haven’t written yet…).

 

I wrote about this last week: the ways overwhelm holds me back (and the strategies I use to work with it).

 

Overwhelm is a common problem for the entrepreneurs that I work with, often because they try to do everything themselves. Although that may work for a while, it is ultimately unsustainable.

 

Instead of doing everything themselves (and getting overwhelmed and burned-out in the process), entrepreneurs should consider scaling the system.

 

Here’s one definition of scale.

 

scale, verb: to quickly grow a business to unsustainable levels, often while losing lots of money. Principally used in Silicon Valley.

 

Of course, this definition is cheeky — but not too cheeky. Some major challenges in technology (hate speech and fake news on platforms like Facebook and YouTube, for instance) can be traced to unconstrained growth without adequate systems to support it.

 

But, as someone who runs a small-but-impactful business, I’m interested in a more practical definition of scale.

 

And so are my coaching clients, who are more likely to run medium-sized firms than they are to lead big tech companies.

 

For me, scale has a very simple definition: work gets done without me being involved.

 

Passive income from things like book royalties or the sale of online courses is a form of scale. Profit happens without people doing anything.

 

But even businesses that don’t generate passive income can scale. Here are three strategies that I help my coaching clients use.

 

Create systems and automation

 

Automate what can be easily automated. For dollars a month, you can use tools like Zapier to add customers to your CRM, add payments to QuickBooks, and just generally make your life better.

 

But automation is a double-edged sword.

 

I’ll be the first to admit that I sometimes suffer from “automation fever,” whereby I spend an inordinate amount of time building complex automations for trivial tasks.

 

There are two cures (three, if you consider the placebo effect of more cowbell):

 

1. Develop clear criteria for when a task should be automated. Before you decided to automate something, understand how much cost a manual task actually takes. Is time the principal issue? Inaccuracy? Opportunity cost? Or does manually doing a task interrupt your creative flow?

2. Automate parts of a task. My executive assistant manages my calendar, but I also have a scheduling link that I send to people who are more likely to self-schedule than to respond to an email from her. The hybrid solution is better than being entirely automated or entirely people driven.

3. Remember that systems and automation don’t have to involve technology. For example, batching content creation is a powerful way to get more done in less time (incidentally, shifting to batching will be part of our work next quarter).

 

Hire great people and let them make mistakes

 

The next aspect of scale is hiring great people and letting them do great work. Plenty of business owners I know hire people and then proceed to micromanage them.

 

So much of micromanaging is about fear: fear that a detail will be missed, fear that the task won’t be done as well as you would do it (although “as well” often translates to “the exact same way”).

 

Let me let you in on a secret: the people you hire will make mistakes.

 

But that’s OK!

 

Don’t forget that you make mistakes, too. And, for 99% of tasks, mistakes are not catastrophic (or even particularly impactful).

 

The best people you hire will be better than you at their jobs. They’ll know marketing better than you. They’ll be more organized or more detail oriented than you. And, if you do it right, they’ll actually be less likely to make mistakes than you.

 

Part of the reason why hiring a good team is so effective is because it allows a leader to focus elsewhere. Your goal is to home in on your area of greatest impact: connecting with clients and delivering outstanding value to them.

 

Make sure you have a clear, actionable vision so people know what their best work is.

 

What’s better than hiring someone to support you in your job? I would argue that it’s hiring a team that works well together.

 

This doesn’t happen by accident. Sure, you need to hire people who aren’t jerks.

 

But you also need to define a clear, actionable vision. There are lots of ways to do this; last week I mentioned using the Objectives and Key Results approach (website, book) to define your strategy and let the appropriate supporting actions emerge.

 

When this is done in a collaborative way, you will have achieved something that few businesses do: distributing ownership. People will define what they are going to do, sometimes in areas that break new ground for your business, and they will do it better than you — all without your involvement.

 

In my business, we have a positive example of this. This quarter, my executive assistant, who I mentioned above, saw an opportunity to use paid traffic to promote my coaching business (to date, I’ve grown it through organic networking and relationships).

 

She’s done a fantastic job creating an entirely new way for us to engage with potential customers, all because we had the clear objective of expanding the coaching business and she had the skills to work with an outside partner to develop and execute our strategy.

 

That’s the true path to scale.

 

Before I end, I want to ask you something: did this article overwhelm you? I know that yet another article about what to do better can be really tough.

 

If so, not to worry. Remember: you are enough and you are doing enough right now.

 

The work of scaling isn’t just about systems, people, or an actionable vision. It’s about realizing where your own overwhelm sits, where your own fears sit, and learning to work with them skillfully.

 

Subscribe here and let’s keep the conversation going.

Why do I feel so overwhelmed?

 

Last week, I wrote about fear, how I sit with it, and the effect that it has on many of us.

 

This week I was going to switch gears and write about something a bit more tactical, about what it means to scale a business — not in the Silicon Valley sense of “Get a gajillion users” but in the sense of “Run your business more effectively with less involvement and stress.”

 

But, as I dug into that, I realized that many of the barriers to scale come back to one thing:

 

Overwhelm.

 

So many of the business owners who connect with me for coaching struggle with feeling overwhelmed. There’s probably an element of selection bias in that. But I think there’s also an element of universality.

 

I struggle with feeling overwhelmed, too.

 

For me, it often comes late in the day. I usually wake up excited to dive into work. I’ll work on what I need to, and I’ll get things done, have calls, move projects forward, and connect with my team.

 

But, if I don’t get everything done (which is basically everyday!), I often will start to feel anxious and overwhelmed.

 

Why?

 

For me, I think there are a couple of underlying reasons.

 

I’m a very “left brain” guy. My analytical ability and my capability to tease things apart is one of my superpowers, but the left brain also keeps track of all the unfinished things. In moments of overwhelm, it’s hard for me to zoom out and rest in the work I’ve accomplished that day. My survival instinct parses the world apart, looking for the threats and focusing on what’s not done.

 

There’s also a component of self-imposed upper limiting behavior here (in other words, I get in my own way because I have a hidden commitment that is holding me back). I’m a big fan of the work of Gay Hendricks (The Big Leap, among many other titles) for his perspective on how we can move beyond our limits. Even as I move toward achieving my goals through the work that I love, I hold myself back.

 

One thing I’ve learned is that overwhelm isn’t something that I can outthink. Working with it skillfully involves working with three different aspects: mind, hands, and heart.

 

Mind is the aspect that we’re perhaps most familiar with. Strategies like writing tasks down to get them out of our working memory is a prerequisite (the cornerstone of systems like David Allen’s Getting Things Done). SMART goals can help us organize our work (see this great Khan Academy video made for elementary school kids for some helpful tips). And my team and I use quarterly Objectives and Key Results (website, book) to focus on what’s important.

 

There’s another aspect of organizing the mind that helps, too: limiting work in progress (WIP). An excess of WIP means that people are constantly switching between tasks. Instead of starting three tasks and spreading them out over three weeks, start one and bring it to completion before you move on to the next. My team and I have been chatting about limiting WIP this week; it’s a version of the laundry basket problem that I’ve written about before.

 

Hand is the doing. Ironically, the most effective way to avoid overwhelm is by not doing something.

 

What are you able to let go of and still get things done? This involves setting up systems and hiring great people. It requires empowering your team by setting goals, allowing mistakes, and avoiding micromanaging. It also involves developing a clear strategy (whether you’re the CEO of a multimillion dollar firm or a new graduate who’s just starting out), so you internalize the cost of saying yes and recognize what to say no to.

 

Finally, the heart. By heart, I mean not only feelings but the fundamental complex core of the matter. For me and many people I work with, overwhelm is a felt experience. It shows up in the body. To work with it, we need to meet it in the body.

 

We need to feel what’s happening and tune into our sensations. This is hard work, particularly for those of us who have built our success on the practice of deep, analytical thinking. In the past few years, I’ve gotten a lot better at recognizing feelings as they arise — but it’s still difficult to stay with them.

 

But, like sitting with fear, it’s a skill we can develop. Different things work for different people.

 

When I run without the distraction of a podcast, audiobook, or music, I’m more likely to remember to settle into my body. Even a relaxing shower helps.

 

Or I can consciously shift my perspective, bringing my visual attention to the whole scene around me instead of building my awareness from the specific features around me. My theory is that this technique shifts me to the right hemisphere of my brain, which is much less bothered by my to-do list because it holds the broader arc of my work.

 

Finally, I also work with a coach, who uses curiosity to help me stay with my sensations, and with a skilled massage therapist, who engages my body and holds space for my feelings to move me out of my thinking mind. This kind of work can be transformative.

 

How do you work with your overwhelm?

 

Subscribe here and let’s keep the conversation going.

I recently started offering a limited number of free introductory coaching calls to people who are interested in learning more about business coaching and what it might be like for us to work together.

 

Many of these folks are successful business owners who want to grow their companies but feel like they can barely keep up with the volume and complexity of work they have right now.

 

Others are professionals, like lawyers, who see their industry changing and want to figure out how to build a practice that will remain relevant for years to come.

 

But I also talk with new business owners, some of whom have lost their jobs amidst the COVID-19 pandemic and have had to make drastic shifts in their lives and in how they see their place in the world.

 

I recently had a call with a prospective client who was struggling to get her new accounting business off the ground. While we won’t end up working together long-term, our conversation brought me a deep feeling of connection.

 

Some of her challenges were unique to her situation and her practice. But a lot of what we discussed was fear — something I’m familiar with.

 

Fear that she wasn’t good enough.

 

Fear that she couldn’t do it.

 

Fear that she was foolish for trying to follow her own course.

 

One way she experienced fear was as a voice in her head. She likened the fear voice to an “ex who doesn’t want you to feel good enough on your own.”

 

“But I know I can do it,” she told me. “I know that if I can push through my fear, I can start my business and be successful.”

 

I paused. Her comment really hit me.

 

I took a moment to connect with my own fear, and I realized how present it is for me.

 

I also realized that I’ve learned that I don’t need to push through my fear, as she suggested. I don’t need to force it away.

 

I’m still able to move forward — not because I’ve gotten rid of my fear, but because I’ve made friends with it.

 

Here is a sampling of my fears:

 

I’m afraid that I won’t make enough money and that I won’t be able to balance my roles as a leader, a father, a romantic partner.

 

I’m afraid that I won’t be as effective with clients as I want to be, that I won’t be useful, and that I won’t be asked back to do more work.

 

I’m afraid that I won’t have an impact on the world, that my ideas won’t help make things better.

 

Ironically, I’m also afraid that I’ll stand out and that not fitting in will lead to rejection.

 

Your fears are probably different from mine; our fears are our own. But I suspect that there is something nearly universal about fear itself.

 

Fear is uncomfortable and hard to sit with. Our instincts are to stay safe by moving away from it.

 

And therein lies the rub: even when we ignore fear, it’s still there. All we’ve done is put it in the driver’s seat.

 

Fear is crafty; it can alter our behavior, making us change our plans or lower our ambitions without us even noticing that we’ve limited ourselves. It can make us shy away from risks and avoid activities — like business development or *gasp* writing — that we know will help us widen our reach.

 

After my book Meltdown was published, I was reluctant to write things on a regular basis (such as, say, this newsletter!). I did write op-eds and think pieces, but I wasn’t writing about what, deep down, I knew I wanted to write about.

 

I was trapped in a fear loop. On the one hand, I was afraid of the judgmental part of me that decried “imperfect” work. On the other hand, I was afraid that I was becoming irrelevant; not writing gave ammunition to that judgmental part.

 

I was stuck.

 

But no more.

 

Often the things we fear are precisely the things that we need to do to move toward. I was afraid of writing. That’s because it was exactly what I needed to be doing, exactly how I needed to be engaging with the world.

 

Or take the example of my fabulous newsletter editor. She recently told me that she’s procrastinated for years on setting up her website. She’s afraid — of getting it wrong, of having to learn new technology, of being out there. But she also realized that her fear is a guidepost to how she wants to move forward — and it’s now part of her objectives this quarter.

 

And this is what I invited my client to see: it’s not about overcoming fear or using willpower to make ourselves do something that we don’t want to do. It’s about listening to and respecting our fear, knowing that it wants to keep us safe… when what we really need to do to grow is take a risk.

 

Whether it’s searching for a job that will meet a deep need that we have, starting a business, or working with a therapist or coach to walk the path of growth and discovery, you don’t have to overcome your fear, you just can’t run from it.

 

The good news is that sitting with fear is a skill, one that you can develop by yourself, with your colleagues, with a friend or romantic partner, or with the help of someone like a therapist or a coach. Developing the ability to sit with fear can dramatically alter your trajectory in life — I have seen firsthand how it opens up areas of prosperity, success, and health, and how it deepens relationships beyond what I’d ever imagined.

 

What about you? Are you ready to sit with your fear?

 

*Click here to learn more about booking a free coaching session.