Every leader I work with has a routine (conscious or unconscious), and the results that they get are directly related to the habits that they have established.

I want to share a few things that have worked for me, with the hopes that if you make even one change in your existing routine, it can have a massive impact on your results.

It All Starts with Your Physiology

If you are running around in a panic, you are not going to create good results.

So the question I like to start with is—who do you want to be?

When they get past the goals, financial, business, and otherwise, most people I talk to say things like—

— I want to be a person who sets and achieves goals with ease.

— I want to be more calm and present.

— I want to make better decisions.

— I want to have better relationships.

— I want to be more creative and engaged in the work that I am doing.

— I want to live a life of minimal regret.

All of these start with your physiology.

You can’t do any of these when you are consistently in fight or flight. So having a routine that minimizes the time you are in that state will pay exponential benefits.

It Must be Doable

I work with a lot of overachieving leaders. And when the topic of a morning routine or habits comes up, they often try to design the perfect routine—I’m going to meditate an hour a day, I’m going to do yoga, go to the gym, train for an ultra, etc., etc.

And like the New Year’s resolution that lasts two weeks, this approach fails over and over.

Start Small and Build

I once asked a leader to set aside one minute a day to breathe deeply. Because we had done that in a session and he had felt the impact in just that one minute.

If you get success with small things, it will reinforce itself and you will take on more. A virtuous cycle that will pay increasing dividends over time.

A Sustainable Routine that Works for Me

Here are the things that I have been able to implement and sustain over time. And a couple things that I am trying to get better at incorporating.

Meditation

I used to meditate an hour a day. For years. But it stopped working for my schedule once I started my own business. I went months without meditating at all and I noticed my reactivity was increasing in its absence.

In the past few months I started a new habit. After I make my coffee, I meditate for five minutes. That’s it. And my focus is on belly breathing, the 4×4 exercise (four seconds inhale into the belly, exhaling out my stress and thoughts, repeated four or more times) that I recently wrote about. It clears my head for whatever is coming in my day.

Journaling

After I meditate, I pull out my notebook and write for three pages, an exercise called “Artist’s Pages” first written about by Julia Cameron. But I ask specific questions—What is being called to be created by me today? What is it that my higher self wants me to know about myself today? Who do I want to create myself as today?

Once the ink starts flowing (I highly recommend that you physically write rather than keyboard), something opens up and I almost always see something about myself or the world that I did not see before. And that reinforces my understanding that each of us is literally creating ourselves fresh and new in each and every moment. There are limitless possibilities, if only we get in the habit if seeing them!

Exercise

My wife routinely goes on ten mile hikes. I confess I am much more utilitarian in my exercise, focusing on what is the minimum dose of what I need to feel the way I want to feel.

For me, that means resistance training and aerobic training. I am trying to incorporate more work around flexibility, such as through yoga, as well, but it is not as established as I would like it to be.

For resistance training, it means a simple weight working on machines and with dumbbells, exercises done to failure. I often incorporate what are called “drop sets,” which means you do a set to failure, drop the weight significantly, then do another few reps to failure again. it is intense but it works. I feel great after a workout. I can get though my weight workout in about 20 minutes and I do it twice a week.

For aerobic training it depends on time of year. I try to have it be outside—a run with the dog for 30 minutes to an hour, or cross country skiing, or carrying a weighted backpack uphill. I try to do sprints or short intervals (100, 200, or 400 meters) once a week or so for variety. Sometimes I end up doing those intervals in a treadmill but it is not my preferred approach. I do two aerobic workouts a week.

Time Outside

There is lot of research pointing to the fact that time outside helps us with both stress and creativity.

I walk outside with the dog two or three times a week for about an hour (I share dog duty with my wife—the dog gets out every day!). It can be difficult to get out sometimes, especially in the middle of the day, but I’ve found it’s a good time to listen a podcast or make phone calls, so it can serve double duty if needed. I also find that a hour walk while doing absolutely nothing else can be incredibly energizing and head clearing when I feel like there is just too much going on.

Having A Hobby

My newest addition to this routine is playing the saxophone. I first picked up a saxophone on April 6, 2023 (I sang growing up but have never played an instrument) and it has become the part of the day that I consistently look forward to the most. What I love most about it is the fact that I have to be present to have any chance of doing it well. If I have anything else on my mind, the horn lets me know, immediately.

Building YOUR Routine

Those are the elements of my current routine, and they have been cultivated over a period of years. They also change from time to time based on what else is going on in my life.

But every ingredient brings me some combination of joy and building my capacity to be calm and present with whatever else is going on in your life.

What are the elements of your routine? I’d love to hear what works best for you.

I’ve been in conversation with several founders about fundraising in the past few weeks. Each is in the process of raising, or has just completed raising, millions of dollars.

Each founder brings a different pitch to each conversation. But they also come from a different place.

And I notice that the place the founder comes from has a bigger impact on their success than the product, the industry, or the pitch.

Let me start with two examples—

Founder A is in the process of raising $25 million for his company. I ask him how it’s going.

“I’m so stressed. My calendar is not my own. I’m chasing people trying to do anything to get a meeting and then when I do get one, it ends up a waste of my time. And then I run to the next conversation, knowing that if I don’t find some money, fast, I’m not going to meet payroll. I know it’s a numbers game, but it’s so hard to keep going.”

Founder B is in the process of raising a similar amount. I ask her the same question—

“I’m feeling pretty good. We are having conversations with a few good potential partners. But we do a really good job of screening them before we get into a serious conversation so the time away from my team and doing my other work on the business is pretty minimal. We’re not there yet, but I’ve a feeling we’ll end up with someone we feel really good about.”

Two founders, two very different experiences. Why the difference?

What Else are You Bringing to your Conversations?

Fundraising can feel like an existential crisis—

It’s about the quality of my idea.

The quality of my pitch deck and my projections.

My experience. My team. How well I tell my story.

My performance.

My very sense of self-worth can feel at stake.

And everyone knows that cash is the very lifeblood of a business. If I run out, the business dies, along with my dreams of finally proving myself.

Exaggeration? Maybe a little. But does it resonate?

If it does, can you understand that when you put your very physical and psychological existence on the line, the conversation can feel just a little bit stressful?

What if there was a different, easier way?

Who’s Auditioning Whom?

Most founders I talk with think that the people with the money have the power.

Like actors auditioning for a part, they put themselves in a room with fifty other people, all more experienced and better-looking. And they try to psych themselves up to show up exactly how they think the casting director, the one with the money, is going to want them to show up.

Maybe this time they can be good enough!

But what if you’re actually the casting director? And people are lining up to see if they can please, please, please invest their money with you.

The Big Secrets

There is plenty of money. In fact, there is way more investible money than there are good ideas.

And no one really agrees on what is a good idea—only about one in ten are really going to hit no matter what.

No matter what someone tells you, they have no idea if your idea is one of the winners.

So how do they decide?

Your story. How you talk about your idea matters. Make sure it is abundantly clear why it is different, and how it wins (a big TAM—Total Addressable Market is also nice, but not absolutely necessary).

Your experience. While you can’t change this in any meaningful way, you can change how you talk about it. For example, one of my clients had no meaningful startup experience. But what he was building was actually more about starting at a scale that most founders wouldn’t dream of. And he did have that experience running large organizations. He had the experience that most mattered, even if at first it didn’t look like it.

Your confidence. If you come from a place of auditioning them, of being absolutely clear what your ideal partner looks like and what you are looking for, you will instantly become more attractive as a potential investment.

How to Be Less Desperate (Even When You Feel Desperate)

I get it.

All this sounds nice when you have a year of cash in the bank.

But what if you actually need the money, and soon?

Do your customers care if you can’t make payroll?

Your potential investors don’t either, unless they are using it to take advantage of you. (Not the investors you want.)

You still need to come from an audition mindset. You still need to find the right partner, not just any blank check, because this is the phase where the wrong partner could have a huge impact.

You still need to be one hundred percent confident. Even if you don’t know exactly how things are going to work out, you have to be confident in your ability to figure something out. In your own ability to get out of a jam, just like you have so many times before.

If you feel hesitation, breathe. Deeply. Into your belly. Slowly.

Every time you exhale, let some of that stress you are feeling out. Will it change your situation? No. But it WILL change your body’s experience of your situation, and your potential investment partners will feel that.

Your certainty becomes their certainty. Not cockiness. Not bravado. Just calm, centered confidence.

You’ve got this.

At a Crossroads?

Taking some time away, with a guide who has been there before, might be the best way to get some clarity on what’s next.

I have a couple of ways of doing that. Two days for thinking bigger thoughts. One on one or in a group.

Reach out for more details. Your transformation as a leader awaits.

I just got back from two-and-a-half days with one of my founder clients. Since he bought out his co-founders three years ago, he has grown the company by over five times, and is comfortably in eight figures of revenue.

Even so, he could see that he was holding himself back, but he couldn’t yet see HOW he was holding himself back.

But in our time together, he saw that, and more.

How Does A Retreat Help?

When someone gets out of their day to day environment, several really helpful things happen—

They stop being in reactive, firefighter mode. When you’re in a pattern, it’s really hard to see outside of that pattern.

Their thoughts begin to slow. Their breathing moves into their bellies. Their shoulders drop. Their speaking calms and deepens.

Now, the real work can actually begin.

The Difference Between a Platitude and an Insight

A platitude and an insight can look very similar. But they FEEL very different.

I often run into people who talk about how they are too hard on themselves, or how they are perfectionists, or workaholics.

On some level, they know, at least intellectually, that there is a cost to these strategies. And they are willing to say the “right” things. They know they shouldn’t be doing these things.

But at the same time, they are afraid to let them go.

Why? Because it looks like these strategies have more upside than downside. And they don’t know what else to do.

Until the actual insight comes, the outer behavior will not change.

“I Don’t Want to Lose My Edge”

Most successful people push themselves to achieve. Either by being really hard on themselves, or using others’ perceived slights.

For example, my client says one of the things that motivates him most is to be told he can’t do something. He immediately wants to prove that person wrong.

There are two problems with this kind of motivation—

First, it works! Look at all the sports stars who have used perceived slights as a way to motivate themselves—

Michael Jordon, Kobe Bryant, Tiger Woods, Tom Brady.

All historic greats who used their own anger at others’ insults (sometimes real, sometimes, frankly, made up) as fuel.

Why is that a problem? Because it’s exhausting and unsustainable. It requires you to feel bad to get to a good result. And when you get to that good result, you instinctively find another thing to be dissatisfied with or angry about.

That’s right. You become unable to enjoy your accomplishments.

Enjoyment means complacency means losing your edge means failure.

It’s a cycle that’s very hard to extricate yourself from.

The Two (Contradictory) Insights My Client Had

In a retreat context, we spend a lot of time in silence or near silence. Not because we are meditation, per se, but just because that’s what naturally happens when we give ourselves space.

(Who you are on retreat with matters. I have almost thirty years of mediation experience and am very comfortable with silence. In this context, tools and concepts are not particularly helpful. Your cup is already full. Stop pouring.)

In this space, habitual thoughts become much more apparent.

You begin to get the game you have been playing. And you see it for what it is.

And that’s what happened for my client—

He saw how much of his own internal monologue was self-critical.

And he saw that monologue for what it was. Thoughts that come and go, that have no innate solidity or truth.

Thoughts that, in his case, were not actually not helpful.

He saw another kind of thought as well. Thoughts about having reasonable goals rather than thinking big.

“I’m seeing two things that seem to contradict,” he said to me.

“Tell me.”

“I’m too hard on myself. AND I’m thinking way too small.”

The Power of Both/And

I didn’t TELL my client these things. If I had it would have bounced off him like any other advice. Instead, he saw it on his own.

He FELT it.

By seeing that being hard on himself, which he thought would help him reach his goals, was actually leading him to create smaller goals, he was able to unlock the creative energy that was always there.

And he will take that energy back to the office with him.

I can’t wait to help him create that next version of himself and his company.

What Could You Unlock if I Gave You the Key?

Two days away with your own thoughts and a clear guide is the best way that I know to jumpstart what is possible for you.

There are two ways to do that with me—

First, you can do it one-on-one (with follow up coaching to make sure you integrate it into your return to work).

Second, you can apply for my group event for founders and business owners in Denver on October 20-21.

DM me for details on either or both.

A client of mine recently texted this to me.

It was something he had gotten, intellectually, for years.

But it had never really hit him.

Not only did he not HAVE to know everything.

He can’t. No one can.

But only when he actually REALIZED this could he take action on it.

Only then could he see how free he already was.

Letting Go of Control

Whether they are founders making their next move or successful executives thinking about a job or career change, I see one thing that gets in the way of successful people over and over and over.

It’s the idea that they can figure out how things are going to work out before they actually do anything.

The idea that if they do the right things in the right order it can create a predictable result.

And the idea that they CAN’T act until I have all of that figured out.

Anything involving action in the world is inherently unpredictable.

As much as you try to control things, I can assure you that success comes when you are willing to try stuff knowing that you don’t know what’s going to happen.

Taking action and letting go of your control of the result.

“But how do I do that?” you might ask.

The best way I know of is to see that you never really had any control in the first place.

Creating Through Action

One of my favorite pieces of advice is from coach and teacher Michael Neill.

“Try [stuff]. And if it works, do more of it.”

That’s really all you can ever do.

You can’t learn anything about the outside world when you remain inside your head. You have to take action and see what happens.

What may make perfect sense in your head likely has nothing to do with how things will actually play out.

Ever try to plan a difficult conversation? How long before the other person said something totally unexpected?

And yet, in that moment, you figured out what to do next. Even though it was completely different than what you planned for.

Your Greatest Talent

Your greatest talent is the greatest talent that any human being has—

The innate capacity to figure out things in the moment.

Now I’m not saying that your perspective, your experience, even your planning are not relevant. They are relevant and perhaps even critical. No two people will respond to the same situation in exactly the same way.

But that capacity to respond, in your unique way, is what has brought you this far.

Revel in it. Embrace it. Look for opportunities to use it.

Scary? A bit.

But trying to plan your life without living it doesn’t sound like much of a life at all.