This week, I want to share some lessons I’ve learned from my 15-year-old son, Lucas, as he created his own vision, of becoming an exchange student in Japan.

These insights are especially fresh to me. As I write this, on Monday, he has just arrived after an almost 48-hour journey complete with an unexpected overnight hotel stay in Canada.

Did I mention he’s 15?

Honoring Your Dream

Lucas had a dream—a dream his mom and I didn’t even know about until he told us in November 2023. I had just gotten back from a coaching event in Santa Monica when he announced that he wanted to become an exchange student and go to Japan. While my wife had been an exchange student in Sweden years ago, this was a surprise to us. But Lucas had done his research. When he approached us, he already had the online application process figured out and had talked to his school counselor about the logic of going at 15 rather than when he was older.

I’m not sure that Lucas even knows exactly why he wanted to go—he will say things that food and the culture and manga and anime, but it seems like it is something deeper that is calling him.

Do you see something like this in you?

Honor that dream. There is something within you that you know you want to do. The question is, are you going to honor that? Are you going to trust yourself enough to pursue it? Even if you don’t exactly know how?

One Step at a Time

Lucas didn’t try to tackle everything at once. He focused on one step at a time. First, he submitted the application. Then, he went through an introductory interview, followed by a more significant interview, and finally, a finalist weekend that we attended with him about 90 minutes away.

In each stage, he focused on what was in front of him without worrying too much about the final outcome. He knew he was drawn to this path, and he trusted the process. By the end of January, he learned that he was accepted as an exchange student, as one of the youngest to apply, and that he had gotten his first choice, Japan.

For founders, this teaches us the importance of focusing on the next step and trusting the process. You may not know exactly where the journey will take you, but if you commit to each step, you’ll move closer to your goal.

Accepting Limitations

Another critical lesson Lucas taught me is the importance of accepting limitations. He realized that he couldn’t become fluent in Japanese in just six months, especially before ever being in the country. However, he didn’t let this deter him. He did what he could and acknowledged that there was much more to learn once he arrived in Japan.

As founders, we need to accept our limitations and work within them while still pushing forward. It’s crucial to understand that some things take time, and we can’t control every aspect of our journey.

Navigating the Unexpected

Lucas’s travel to Japan didn’t go as planned. He missed his connection in Vancouver, had to figure out how to spend the night there, and then ended up flying through Korea instead of directly to Japan. Despite these challenges, he kept moving forward, solving each problem as it arose.

For founders, this is perhaps the most powerful lesson: Expect the unexpected. Things will not always go as you expect, but you will figure it out. Keep in motion, adapt, and find solutions to the challenges that come your way.

The Power of a Supportive Team

This was Lucas’s dream, and of course it required support from his parents. But we worried that when he got to Japan, he would be on his own.

Nothing could be further from the truth.

When Lucas arrived in Japan, after nearly 48 hours of travel, he was greeted by his exchange parents, teachers, and Rotary members—a whole team ready to support him in realizing his dream.

Thanks to a supportive teamLucas is going to have an amazing year. And his team is going to learn from supporting him as well.

As founders, we must recognize that we don’t need to be alone. Employees, customers, and eventually investors, board members, advisors, and even coaches are ready to support you.

Each member of Lucas’s team had supported other kids like him and were ready to bring that support to him. Don’t forget that on your journey. There are experienced people ready to support us in realizing our dreams, and the more we can lean on them, the better our chances for success.

Does This Resonate?

Getting support as early as you can will ease and shorten the journey to having a profitable startup.

If you are closer to exit, though, you may be more interested in an event I am having for founders on September 17—

The Other Side of the Exit: Is There Happiness Beyond the Deal?

I’ve recruited an all star panel with dozens of exits among them to answer all your questions about how to get to and thought the exit not only more successfully, but with more ease and less work in the process.

If you’d like to be in a small virtual event with founders just like you, please DM me and we can set up a time to talk to make the event as valuable for you as possible.

#founder #founders #exit

Have you ever found yourself saying, “I’m living the dream,” but you still don’t feel like you’re “there”?

You’re not alone. Many people, especially high achievers, reach a point where they feel they’ve accomplished everything they set out to do. Yet, despite their success, something feels off. They’ve been successful beyond their wildest dreams, but there is still an itch to do more.

They start to feel guilty for or even greedy for wanting more.

This phenomenon is what Gay Hendricks calls the “Upper Limit Problem.” It’s the idea that there’s a level of success that feels uncomfortable because it challenges our deeply ingrained beliefs about how much happiness or success we’re allowed to have.

The Joy of Creation: Beyond Just Achieving Goals

As humans, we are wired to create. The real joy in life doesn’t come from reaching our goals but from the journey of striving toward them. This is why the satisfaction of hitting a milestone often fades after a short while, leaving us wondering, “What’s next?”

When someone says they’ve “got it all,” it’s worth exploring what that actually means to them. Often, people who make this statement quickly start to feel bored, stale, or even guilty. They wonder what they did wrong and why they’re not as happy as they thought they’d be.

And they wonder if they will ever be fulfilled.

The Founder’s Dilemma: After the Big Exit

This sense of letdown is particularly common among founders who have built and sold companies. They’ve sacrificed so much to achieve their goals, only to find that the big payday doesn’t bring the happiness they expected. In fact, it can be hard to repair some of the damage they did along the way, whether to themselves or their relationships.

They might ask themselves, “What’s wrong with me? Why doesn’t this feel as good as I thought it would?”

The answer is simple: There’s nothing wrong with you. The joy and purpose come from the act of creating, not the achievement itself. It’s crucial to remind yourself of this and to surround yourself with others who understand this journey.

You may find that even after the exit you still have this desire to create.

The good news is that now you get to create from joy rather than need. And much of the joy of being a human comes from that act of creating.

Join the Conversation: Creating Meaning Beyond Success

If this resonates with you, I’ve created an event on September 17th called “The Other Side of the Exit: Is There Happiness Beyond the Deal?”

It’s a virtual 90 minute conversation specifically for founders who are within 2-3 years of an exit, with a panel of people who have dozens of exits among them.

This is a chance to get to know other founders like you, and to ask questions to people who have been through it.

If this sounds like you, I invite you to reach out to me. Let’s have a 15-minute conversation about your expectations for your exit. As a thank you, you’ll get to be in the virtual room live as it happens, with a small group of like-minded individuals—other founders who have been where you are, along with panelists who have experienced dozens of exits.

Together, we can ensure that as founders, we are having the right conversations, setting the right expectations, and creating the right things to find true purpose, meaning, and satisfaction in our journeys.

#founder #founders #exit #meaning #purpose

A founder I’ve been in conversation over the last few months sent me an email last week explaining why we hadn’t been able to talk.

“I am so overwhelmed with work I don’t have time to do anything except work. It’s not a good situation but we are slammed and it’s all hands on deck.”

This isn’t an isolated case. Another founder once shared that he makes around 300 decisions a day, with his team relying on him for everything. Many of the people I work with push themselves to exhaustion, neglect relationships, and even develop health issues.

Does that resonate?

It doesn’t have to be that way.

The Cost of Overwhelm

The first step is acknowledging the cost of this constant state of overwhelm. Founders and leaders often find themselves in a vicious cycle of decision-making and fire-fighting, leaving little room for strategic thinking or personal well-being. This not only affects their health but also impacts the overall performance and growth of their organizations.

Change is Possible

Here are few true stories from my coaching experience.

The Sales Leader

About four years ago, I coached a sales leader responsible for a significant portion of sales in a multi-billion dollar organization. She was working 60-70 hour weeks and felt perpetually overwhelmed. Within a few months, she cut her workload by 20 to 30 hours a week. This reduction in hours allowed her to focus on creating her next career move within the organization.

She created a new function in the organization with her as the leader. She happily sits in that role today.

The Founder

A founder I coached in 2023 was able to step back from daily operations, entrusting his team with these responsibilities. This transition enabled him to focus on strategic growth, eventually leading to his company being acquired. Now, he is focused on being the heir apparent to the CEO role of the combined organization. And he has reunited with his wife in the process.

The Company Owner

One company owner I have been talking with, after struggling for years, today has virtually no day-to-day decision-making duties. His team handles operations, and the business is thriving more than he ever imagined. He has achieved both financial success and personal freedom.

I’m now working with him on what he wants to create next. I asked him how he got where he is today and it came down to one simple belief.

The Key Differences

So, what sets these successful transformations apart from those stuck in the overwhelm?

Every one of them was different. But in every case, the leader was able to let go of things that at first looked mandatory.

It was that letting go that led to massive and easy change.

Let’s Talk

Does this resonate?

I’m doing a research project on founders and their expectations around exits—how they will get there and what they will get from them.

If you are a founder within three years of an anticipated exit, respond “Talk,” to set up an interview.

As thanks I will share the results in a virtual event on September 17, in which I will also moderate a panel of founders and advisors who have had dozens of exits among them.

You will be in a virtual room filled with people just like you, and get a chance to have questions answered by people who have been there.

“Things” Don’t Settle Down. You Do.

You don’t have to be consumed by work 24/7. But most people have a hard time letting go on their own. And the things they try—time management, productivity hacks—just tend to make the problem worse.

There is another way.

When you’re ready, let’s talk.

#exit #founder #founders #overwhelm

 

As a founder coach, I think about leadership and leadership styles a lot. One thing I often notice is how leaders, especially those heading companies, can gradually compromise their values in pursuit of higher goals. They might start as Ted Lasso, but more and more they end up like Walter White.

It’s easy to look at Ted Lasso, the incredibly hopeful, optimistic (maybe even naive) American leader of a British soccer club, and Walter White, the drug lord from Breaking Bad, as opposites. But reducing them to “Ted good, Walter bad” misses a crucial point. Their journeys and processes offer deeper insights.

Ted Lasso: Process Over Outcome

Ted Lasso’s leadership revolves around creating and nurturing a process. He emphasizes emotional, technical, and other forms of support, focusing on helping individuals be their best selves. Winning is not his main goal; it’s a happy side effect of a supportive environment and personal development. His influence is profoundly positive, fostering a great team and work atmosphere.

Ted’s philosophy is centered on the belief that a strong, supportive process leads to success. By prioritizing the well-being and growth of his team members, he creates an environment where everyone thrives. This, in turn, results in a successful soccer team and a fulfilling workplace. Ted’s leadership style highlights the importance of process, community, and personal development over mere outcomes. He doesn’t sacrifice his values for his goals—instead he creates an environment where both are supported.

Walter White: The Cost of the End Justifying the Means

Walter White, on the other hand, claims at every step of the way that his goal is to provide for his family. However, each choice he makes to maximize money for his family pulls him deeper into the drug trade. He equates leaving a large sum of money with providing for his family, but in the process, he destroys his relationships and, ultimately, his soul. His focus on the end goal of money leads him to sacrifice everything he truly values.

Walter’s journey is a cautionary tale about the dangers of prioritizing end goals over values and relationships. His initial intention to secure his family’s future becomes overshadowed by his descent into moral compromise and criminal activity. Breaking Bad is a brilliant and powerful reminder of the consequences of losing sight of one’s core values in the pursuit of success.

Real-Life Insights: Leading with Heart

I don’t know many real-life Walter Whites, but I do encounter people who mistakenly prioritize money, believing it will bring them what they want. This slow descent happens one decision at a time, and founders often end up compromising their true desires in the pursuit of financial gain.

One more weekend at work, one more trip that means you miss your child’s game or recital. Before long, your family no longer cares about your “sacrifices” for them. They’re just sad you never seem to want to spend time with them.

I spoke with a successful founder recently and asked him how he managed to avoid becoming consumed by his business empire. His response was enlightening: “The money is a side effect of doing the right thing.” This founder genuinely loves his team, suppliers, and customers, emphasizing that a happy, purposeful, joy-filled life naturally attracts financial success. You don’t need a big exit to fix everything when everything is already aligned and fulfilling.

Creating a Purposeful Leadership Journey

Does this resonate with you?

I’m hosting an invitation-only virtual roundtable on September 17th for founders to explore the concept of “the exit” and what lies beyond it. If you’re within two to three years of an exit, I’d love to invite you to join a small group of us live. Let’s discuss how to create a meaningful founder journey where financial success is a byproduct, not the end goal.

Reach out if this speaks to you