Introduction to Winning, Losing, and Redefining Success

Dwayne “The Rock” Johnson is credited with saying, “Be Humble. Be Hungry. And Always be the Hardest Worker in the Room.” Whether in business, on the field, in the classroom or in the weight room, I have always had an inert drive to win, even if not overtly stated. I would just quietly go out and do the work. I was never really looking for praise, but did expect there to be fruits of my labor, which could be as simple as “atta boy!” or as grandiose as world domination.

The Early Days of Ambition

I remember one of my favorite shows as a child was, “Pinky and the Brain.” The character Pinky would always ask Brian what they were going to do that evening. Brian would always say, “What we always do: try to take over the world!” I’m like, “Yeah – I get that.” As you can imagine, my efforts of world domination did not often work out. Thankfully, there were always people who were smarter or faster or more gifted than I was, which often humbled me. I am extraordinarily grateful for that, partially because I am really disinclined to deal with the aftermath of world domination, and more importantly, there are more lessons to be learned from losing than winning.

Lessons Learned

Here are some of the things that I have learned about winning, losing and redefining success after 54 trips around the sun:

1. Winning isn’t everything. It’s the only thing. I don’t see the point of getting up in the morning if I am not going to pursue winning at something. Winning doesn’t necessarily mean that someone has to lose, but simply, the idea of making someone feel seen and heard is a win for me. Feeling good about what I accomplished for the day is a win. Closing a deal is a win. Booking a new podcast guest is a win.
2. Don’t Minimize / Don’t Lower Your Standards. When growing up before the world got soft, parents would say, “If all of your friends jumped off the bridge, would you jump, too?” No one else can define what success is for you. My standard is excellence. Do I always hit it? No. Do I always strive for it? Absolutely. Do people tell me that I don’t have to / shouldn’t work that hard? Yep. Do people say it isn’t worth it? There are books on it.
3. Losing isn’t the end. While there are many that would suggest that life shouldn’t be that simple, unfortunately, it is. One of my favorite quotes from Dale Earnhardt is, “Second place is just the first loser,” or from the move Talladega Nights, “If you aren’t first, you’re last!” Think about it: the person that came in second usually feels like if they had made some adjustment, they could have come in first. The horizon is closer for them than probably anyone else on the field. So what do they do? They work harder so that next time, they are more likely to win. That should be the case with any position on the field. If you are losing, you need to understand why and find out what you can do to win.
4. I can’t be the best at everything. Honesty, I will definitely try. As a weight lifter, my weakest lift has always been my bench. I have long arms, I’ve injured my shoulders several times and by design, I just don’t have the anatomy of someone who can bench heavy. However, there are many other exercises where I am extremely capable, and if you look at my overall capabilities, it exceeds that of most humans. What I’ve learned was that while I shouldn’t ignore the things that I don’t do well (think about weight lifters with big upper bodies and skinny legs), I need to be very clear about where I can win and where I can’t.
5. I must define what it means to win. For me. No one else can define what winning means to me. I would be foolish to let someone else do that or compare myself to other people. Both are recipes for disaster. If you think about the Guinness Book of World Records, people find very specific, narrow categories to be the best in the world at. Who would have thought that there would be a record for the farthest throw of a washing machine (14ftm, 7 in by Johan Espenkrona: As a business owner, it would be futile for me to say that I could run the best consulting firm in the world. The idea is too broad and is subjective. But to say that I want to build the best strategy and operations consulting firm targeting inspired founder-led growth stage companies in the country – that would be more feasible.
6. Winning is an event. As any Olympian will tell you, once you’ve won at something, even if you are the best in the world, the win is over. You have to either do it again or carry it as a fond memory. Keep in mind that whoever came in second place is gunning for your position. It’s almost funny: Tom Bradey seems to be the only person still talking about the Patriot’s dynasty. Boston isn’t having parades every day. The NFL has moved on. If I want to keep winning, I have to keep working. Even the GOAT will be replaced and only a memory at some point.
7. What got me here won’t get me there. Nothing remains the same except that fact that things will always change. Societal, technological, economic, environmental and technological changes will happen, in addition to my own perspectives, capabilities and capacities. How I drive now has changed (thankfully) between the time I was 18 and now. However, weather, traffic, time of day and road conditions all impact my drive. I cannot drive in the rain in the dark the same as I would during the day on a bright shiny day. Note that the destination doesn’t change. Because of the environment, I need to adjust how I will reach it.
8. Don’t get lazy. This is critical. As stated: winning is an event and what got me here won’t get me there, just because I won in one area doesn’t mean that I can coast. If anything, it means that I need to work harder. Why? Because if I am in a competitive environment, someone is going to analyze why I won and they lost, and will adjust their strategy to be more likely to win. They won’t because I will anticipate their strategy and adjust my own while continuing to get better at what I do. If not in a competitive environment, if I don’t raise the stakes, I will get bored and will likely stop.

Conclusion

One of the things that I love most about being an entrepreneur has been the nearly constant growth opportunities that I have had. I am the type of person that needs to have a new challenge to overcome, or a new puzzle to solve. As an entrepreneur for more than 30 years, the learning has been nearly unlimited. I would caution you, though: what works for me and what appeals to me doesn’t necessarily work for you. I have always found that when in a situation, I keep what works for me and toss the rest. What will be consistent is the ability to embrace winning, losing and redefining success.

FAQs

Q: What is the most important lesson you have learned about winning and losing?
A: The most important lesson I have learned is that winning isn’t everything, it’s the only thing, and that losing isn’t the end, but rather an opportunity to learn and improve.
Q: How do you define what it means to win?
A: I define what it means to win by setting specific, narrow categories for success, and not comparing myself to others.
Q: What is the key to continuous success?
A: The key to continuous success is to never get lazy, and to always be willing to adjust and improve your strategy to stay ahead of the competition.
Q: How can I apply these lessons to my own life and business?
A: You can apply these lessons by setting clear goals and standards for yourself, being willing to learn from your losses, and continuously working to improve and adapt to changes in your environment.

In a world dominated by online courses and certification platforms, one old-school concept is quietly making a powerful return: learning by doing.

On-the-job learning—also known as experiential learning or just-in-time training—is becoming the go-to strategy for companies that need their teams to adapt faster, think critically, and stay ahead of constant change. From Fortune 500 firms to lean startups, employers are rethinking how training is delivered—and realizing that real-time, role-based learning often beats one-size-fits-all programs.

The Shift From Classroom to Context

What’s changing in 2025 isn’t just what we learn—it’s how we learn. Instead of pulling employees away from their work for traditional training, more companies are embedding learning into the flow of work. Think:

• Team-based simulations and live problem-solving sessions

• Internal “coaching sprints” for new tools or processes

• Shadowing and peer mentoring built into onboarding

• Bite-sized learning resources integrated into workplace platforms

This model meets employees where they are—busy, juggling priorities, and needing answers in real time. It also drives stronger retention and engagement because the skills are immediately applicable.

Why It’s Working

Companies embracing this shift are seeing results. According to a recent LinkedIn Learning report, organizations that invest in on-the-job learning see a 24% improvement in employee performance and a 29% increase in internal mobility.

And it’s not just about upskilling. It’s about creating a culture where curiosity, coaching, and collaboration are part of everyday work—not special events reserved for leadership or L&D teams.

The Role of Managers and Teams

This model only works if leaders play their part. In 2025, the best managers are doubling as learning facilitators. They’re not just assigning tasks—they’re setting the stage for growth by:

• Encouraging reflection after big projects

• Creating space for team members to teach each other

• Giving stretch assignments that come with real support

• Helping employees connect their goals to business outcomes

It’s a more hands-on, relational approach to development—and it’s helping teams stay agile in a fast-changing world.

Final Thought:
Work isn’t slowing down. If anything, it’s getting more complex. That’s why companies that treat everyday work as a learning opportunity—not a disruption—will build the most capable, confident teams. In 2025, the smartest thing you can do for your workforce might just be letting them learn on the job.

Stay tuned to WORxK Global News for more insights on how training is evolving and what it means for your organization’s future.

In a business world obsessed with speed—fast decisions, rapid scaling, instant results—a growing number of leaders are embracing something different: restraint.

Slower leadership doesn’t mean indecision or delay. It means making room for reflection, deeper collaboration, and intentional action. It’s about knowing when to pause—not because you’re stuck, but because you want to move forward with clarity.

And it’s proving to be one of the most effective strategies for long-term impact.

Rethinking the Pace of Progress

Many teams are burned out from reacting to one thing after another. Constant urgency can leave employees scrambling and leaders making choices that are reactive rather than strategic. Slower leadership pushes back against that culture of constant acceleration.

It invites space to ask:

• Do we actually need to make this decision today?

• Have the right voices been heard?

• What long-term outcome are we trying to create?

The goal isn’t to stall—it’s to lead with intention.

What It Looks Like in Practice

We’re seeing leaders shift their approach in subtle but powerful ways:

• Starting meetings with a moment to clarify purpose, not just agenda points

• Delaying a product launch to allow for broader team input

• Refusing to treat every problem as a fire drill

It’s not always flashy. But it builds trust. It protects energy. And it leads to smarter choices that last.

Why It Matters Now

People are tired of constant pivoting and rushed rollouts. They want to be part of workplaces that value depth over speed. Leaders who embrace this mindset create cultures that are more thoughtful, more resilient, and ultimately more effective.

And when a leader models calm under pressure, that energy trickles down.

Final Thought:
Slower leadership isn’t about doing less—it’s about doing what matters, better. In a time when everyone else is racing, the leaders who pause with purpose will be the ones who move forward with power.

Follow WORxK Global News for more insights on leadership, decision-making, and culture-building in today’s workplace.