From Skateparks to Keynotes: Making Decisive Moves
There’s a moment in skateboarding that defines everything. It’s the second before you commit to a trick—the board is under your feet, your line is clear, your heart’s racing. You either send it or you don’t.
That same moment exists in business.
It’s the pitch you almost didn’t make.
The risky hire you debated for weeks.
The product you kept holding back on launching.
Over the last 20 years, I’ve realized that whether you're skating concrete or leading a business or a team, your ability to make decisive moves determines your trajectory.
*You’ll probably pick up my top CliftonStrenghts which I try leverage as much as possible in life and this blog 😅
1. See the Line Before You Roll
Before I drop in to start my run or approach a rail, I visualize the full line. The trick, the flow, the look and the feel and then the landing. In business, it’s no different. Although over the years I have obviously made irrational calls, or jumped into something sooner than I should have, being an Entrepreneur at heart, but over the years I have learned to think and act more strategic, still take action and not sit on an idea for too long but think it through and then act on it. I have learnt to not make random moves—but make strategic ones.
That’s the difference between activity and progress.
Strategy isn’t about long meetings or complex plans—it’s about seeing how the pieces connect before anyone else does. This is a skill or a talent however you want to name it, I have developed over time, but really started tapping into it only later in my career when I realized that I could fit the pieces together faster than others. That’s how I lead. I trust my gut, because it’s sharpened by patterns and insight. Also realizing that your strategy can change over time and how you roll it out sometimes needs to be agile, so does your thinking! The biggest mistake I have made is thinking I know that this thing and only this thing will work, until it doesn't! Making sure you ticked all the boxes and created a clear shared vision with your team and you implement the strategy in sprints 3-4 months I have found is the sweet spot, then revisit, revise, revitalize and GO! I’ve learned to move fast because I think deeply, keep in mind not everyone is thinking as fast as you, communicate the plan clearly and set clear achievable goals!
Lesson: If you want to make bold moves, start by training your vision. Don’t just react—anticipate.
2. Commit to the Trick
Hesitation kills. In skateboarding, that’s literal. If you half-send a trick, you’re more likely to slam. And O BOY, have I slammed! 9 broken bones, cracked shoulder, a bazillion sprained ankles and some other parts all blue and black but they shall not be named 🎱 moving on… you have to commit to the trick! Your mind knows there is a good chance of bailing, but your health and soul also knows the unbelievable feeling of landing that trick you have pictured in your head over and over and over! Just go do the Trick, be all in because if you arent all in you have a 90% chance of falling on your face or 🎱🎱…
Business works the same way. Overthinking is just procrastination dressed up as caution. Now I am fully aware that not everyone has a high risk appetite and we need to think things through to build strategy as we previously stated, but just go and DO THE THING! Very rarely something goes severely wrong that can't be quickly rectified, you need to believe in yourself and in your idea and go and do it! So many people say “oh I had that great idea” or “why didn't i do that thing that i wanted to” we honestly can't live life in regret and sometimes we just need a pair of 🎱🎱 and be bold and go for it! When I feel a move is right, I go. I’d rather adjust on the fly than wait for the perfect conditions that never come.
Bold action opens doors. Delay closes them.
*My Activator strength is a blessing: I don’t wait for permission. I light the fuse. Momentum matters more than mastery—because you figure things out when you're already in motion.
Lesson: The window for opportunity doesn’t stay open forever. If it feels right—go now.
3. Own the Outcome
Here’s the truth: no one’s coming to save you in the skatepark. You land the trick—or you eat concrete. You own it either way! Accountability when you are on the skateboard is part of the game, you can't blame the weather or your shoes for your bail, NOPE you have to own it because it’s YOU on the board and if it goes wrong chances are 100% it's your fault! Owning it recounting what went wrong, where did I not focus? Was my line wrong, be accountable for where it did and accept it , find a better way and move forward. You cant blame the curb for you not laning that grind because your balance was off, no go back sort your balance go nail that grind! This part of skateboarding is what keeps you grounded in humility because you learn that you have to take ownership of your decisions or indecisions.
That self-accountability I carried into my business life. Yes I have also blamed the accounts department for not collecting the fees, and the project manager for not managing stuff, we are all human but owning your domain, owning your decisions whether they are good or bad is a non negotiable! Early on in my career I was fortunate enough to have been in leadership positions and I had my fair share of peers and seniors blaming others for their mistakes, PLEASE don’t be that guy! Own your responsibilities! I don’t delegate the hard calls. I trust myself, even when the data is unclear and the path is foggy, I will own it all the way through. Something I keep reminding myself is that no matter if you are the CEO, the receptionist or the cleaner, someone is always watching and how you own your wins and losses defines your character! Respect as in life and business is earned.. make sure you earn yours everyday!
When leaders lack conviction, teams lose faith.
When you lead with clarity, even in chaos, people follow.
Lesson: You don’t have to be right every time—you just have to take responsibility every time.
4. Energize the Session
Even when you’re getting wrecked trying to land something new, there’s always that one skater hyping you up—pushing you to try again. This is another part of the skate community that I love! Random people rooting for you because they want to see you win! My best moments in skating were “That random guy” cheering with every bail, with every new try he yells… GO BRO GO, it energizes the hell out of you and also lets you know someone has your back and believes in you! I’ve always wanted to be that guy, in the park and in business.
Yes, I lead with intensity. But I pair it with belief. It’s always a battle to keep people truly motivated and honestly if team members aren't in the job or career they love they probably won't be, but this is where your leadership needs to step in and make sure that you have the right people in the right roles! I am blessed that my 4th top 5 strength is Positivity, so this “motivation” comes naturally to me, however getting the right people in the right places that I only learned long after Tony Robbins was an actual motivational speaker and Wolf of Wall street howls have run out. What I realized is When you're building something hard, optimism becomes fuel. When you work with true passion and purpose the people around you will automatically be energized and those who aren't will work themselves out of the equation. No need for 5min YouTube Motivational hustle videos NOPE, just passion and purpose and authenticity that's how you inspire and motivate! My crew knows I’ll push them hard—but I’ll never let them give up on themselves.
Lesson: Positivity isn’t soft—it’s fuel. If you want people to follow your decisive moves, lead with belief.
5. Skate Fast, Think Clear, Move Decisively
Decisiveness isn’t just about being bold—it’s about being prepared to live with your decisions, adapt as needed, and never lose momentum.
That’s what skateboarding taught me long before I ever signed a deal or hired my first employee.
So I’ll leave you with this:
Where in your life or business are you hesitating? What move are you seeing but not sending?
Because in both skating and leadership, the moment before the move is the most dangerous place to stay.
You already know what you need to do.
Make the move.