Who's Riding Shotgun?

While working in a SaaS company for 12 years I had plenty of journeys. Some were actual road trips.  Picture this: two of us cruising down I-95 near Jacksonville, FL, headed to a big client meeting. It was supposed to be a straightforward upsell pitch, but of course, we were deep in a lively debate about data visualizations and who would be in the room when—whoops—we took the wrong exit onto 295. Neither of us noticed for a good 20 minutes, and by the time I realized we were literally going in circles, the GPS had that smug “might as well finish the loop” vibe. Cue the moment of panic—quick ETA recalculation (still going to make it on time) — followed by uncontrollable laughter. Sure, we weren’t the most efficient team in the world, but I wouldn’t trade that road trip companion for anything. When you're on a journey, it’s not just about getting there; it’s about who’s in the passenger seat when you’re accidentally going the wrong way!

When you’re navigating the bumpy roads of success, it’s tempting to feel like you have to drive the whole way by yourself. After all, it’s your journey, your goal, right? But those of us who have had some success will tell you: you’re not meant to go it alone. Success, especially when times are tough or goals are big, isn’t a solo sport. It’s more like an adventure—filled with twists, turns, and unexpected detours. And, like any good adventure, it’s better with someone riding shotgun to help guide the way.

Think about the most successful people you know. Chances are, they didn’t get where they are without a little help. Take Steve Jobs, for example—the iconic leader behind Apple. His partnership with Steve Wozniak wasn’t just crucial to Apple’s founding; it was the collaboration that made Apple what it is today. Jobs had vision, and Wozniak had the technical genius to make it happen. Together, they created a legacy. That duo, while not always perfect, is a great reminder that having someone beside you can fuel your success in ways you might not achieve on your own.

Why You Need a Partner on the Road to Success

Athletes have coaches; entrepreneurs have mentors. Even superheroes have sidekicks. We all need a trusted companion—a sounding board, a guide, or just someone who brings out the best in us. I have always needed someone who I felt comfortable saying all my crazy ideas out loud to. When the road gets rocky, a strong partner can help you regain focus and steer you back on course.

Having a 'shotgun rider'—someone who’s with you, helping you read the map, challenging you to take the right turns, and celebrating with you when you hit milestones—can be the difference between a detour and a breakthrough.

Finding Your Shotgun Rider

1. Look for Shared Values and Vision
   The best partners share similar values and can see your vision for success. They don’t need to be on the exact same path, but they should understand and support where you’re headed. Look for someone who believes in your mission and who you trust to help you course-correct when necessary.

2. Seek Out Someone Who Complements Your Strengths
   Your shotgun rider should not be a replica of you; they should complement your skills. Maybe you’re great at big-picture thinking, but struggle with the details. Find someone who thrives in that space. A balanced partnership will help you see things from new perspectives.

3. Don’t Be Afraid to Ask for Help
   Whether it’s a mentor, coach, or colleague, don’t shy away from asking someone to ride shotgun. Sometimes, just having someone there to bounce ideas off or to help you maintain your mental resilience can make all the difference.

4. Stay Open to Growth and Learning
   The best journeys are the ones where you grow along the way. A good partner will challenge you to evolve, stretch your limits, and encourage you when things get tough. Pick someone who pushes you to be better.

Make This Journey an ‘Adventure’

Sure, a journey alone can be empowering. By definition, a journey is an act of traveling from one place to another. But what if you looked at your success quest as an adventure instead? That changes the mindset. Adventure is defined as "an unusual and exciting, typically hazardous, experience or activity."

I don’t know about you, but I’d rather have someone with me for the exciting stuff and the hazardous stuff! Adventures are better when shared. So, whether you're starting a new venture, working on a big project, or simply trying to figure out the next steps in your career, treat it like an adventure and think about who’s in the passenger seat. With the right person riding shotgun, not only will you reach your destination, but you’ll enjoy the ride a whole lot more.

Who’s riding shotgun on your journey to success?