How to know who won’t leave you on an island.

We live in a social media driven world where our best Friends, Connections, Contacts, Followers and Matches are a click or two away.  Because we’re so accustomed to living the “American Dream,” keeping up with the Joneses, and subjecting ourselves to the rigors that accompany these conquests, we’re content keeping up through surface-level digital footprints and sporadic, quick in-person or phone interactions.  How many times per day do the, “How are things?” – “Good. You?” surface-level, efficiency-driven interactions play out? We think we know what’s going on, but all we just know what people want portrayed out there because we don’t expend the time to go deeper.

Thousands of contacts connected within a few clicks but how do we know who will come through for us when it’s on the line? Who’s willing to take the time and put in the energy themselves to go the extra mile for you when you’re in a time of need – and then actually follow through?

We’re at an ugly crossroads in America. We see it amongst all the political dissension.  We see it as mental health traumas rise. We fight over resources to the point of disassociation with those closest to us. We can’t go deep ourselves, so how could we go deep for others? Are we in it for status or the good of human kind?20170309_133358

Sandwiched in-between two personal quests for ownership after putting it all on the line, I took a trip. Despite better financial judgement, I joined college friends south of the border for the sake of a friend who’s always had the ability to go deeper (Kaveh is pictured right with our chauffeur Carlos).

After some tropical guy’s weekend introspection, I came to some harsh realizations. I’m great at the surface level stuff, but like many guys, I have trouble talking about feelings, needs, concerns, etc. I’m too trusting that if I put it all out there for you, that you will then come through for me. I learned that I try to formulate solutions for everything and in doing so, force things when the square pegs will never fit into the round holes.

With that said, though, I learned that sometimes you need to put people on the spot to realize how much you can count on them. Sometimes, you have to lean on yourself alone.

Paying it forward with no expectations is hard to do but pays big dividends. I recently watched The Kindness Diaries on Netflix, which details one man’s quest to cross the world on a motorcycle with no money relying on the goodheartedness of others.  Despite lots of doubters and strifes along the way, Leon made it and repaid those with pressing needs who helped him out handsomely with something that would help get them across the hump. That begs the question, if strangers with very little can do it, why can’t we?

What can you do to interview and determine who’s trustworthy and will come through for you? What are some strategies you’ve used to dig deep and get results during times of need?

 

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Author: True North Team Consulting

About Charles Reynolds I’ve spent my career at the intersection of sports business, leadership, and entrepreneurship—working inside fast-moving organizations, advising teams and founders, and learning firsthand how pressure, ambition, and uncertainty shape decisions. Over time, my work has evolved beyond titles or industries. What consistently shows up is this: people don’t struggle because they lack talent or drive—they struggle because they lose clarity about what matters, where they’re headed or results they're after, or how to move forward without burning themselves out. That’s where I focus my work. I help leaders, founders, and high-performing individuals think clearly, align their actions with their values, and make better decisions when the path isn’t obvious. Sometimes that looks like strategic advisory. Sometimes it’s coaching. Often, it’s simply creating the space and structure for honest reflection and momentum. Travel has played a quiet but important role in shaping how I see the world. Experiencing different cultures, systems, and ways of living has reinforced my belief that growth—personal or professional—comes from perspective as much as performance. That belief shows up in my work, my writing, and how I engage with others. I care deeply about transparency, holistic sustainability, and lifelong learning. I’m drawn to questions around purpose, leadership under pressure, ethical and personal growth, and what it means to build something meaningful without losing yourself in the process. This site is a home for my thinking—across leadership, business, life, and direction—and a place to connect with people navigating similar questions. If you’re building, leading, or re-orienting or just exploring, I’m here to help.

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