The Weight of Your Baggage: Why Your Trust Issues Are Holding You (and Everyone Else) Back

We all have baggage. It’s just a fact of life. We’ve all been through shit in our lives that we’d rather not go through again. The memory of that shit and the feelings associated with it are our baggage. And the heavier that baggage gets, the more likely it’s going to weigh down not just you but your entire team.

Now, I get it. As a leader, you’ve probably been burned before — someone dropped the ball, a deadline was missed, or maybe an important task was done almost right but not in the perfect way your inner control freak would’ve preferred. I’ve been there, too. As a new project manager, my director gave me a “senior” resource to help me on my very first project. Then, proceeded to tell me that he really needs to be “managed.” Huh? I guess by “senior,” he didn’t mean in terms of experience, but more as in age.

Needless to say, it didn’t go well. Deadline after deadline was missed. As the person who interfaced with the client, I was constantly apologizing, feeling helpless. Finally, just trying to be honest, I told them I wasn’t able to manage the resources that had been assigned to the project and guide them to do what needed to be done. I would learn how to do it myself and do my best to meet their expectations.

After a few more of these experiences, my subconscious mind whispers: “If you don’t check every detail, something’s going to go wrong again.” Before you know it, I became the helicopter PM, obsessively monitoring, correcting, and second-guessing my team like a helicopter parent at a playground.

If you’ve experienced these whispers and subsequent behaviors, then, my friends, you have the kind of baggage that’s not just inconvenient — it’s blocking your path. In fact, your trusty sidekick, fear of failure, is practically steering the ship.

Here’s the kicker: While you’re busy worrying about whether things will get done “the right way” (read: your way), you’re unintentionally choking the very trust you’re trying to build with the team members. I mean, sure, you say you trust your team. (I believed I trusted my team.) You delegate (well, technically). You give them the space to take the lead… right up until you swoop in and “just check” on the progress. Because, let’s face it, you’re not really sure they can handle it (or at least handle it as well as you could.)

Spoiler alert: Your team notices. They always notice.

Even if you haven’t explicitly said, “I don’t trust you,” your actions — your constant hovering, the subtle corrections, the detailed instructions that leave no room for creativity — are shouting it from the rooftops. And trust me, nothing kills innovation and initiative faster than a leader who gives the illusion of trust but keeps their hand firmly on the steering wheel.

The irony? You want your legacy to be one of empowerment. You want to leave behind a team capable of leading in your absence. But that legacy won’t happen if your team’s biggest lesson from you is, “Don’t worry, the boss will fix it.” What you’re leaving behind is the message that only you know how to do things right, and everyone else just better not mess it up.

Unpacking Your Baggage

So, how do you unpack this baggage? Well, first, you’ve got to recognize that this fear of things going wrong is exactly that — your fear. It’s based on your past experiences, not necessarily the current situation. And like any irrational fear, it needs to be confronted head-on.

Try this: The next time you feel the urge to micromanage or swoop in to “rescue” a project, take a deep breath and… do nothing. Yeah, you heard me. Let it play out. Maybe your team won’t do things the way you would, but guess what? That’s the point. They need to learn, grow, and find their own way. And sometimes, that means letting them stumble a bit.

The real legacy of leadership is teaching people how to think, not how to follow a script. When you stop allowing your baggage to dictate your actions, you free your team to step up, take ownership, and (wait for it) actually earn your trust. The trust that’s built not from micromanaging or correcting but from letting go and allowing people to show you what they’re capable of.

After all, isn’t that the leadership legacy you’d want to leave behind? One that empowers others to act, not because they’re afraid of messing up in front of you, but because they genuinely believe they can.

So, unpack that baggage. Let your team rise, even if it means a few bumps along the way. Trust isn’t just given; it’s built — and it’s built in the space where you stop worrying about every detail and start believing in your people.

You CAN do it! Yep, you’ll mess up, stumble, and maybe even fall flat on your face. But through this process, you will learn. You can’t expect to experience the highest highs if you aren’t willing to experience the lowest of lows. You must experience darkness in order to fully appreciate the light. ??

Next Month

The paradox: Trust starts from the inside. To build a lasting culture of trust, you’ve got to become self-aware enough to recognize what’s driving your own behavior. In the next article, we’ll take a deep dive into how to uncover those hidden triggers and finally start leading without the baggage.