If you think you "deserve" to lead, then you probably don't. 😬
😬😬😬
Our culture is obsessed with milestones.
✅ Going to and finishing college.
✅ Getting married.
✅ Buying a house.
✅ Having kids.
☠️ Retiring at least a year before the day of your funeral service.
The obsession over milestones and meeting the expectations to hit them has given birth to a mess that I’m not sure we’ll ever recover from as long as we exist on this mortal coil — from national housing crises to college graduates with crippling student loan debt to getting married way too early.
(As someone who got married at 24 — and admittedly still married, and happily at that, shut up — kids in their early 20s have no business getting married, ESPECIALLY in order to check a box or meet someone else’s expectations.)
There’s another milestone in there. We don’t talk about it a lot, but it’s there.
THE MILESTONE WE NEED TO TALK ABOUT
As I chew on the concept of “Oddball Leadership,” and what the future of it looks like, I’ve been reflecting on what has predominantly shaped my leadership style. What inspires me to lead with belonging, gratitude, curiosity, and joy.
(Because nothing about my management style has been taken from a book, or from a professional development seminar or a training module.)
Honestly, a lot of my leadership style has been influenced by my experiences in the workplace. Working for good bosses, and bad ones. Emulating their likeable traits and tendencies and casting off the ones that really sucked.
Unfortunately, I’ve found that most of my bosses were unprepared and unfit for leadership. In general, I would even argue that most people are unprepared and unfit for leadership.
But why?
Because we talk about climbing The Corporate Ladder like it’s a life event that everyone should experience. Like getting married or buying a house.
When we talk about moving up the ranks in a company like it’s a grand milestone, of course people who have no business being managers are going to seek roles in management. Usually without doing the work of honest introspection and assessing one’s fitness to lead a team.
They think they deserve it simply because they want it. And they want it because “everyone should want it.” Or because “it’s the next step” in their career.
And/or they want to challenge themselves.
And/or they want the title. The accolades. The pay increase. The perfect LinkedIn profile. The power. The ego boost.
I’m sorry, but these are the wrong reasons for pursuing a role in team leadership.
The obsession of getting to the top, at any cost, simply perpetuates the milestones mess we’re already in. And the cost often comes at the expense of those who are led by someone who wants to lead for some ill-intended, self-important purpose.
IF I’VE SAID IT ONCE, I’VE SAID IT A MILLION TIMES.
Team leadership, from a personnel management sense at least, is not for everyone.
And not everyone is built to lead a team or manage people. Milestones be damned.
Team leadership is quite hard, if you go about it in the right way — to an extent that most adults should be turned off completely, if I can be honest!
Because it requires sacrifice.
Seemingly unlimited reservoirs of empathy and patience.
It takes compassion, curiosity, joy, and all the things that make Oddball Leadership…well, odd.
And nobody thinks about that when all they want to do is climb The Ladder. To be the person in the big chair, with the title and the power and the corner office.
But can we truly blame these people?
A lot of managers who have no business being managers are simply buying into what they’ve been told is the “right thing to do.” So we can’t necessarily place blame on folks who are just poor, misled Ladder-Climbers.
Shouldn’t we instead be challenging the notions that set up The Ladder in the first place?
WHAT I’VE LEARNED FROM THIS BROKEN SYSTEM
There are a few hard truths I have learned when assessing the professional world’s deficiency in effective managers.
Management positions should not be reserved for people who do their best work in performing the tasks required to do a technical job. The skills and knowledge necessary to adeptly perform a task-based job won’t do you any good as a manager if you aren’t dedicated to ensuring psychological safety in your office culture or showing appreciation for the team. Or leading with curiosity during difficult conversations.
We must acknowledge that taking a management position is not taking a promotion; it’s taking a vow. So much emphasis is placed on climbing The Ladder that no one seems to have the time or the energy to talk about how truly difficult managing is. It demands deep commitment, and fidelity, and selflessness.
We shouldn’t look down upon those who don’t want to lead. I once worked with someone who felt forced into a management position during a sudden and immediate staffing change — and they hated it. Ultimately they knew leadership was not for them. The kicker? They were a damn good manager in that position. But management should never be forced on someone — remember, not everyone wants to do it! And that is okay!
SO MAYBE THE MILESTONE WE HAVE TO CHALLENGE ISN’T MARRIAGE, HOMEOWNERSHIP, OR EARLY RETIREMENT.
Maybe it’s ascending the org chart.
Because it’s more than asking “What’s next for me?”
It’s a commitment — one that should be entered into slowly, intentionally, and with a clear-eyed understanding of the weight it carries.
One that requires you to ask yourself, “Am I willing to be responsible for others?”
If the answer is yes — welcome to Oddball Leadership.
(And if the answer is no — or not yet — that’s not a failure.
That’s wisdom.)
