I’ve been a team leader more than once in my career.
I’ve been a section editor leading a team of writers and journalists.
I’ve been a camp counselor leading a team of pre-teens through the woods.
I’ve led teams of tour guides, digital marketers, fiction editors, and more throughout my years in the workforce.
And now, as a freelancer, I lead a team of other freelancers who keep my business on its feet.
But even though it feels like I’ve learned how to lead a team a million times over, there are always aspects of it that surprise me.
Sure, I enjoy the extra responsibility, the support of a robust team, and the additional income that usually comes with a leadership position.
But it’s challenging in so many ways I didn’t expect.
There are some things people should know about how to lead a team before they take on a management position. Here are the harsh truths about leadership, and my tips on how to overcome them.
Personalities play a huge role, and they are unpredictable
You can read all sorts of books or listen to a dozen podcasts about how to lead a team, but so much of what you’ll learn won’t be applicable to your situation.
That’s because every team is unique—and I don’t mean that in a sappy “everyone is special” way. I mean that as a leader, you are going to be dealing with a wide range of personalities and behaviors, and there’s nothing you can do about it.
As a team leader, you might have some input on who gets put on your team. Though until I started freelancing, I found the decision was usually mostly up to my (often terrible) bosses, who made (often terrible) decisions on my behalf. Or else I’d be hired onto a team that already existed, and would have to work with them regardless.
And even if you do get some say in who you hire, you can’t really know what a person will be like to work with, even if you read their resume meticulously and put them through multiple interviews.
As a leader, it is your job to help every member of the team bring their best, which also means adapting your own methods and behaviors to meet them where they are. Of course, you don’t have to accept unprofessional or abusive behavior under any circumstances. But you also must learn to read between the lines at work and understand people’s personal quirks, perspectives, and experiences to be an effective leader. In your one-one-ones and interactions with team members, pay attention to more than just their KPIs and tasks. Ask them questions like: Actively listen to their answers, and consider how their behaviors mesh or or clash with the others on the team. This will help you decide which team guidelines to roll out, playing to your diverse teams’ strengths.The Solution: The only way to overcome this is to adjust your own personality. Learn how to roll with the punches and accept people as they are, which is way, way easier said than done.
It’s lonely at the top (and dangerous to step down)
One of the harshest truths I’ve learned about leadership is just how isolating it can be.
When I became section editor, I expected to still be “one of the gang” to the other writers, just with a fancier title. But almost overnight, the dynamic shifted.
The team members I used to grab beers with suddenly held back their honest opinions in our conversations. Casual venting sessions stopped when I walked into the room. And I found myself constantly second-guessing whether I should join certain social gatherings or if my presence would change the atmosphere.
What nobody tells you is that leadership creates an inevitable distance. You can be friendly, approachable, and genuinely care about your team, but you can’t fully be their friend in the same way anymore. You’re privy to information they aren’t. You have to make decisions that might disappoint them. You have to deliver feedback that might sting.
In other words, the social part of work life can come to a screeching halt once you take on a leadership position.
Second, be intentional about creating appropriate social connections with your team. Host occasional team outings where you can be more relaxed, but maintain awareness of your role. I’ve found structured activities like escape rooms or volunteer days work better than open-ended happy hours where boundary lines get blurry. Third, find outlets completely outside your work circle. Work friendships are overrated anyway, as they often fall apart once one person leaves the company (or gets promoted). This article is chock-full of ways to make friends as an adult (without relying on work).The Solution: Accept the distance as part of the role, but find ways to mitigate the isolation. First, build relationships with other leaders who understand your challenges. When I was directing the marketing team at the agency, I formed close relationships with two other heads of department. We could share frustrations and advice without compromising our leadership positions.
The higher you rise, the fewer safety nets and guides you have
As I found myself climbing the corporate ladder, a strange and unexpected thing happened: my support system began to shrink dramatically.
When I was just starting out at the digital agency, there were training programs, onboarding sessions, and detailed guides for everything. My manager checked in regularly, senior colleagues were happy to answer questions, and there was always someone to catch me if I fell.
But with each promotion, the safety nets disappeared one by one. By the time I became Director of Content Marketing, I realized no one had prepared me for this level of responsibility. There were no handy manuals, no training programs specifically designed for leadership positions, and suddenly very few people I could turn to for guidance.
My boss expected me to figure things out independently. The company wouldn’t fund leadership training because they assumed I already had those skills (why else would they have promoted me?). And I couldn’t exactly admit uncertainty to the team looking to me for direction.
The irony was striking: The higher I climbed, the more precarious my position felt. I had more autonomy and decision-making power, which was exhilarating, but also terrifying when I realized I was now expected to navigate complex situations without a roadmap.
The lack of structure at higher levels isn’t a sign that you don’t deserve to be there. It’s simply the reality of leadership positions, and recognizing this challenge is the first step to overcoming it.The Solution: When you find yourself in this position, you need to actively create your own support structure. Here are resources that have been invaluable to me:
Work follows you everywhere (even if you’re hourly)
I was having dinner with my brother-in-law recently, watching him completely relaxed after his workday in IT support. As an hourly worker, when his shift ends, his job responsibilities end too. He clocks out, goes home, and doesn’t think about work until he clocks in again the next day.
This fundamental freedom disappears when you take on a leadership role.
As a tour guide team leader at my college, I was technically still paid hourly. But unlike my fellow guides who simply showed up for their assigned tours and went home, I was constantly thinking about scheduling conflicts, training new guides, addressing parent questions from yesterday’s tours, and preparing for next week’s special alumni event. (And don’t even get me started on balancing work and school life.)
The same pattern repeated in every leadership position I’ve held. When you lead a team, your brain doesn’t clock out at 5 p.m. The concerns become longer-term and more complex. You’re not just solving today’s immediate problems—you’re anticipating next month’s challenges, planning for next quarter’s goals, and worrying about your team members’ career development.
You must actively create separation between work and personal life before the two completely merge. This means being disciplined about when you check messages, setting clear expectations with your team about your availability, and creating specific shutdown rituals that help your brain transition from work mode to personal mode. It also means being intentional about truly unplugging during vacation time. Your team needs to learn to function without you—and you need to learn to trust them to do so.The Solution: The only solution here will sound very cliche. You need to establish boundaries that give you a better work-life balance. But trite as that may read, this is really the only way around this challenge.
Check out these other resources to help maintain your work-life balance as a leader:
Leadership is a continual journey of growth, adaptation, and self-discovery. While the challenges I’ve outlined might seem daunting, they’re also opportunities to develop resilience and wisdom that extend far beyond your professional life.
The distance from your team, the lack of guidance, the blurred work-life boundaries—these are the realities of leadership that nobody advertises in the job description. But by acknowledging these challenges head-on and implementing thoughtful strategies to address them, you can become the kind of leader who not only succeeds but helps others rise alongside you.
