Theodore Roosevelt once said, “Nothing in the world is worth having or worth doing unless it means effort, pain, and difficulty.”

My take is this: good things come with challenges. And as a leader and entrepreneur, I know this to be true both personally and professionally. Stepping up into a leadership role—whatever it looks like—is not always easy. But that doesn’t mean it isn’t worth it! And while I can’t eliminate all challenges for you, I can bring a few to your attention that you need to be aware of.

6 Challenges Leaders Face

1. Managing People

As a leader, you interact with a wide variety of people every day. You may manage a team of employees, interact with clients, manage shareholders, and everything in between. Each stakeholder has different needs, desires, and goals. Learning to manage different stakeholders starts with listening. Understand where each is coming from and take the time to communicate well with each.

2. Prioritizing Your Time

You have a lot of demands on your time as a leader. Prioritizing your time and juggling competing responsibilities is key to your success as a leader. Focus on learning to distinguish what’s important versus what’s urgent. The key principle here is that not everything needs your personal attention—you can prioritize, delegate, or get rid of tasks that aren’t important. Eisenhower’s urgent/important matrix is a great intro to this concept.

3. Maintaining Balance

You need to be physically and mentally healthy to be most productive in your work. And that means finding a cycle of positive work-life balance and focusing on good self-care habits. To do this, you need to be okay with setting boundaries and saying “no” at times. Choosing to spend more time with loved ones, taking care of your body, and having fun with hobbies are all essential to “fill your cup up” to pour into other people you lead.

4. Working With People

I already listed Managing People but working with people and working well with people is another challenge in leadership. There’s no other way to say it—people are difficult. And let’s face it, we can be difficult too. As a leader, it’s inevitable that you’ll work with challenging customers, cranky suppliers, or high-drama employees.

You cannot avoid difficult people when you’re working together, but you can improve your communication skills. Patience, a listening ear, and clear conversations go a long way to smoothing over difficult situations. 

5. Setting Boundaries

Following from the last point—keeping healthy boundaries and having hard conversations that protect those boundaries is part of the role of a leader and one of the biggest challenges you’ll face. Practice may not make perfect but it will increase peace in your life as a leader. 

6. Growing Your Business

With all these other challenges in play, growing and nurturing your business is a challenge in and of itself. You need to learn to be proficient in both your interpersonal work relationships and business. Not everyone has natural business acumen, so surround yourself with wise mentors and people who can help you.

This is not an exhaustive list! As you can imagine, there are more challenges than you’d ever be able to predict as a leader. The key is to take each one as an opportunity to learn and grow. Focus on your goals and your “why,” and keep pushing through challenges as they arise. For more info about leadership and entrepreneurship, follow my blog at