While it may not always seem like it, successful nonprofits are run more or less like a business. Yes, we have some regulatory requirements that are a bit different. Yes, we have to think much more about our potential customers in segments of clients and donors. Yes, our money often comes more from relationships than from discrete products. But from the day to day, a nonprofit is still a business, and it requires leadership and strategy just like any other. 

Lately, I’ve encountered a challenge that is no new experience for the small business leader: my current skill set doesn’t fully align with the job I need to get done. Yes, I have the leadership skills, but since I come from a less traditional background, there are some business concepts that don’t come easily to me. So like any good entrepreneur, I began to identify my resources, leveraged my network, and started to develop an action plan.

Are you facing a similar challenge? Perhaps you’re solving a problem for your massage therapists, but you’ve never served in a clinical role before. 

Here are the top five habits I found for leveling up when faced with a challenge you’re not sure how to solve: 

Habit 1: ASK

I don’t know if you’re like me, but I love to know things. I really like having the answers and being good at things, so asking for clarification doesn’t come naturally to me. Maybe it does to you, and if so, you’re already in a great spot! 

But if you’re like me, you may need to prioritize asking for help. Identify five to ten people who have unique knowledge in the area you need to figure out. Then ask these folks if they’d be willing to trade their knowledge and company for a good cup of coffee or their favorite lunch. Then go into that meeting with a clearly-defined explanation of what your challenge is, some potential solutions you’ve devised, and a willingness to listen. Answer any questions those folks have, ask follow-up questions to make sure you understand all they’re saying, and just listen. Don’t expect that you’ll have an answer at the end of the conversation, but instead just take the information in, and add it all together. Chances are after all the conversations, you’ll have a sense of in what direction you should proceed.

Habit 2: READ

I know, I know. You don’t have time to read. But you actually don’t have time not to. Listen to audiobooks if that relieves some stress about taking time to read. You can even speed audiobooks up to get the reading done faster. There are hundreds of books on most services and with many, you can listen to multiple books at once. I keep at least two professional and two fun books at once, as well as podcasts to increase my professional learning. I even turn my car into a classroom by listening while I drive. 

Habit 3: CONVENE

Set a regular gathering with people who have the expertise that you’re seeking. I’ve started meeting weekly with a friend to discuss business books and concepts and talk through challenges we’re facing. You could go to a meetup group or find an online community where you can ask questions–whatever works for you! Just get together with people who can help! 


Once again, I know that you don’t have time. I’ve heard it before. And I’ve felt that way before. Now, I block off time to exercise a month in advance so that I don’t miss it. I’ve made it my priority to workout because when I do, I find that I have more breakthroughs, more moments of clarity, and more emotional bandwidth to deal with challenges. Plus, the brain science supports it. If that’s enough, know that you’ll walk away feeling like you can do anything–including figure out your job! 

Habit 5: START

Whenever you’re facing a challenge, it can be tempting to clean your house, straighten your desk, organize your digital files, or otherwise…put things off. But the honest truth is that it’s easier to just start. Figure out whatever the smallest piece is and get going. Or if you’re a more “eat the frog” kind of person, then start with the scariest piece. Just find something and start. You’ll find that the momentum from starting with one task will spur you to tackle others while you’re at it, and that having something for others to react to is much better than just a vision.