Choosing a Meaningful Career Path


We all have several great careers within us. We could be entrepreneurs or educators. We could work in international development or investment banking. These careers could all lead to meaningful work. The greatest challenge many of us have is simply picking one.

For the professionals I’ve worked with to build a more meaningful career, one of the hardest things for them to do is commit to pursuing one career path. My coaching clients often have several different career interests that they want to pursue all at once. They feel like now is the time to explore before they get stuck going down one route. Yes, it’s so important to have a good assessment of which opportunities are best suited for you. But, when you’re ready to land a job, it’s time to pick one path and pursue it. Here’s why:

There’s No Right Answer

There is no perfect job out there waiting for you. There are several great jobs, but you don’t land a perfect job. You build it once you have a job. So, don’t get caught up wondering which path will lead to the best job. Just pick one and focus on finding a great job. The worst thing that can happen is that you find out you’re on the wrong path, learn a lot from that experience, and go down a different path.

Focus Beats Coverage

It’s tempting to invest time and energy developing all your different career paths so that you don’t miss any opportunities. But, if you’re putting 50% of your effort into two different paths, what are the chances that you land any of the opportunities you find? It’s better to stay focused on one career path. You’ll see fewer opportunities, but your chances of converting are much higher.

Momentum is Key

Many people treat pursuing career paths like picking which slide to go down at a water park. They think that once you commit, you’re stuck on that slide. But I see exploring career paths more like riding a bike. You slowly build momentum in a certain direction. If you’re going roughly the right way, you can always adjust your course and your momentum will quickly carry you in that new direction. Exploring a career path is no different. The connections you make and projects you work on are all building your career momentum. It’s easy to leverage these things if an unexpected opportunity arises or you decide to pursue an adjacent career path.

Hopefully, this gives you the confidence to pick a career path and get started! The only time I advise against getting out there is when you have no idea what type of work you’re interested in pursuing. It’s important to have a general idea of what really matters to you in your next job. That way you can evaluate whether you’re on your way to an exciting, meaningful career.

At Mission Driven, we offer career accelerator programs and coaching to help professionals figure out what really matters to them. If you’re interested in working with us, feel free to drop me a note.

Start with Why when Exploring a Meaningful Career


Imagine this scene. You go to a networking event for social enterprise professionals. You don’t work in the space, but are keen to make a transition into it. You begin talking with someone at the event. You say, “Hi, I’m a financial analyst and want to get into impact investing. I think my strong financial modeling background could really add value to impact investors.” They look at you quizzically and then begin to ask you questions. “Why impact investing? Do you have an MBA? Are you sure impact investors need people with modeling experience?” You’re no longer networking, you’re being interrogated!

Sound familiar? Many of the professionals who I work with have a version of this story. They have great skills. They have the best of intentions. They want a more meaningful career. But, they seem to always come up with dead ends rather than opportunities when networking.

When working with these professionals, I often refer to Simon Sinek’s TED Talk Start with Why. If you haven’t seen it, watch it. Sinek explains how leaders and organizations can communicate what they do more effectively by starting with why they do it. “People don’t buy what they do, they buy why you do it.”

I won’t dig into how you reframe your communication to start with “why” in this blog. Sinek does a much better job of explaining it than I can. But, I do want to share why I think this concept is so important for navigating a more meaningful career in social enterprises and nonprofits.

Clarifying Your Goals

We begin our search for more meaningful work because the standard forms of compensation don’t resonate with us. We want something more than a paycheck and benefits. But defining what exactly we are looking for is hard. Starting with “why” will force you to articulate what really matters to you in your work. This powerful insight will help you convey what opportunities you’re looking for and evaluate the opportunities that show up.

Aligning with Mission

Organizations that are driven by a greater purpose want to know that you are as well. It’s not enough for them that you’re a great functional fit for a role. These organizations want to know that you are passionate about the mission of the organization. Starting with why is a great way to articulate that.

Soliciting Support

In the scene I mentioned above, imagine that you approached the networking event differently. Instead of starting with what you do and your interest in impact investing, you say,

“Hi, I believe that the decisions we make with our money can have a tremendous impact on our world. What really excites me is how tools like impact investing are maximizing the social and financial return of the money we invest. I’m currently a financial analyst and understand how powerful this shift in mindset can be. Do you have an ideas for how I might get involved in impact investing?”

My bet is that you would get much more helpful ideas and resources with this approach than if you led with your role and interest area. When you start with why, people tend to help you explore that deeply held belief rather than assess how qualified you are to pursue your specific interest.   

Use Simon Sinek’s talk to start crafting your own “why” statement for the work that interests you. If you need help applying this to your job search, I’m happy to help. Just leave a comment or send me a note.

Are you betting against your career in social enterprise?

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If you’re like me, you’re probably doing too much. You’ve been saying “yes” to all kinds of projects and now you’re loaded with commitments. Some of these projects might be advancing your pursuit of a more meaningful career, but others are just interesting opportunities. You’re “diversifying yourself” and “creating serendipity.” I tell myself this type of thing all the time. The problem is that when you’re driving toward a big goal (like finding a job or launching a company), side projects can quickly turn into betting against yourself.

When I launched Mission Driven six months ago, I took on a couple short-term contracts. These were meant to support me financially while I got Mission Driven off the ground. A means to an end. But I started building a reputation for the work that I was doing on the side and these short-term contracts turned into longer-term commitments. Last month, I spent more time on contract work than Mission Driven.

 It’s not that I would rather work on these contracts. They’re just safer and easier to execute on. I began to see a viable career alternative to running a company just in case Mission Driven doesn’t work out. And, without even realizing it, my short-term contracts turned into bets against myself. And the more I bet against myself, the more likely Mission Driven was to fail.   

I see people betting against themselves in the same way when pursuing more meaningful careers in social enterprise. They explore exciting opportunities while also maintaining a set of safe alternatives. Sometimes you have bills to pay and have to go for the easier money. I totally get that. But, don’t let these necessities hijack your goals. It is safer to diversify what you do. But careers, businesses, and life is not about doing what’s safe. It’s about finding what lights you up and then pouring yourself into that thing.

Finding Meaningful Work Means Finding Great Organizations

If I asked you, “What is the best part about your job right now?”, what would you say? Maybe it’s your team or flexibility of your work. Maybe it’s the opportunity to tackle new challenges or the positive impact your work has on the world. I’m guessing it’s not the specific functional tasks that you complete day-to-day. And yet, that’s exactly how we search for new jobs.

When looking for more meaningful work, it’s important to get clear on what actually matters to us and how to find it among new job opportunities. Typically, that means starting your search with...

Set Your Intention for Meaningful Work

etting career goals can be challenging. When I lead activities that ask professionals like you to map out what they want in the future, some grasp the concept immediately. However, others become paralyzed with the idea of coming up with the “right” answer.So instead of defining what we want to achieve in the future, what if we start by defining what would simply make today great?