The Challenges of Breaking into Social Enterprise


“What are the biggest challenges to getting into the social enterprise space?” A workshop participant asked me this great question last Tuesday and, to be honest, it took me a little off-guard.  I’ve worked with hundreds of professionals looking to break into social enterprise over the years, and I spend most of my time thinking in terms of opportunities, not challenges. But, it’s worth going into a social enterprise job search understanding the challenges you might face. So, I want to share a couple commons challenges to breaking into the social enterprise space.

Fragmentation in the Space

Unlike the traditional business, nonprofit, and government sectors, the social enterprise space is poorly mapped out. It’s a growing, entrepreneurial sector which means organizations come and go often, and senior leaders are typically too busy to promote their organization or convene in an industry group. Because of this, most social enterprises are relatively unknown and not well connected to their sector. So, when it comes to hiring, senior managers typically turn to the networks that are immediately around them.

This fragmentation is why building your own network in social enterprise is so important when looking for a job. Like everything else, hiring managers are looking for a quick and convenient hiring solution. You want to be top-of-mind for them when they start looking for their next hire, and the best way to do that is to get connected and stay connected with them.

Role Translation

Because social enterprise blends the nonprofit, for-profit, and government sectors together, job titles are highly inconsistent from one organization to the next. For example, business-minded teams will hire for operations roles, whereas nonprofit-minded teams are more likely to hire for program roles. They’re probably very similar positions, but hiring managers and job candidates alike get hung up on the wording. Never have semantics gotten in the way of so many opportunities.

Don’t get caught up in the game of appealing to every type of role you might be a fit for. I encourage you to focus on finding organizations that you would love to work for instead. Once you have identified a few, explore where your skills fit into that organization. Make them aware that you are interested in those opportunities and find ways to demonstrate your abilities. This makes you an obvious choice for the next open opportunity. These organizations can also be a great referral network to other opportunities that fit with your interests.

Navigating the social enterprise space on your own can be a challenging process. That’s why Mission Driven has developed the Break into Social Enterprise career accelerator. If you’re interested in joining, please reach out. The deadline to enroll is October 25!

What You Can Bring to a Meaningful Career

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For people who want a meaningful career, workplace culture is important. We all want to work in a place that is supportive, empowering, and aligned with our lifestyles. It’s important that the next organization we work for embodies the workplace culture we want. But how do you decide if an organization’s culture is right for you? 

Assessing culture is hard. You can collect a few anecdotes from people who work there and compare that with how the organization talks about itself. But that’s a lot of work for a pretty incomplete picture of that organization’s culture. We need a more direct approach.

When exploring the culture and values of organizations with Mission Driven participants, I’ve started to reframe the question from, “what do you want an organization’s culture to be like?” to “What do you want to bring to an organization’s culture?”

You create your own reality

This simple reframe puts you in control of your own experience. You have the freedom and agency to create a work environment that aligns with the life you want to lead. You can be excited about the challenges you get to solve. You can bring fun and energy to your meetings. You can create space for your team to bond. Start by defining the culture you want to create around you.

Will you fit in?

Now that you understand what culture you want to create, it’s time to assess how that will fit into a potential organization. This is much easier to assess than trying to uncover the culture of an organization. Instead of asking about work-life balance, you can say, “I like to get in early, get things done, and then get out while the sun’s still up so I can enjoy a bit of time outside. Do you think I’ll have the opportunity to do that here?”

We all want to be part of a great workplace culture. But, it’s very hard to find great culture if you’re not willing help create it. Get clear about what you want to bring to an organization and you’ll start finding organizations that would love to have you.

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.