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When Putting Your Passion for Change into Practice Fails | Lessons on Starting a Nonprofit

A quote by Russ Finkelstein.

The theme of Russ Finkelstein's professional life? Helping others find fulfillment in their work.

As the Managing Director at Clearly Next, a company that helps people navigate their career, and a senior advisor to both the Talent Philanthropy Project and New Organizing Institute, nothing makes him happier than drawing out the potential of those around him. Saying he's "people-oriented" might be an understatement.

But it took him a failed attempt at starting a nonprofit to realize that when it comes to his own projects, input and support from others is essential.

After a long stint as the Associate Director here at Idealist in Portland, Oregon, he came up with the idea for a social enterprise called All Your Possibilities in 2010. He did everything right. He created an advisory board. Joined a social entrepreneurship fellowship. Acquired fiscal sponsorship.

Despite his best intentions, however, All Your Possibilities never took off. What Russ didn't take into account was how much he needed someone else to be at his side.

In our condensed and edited interview below, he talks about the lessons he learned from this journey - including the importance of knowing what makes you thrive, the need to be kinder to ourselves, and why sometimes walking away is the right thing to do.

What was the idea for All Your Possibilities?

I was hoping to create an online space where young people could find role models - people who were relatable to them in a multitude of ways and had gone on to achieve professional success.

The idea was that these individuals would share their stories, and youth could locate them based on how they perceived their identity, whether it was by geography, interests, professional aspirations, or other kinds of characteristics (race, ethnicity, size, handicap, etc.).

My next hope was to incorporate searchabillity so that these youth could find graduates of the high schools and colleges that they were attending.

How did you come up with the idea?


What happened pretty quickly was that I started hating the fact that I was working on my own.

[/pullquote]It's a thing I've thought about for a long time as someone who is gay and didn't necessarily feel like I had a role model growing up. Very often the folks who were gay and well-known were in celebrity culture and I had difficulty seeing how they were like me.

Things have changed somewhat generationally, but with the additional issue of suicide, I saw a real need to start giving LBGTQIA youth the inspiration that comes with seeing people like them who've succeeded. It’s hard to know how people see themselves and where they view themselves as most vulnerable. My hope was that with lots of tagging, young people could find someone who mirrored their experience as they saw it. And hopefully this would allow young people to begin to see what’s possible for them professionally.

What else about your background made you ready to start such a nonprofit?

What I heard, and have heard from many peers in the same situation, is that when you leave an organization people say, "You're going to do something amazing next." You have credibility based on prior accomplishments and anxiety based on how certain others seem to be.

I knew I had some credibility coming from Idealist and that I had to do something that was meaningful to me, something that really mattered and was going to have impact. And what I ultimately care about is helping people finding fulfilling work. Given the lack of attention paid to careers for LGBTQIA youth, it felt like a void worth filling.

One of the things that really struck me with the It Gets Better campaign was that it seemed to be missing a next step beyond a feeling that things will improve. It was more a series of quick commercials that wasn't necessarily hyper relatable to individuals nor offered them a path to making it better.

I was thinking more about how people could take a next step. I had been working on All Your Possibilities prior to It Gets Better, and it felt like it could fill in the void of giving young people more specific aspirations. It was the most important work I could do.

The funny thing is that I don't know if I necessarily ever was the best person. I wasn't someone who worked with the LGBTQIA community or with youth. But I thought I could make a credible case to many people, even though there were certain things in my background that would've made me stronger.

What was your first step in getting this off the ground?

The first step was having conversations with people and seeing if they thought this was something that could be useful. I spoke with twenty people who ran programs dedicated to LGBTQIA youth, I spoke with funders, and a convened a few working sessions with people who could possibly spec out and create a website.

The feedback was largely positive. So I started doing things to create some sort of structure. I pulled together an advisory board. I received fiscal sponsorship. I also ended up joining a fellowship through Portland State University to help incubate the concept.

How far did you get before you ran into challenges?

What happened pretty quickly was that I started hating the fact that I was working on my own.

I like working with people. I get in my head way too easily and I need to have someone to bounce ideas off of. Even with good friends and an interested advisory board I still felt largely alone and a bit paralyzed in the work.

At what point in the project had you realized this?

It's not about me being the person to do it, it's much more about it being done.

I was seeking an external sign that this was going to succeed. I made it to very near the end of the Echoing Green fellowship process and when that fell through, I wasn’t quite sure where to pivot. I figured that setting up structures was going to move me along in the process. However, even with these things in place, I realized how much I need someone else to work alongside. In part, that’s why I think I spend so much time helping others in start-up mode. I get the challenges and vulnerability far too well.

But the idea of finding someone to be a #2 felt impossible. The people I know who've had a concept and found someone they didn't know or know well to serve as a co-director had things dissolve quickly.

When you're not generating revenue and requiring someone to do this outside of their day job, it's hard to have faith that they are going to be as committed as you. Especially when thing get tough. And things are going to get tough.

How did you try and work through this isolation problem?

I have this notion/delusion that that if you work hard enough you can figure out any problem. But I was stuck and struggling to move ahead. I gave myself permission to say that now may not be the right time and I may come back to this later.

So you made the decision not to continue. What did you tell people, and what were their reactions?

What I often said to people was that I needed to take some time away, and that I learned about what conditions I need to be successful. I also learned to give myself permission at an earlier stage to walk away from something. The truth is that having been successful before means that people give you a bit more room to fail. Your track record helps. In truth though, it also can make you risk averse. You can become afraid to take public risks.

When you made the decision, did you have any doubts?

People often don’t realize how long a startup can take, and how easy it is to swallow up your life. I always have doubts and I still have doubts. I'm always going to be someone who has them. That's just the way I am in the world.

Hopefully now I'll be able to recognize my challenge earlier and not take something on that didn't allow me to have someone to work with from the start. My other hope is that if something else doesn't come along that's similar to All Your Possibilities, then there may be a time in the not-too-distant future when I can go back to it with different conditions and start again.

Would you ever give the idea away?

Yes. I've never been the person fixated on being in front. I'm way more interested in the work happening. Especially when it comes to stuff like this - we're talking about potentially saving lives and being an inspiration to people - that's what matters to me.

It's not about me being the person to do it, it's much more about it being done.

How did you transition from All Your Possibilities to the work you're doing now?

I had other work I was doing at the same time to pay my bills that was occurring at the same time. I needed to close what I was doing with All Your Possibilities - including speaking with the fiscal sponsors and my supporters and also dealing with feelings of guilt and failure. My friends and colleagues were great and supportive in my realizing this truth about how I prefer to work.

Finally, I had a conversation with Elliott, founder of Clearly Next, who had been having some challenges in moving ahead. We realized that we had a shared interest and a need to have a partner. From there we just got to work.

What advice do you have for someone who finds themselves in a similar situation?

People often don't realize how long a startup can take, and how easy it is to swallow up your life.

Going in, a lot of people are attracted to it because they want to be the public face of something or fill a personal void of some sort. They don't think about questions like: What are the metrics for success? Is it sustainably personally and financially? Is the organization my long-term commitment? What are the conditions to help me do my best work? And can I realize them? Those kinds of questions need a lot more research and reflection.

The big thing is to create markers to track success that you hit or miss. If you're not making some of them, either recognize this might be a sign that maybe this isn't the thing you should be doing or at least have the conversation about possibly stepping away with one or two people you really respect. Give yourself the opportunity to walk away instead of allowing it to drag on.

How can we all become more comfortable with the words "quit" and "failure"?

Think about it from this perspective: You had a friend work hard on something that was really meaningful. They did the research, and approached it in a serious and thoughtful way. Then they told you after some period of time, "I really made the effort but I realized for the following reasons it wasn't going to work out." You'd probably respond with, "Well, I think it's amazing you made the effort. There's never a guarantee of success, but it takes a great deal of courage to go out there and try. It's amazing you had the conviction to do it."

That's the response we most often have to other people. But the way we view ourselves tends to be much more purely focused on having failed. The more mindful we can be of that, the better.

Maybe it's just an issue even with the use of the word "failure." It's more about taking calculated risks. People tend to have issue if you're wildly doing things that have no context, or if you haven't done research or if you're throwing everything at something that's not grounded in the world.

There’s nothing wrong with failing at something if you were as informed as you could be and you learned something new about yourself.

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By Celeste Hamilton Dennis

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