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When ‘Success’ is Messy, Unpredictable, and Full of Moving Parts

Updated: Sep 22, 2020

In today’s environment, no matter our sector or role, change is the only thing we can be certain of.

What does this mean for the hard work of pushing through seemingly intractable social problems? There are two questions I ask all the time, both of myself and of the people and organizations I consult for.

  1. How can we exhibit and encourage open minds and creativity in revisioning programs and solutions?

  2. How can we be ready to change course quickly and effectively, while maintaining laser-sharp clarity around mission?

There is such urgency for our goals! It can be hard to slow down and be strategic

We have so much pressure to show ‘impact’ that we sometimes don’t want to see tensions that derail trust and relationships. How do we step back and ensure that the conditions for success are there? Since everything affects everything, we've got to harness our intentions and be strategic, rather than reactive.

Goals, Roles, Tools & Souls

Goals, Roles, Tools & Souls. My shorthand for the information necessary to answer questions 1 and 2, above, and to know whether or not the conditions for success are in place.

Goals: Do we know where and why we are doing the work? What is the change that we want to see? Does it lead to justice, equity, and healing in the communities we seek to serve?

Roles: Who’s doing what? It’s very hard to steer the ship if “who’s supposed to be where” and “who is responsible for that” is unclear. Spontaneity and giving people the flexibility to vary their roles between projects is important, but each time we set out with a project or strategy we need to assign roles, and carefully consider talents and interests in those assignments.

Tools: We all view problems through a different lens. That’s why we need to agree on tools that can help us dig deeper. What data are we using? How are we collecting it? How are we defining success? Are our processes and methods the right ones to advance our goals?

Souls: Is our work fueled by passion and authenticity? Is our organization guided by those who have the most at stake in our stated social change efforts, or, are we trying to “do for” the community?

Paradigm Shifts: When a New World View is Needed

How can anyone build anything when the very foundation is shifting underneath? Organizations and individuals are equally confronted with this question. It’s hard to see new ways of working when we are inside our unique organizations, doing what we do every day. ‘Founder’s Syndrome’ is one familiar example of how ‘keeping on keeping on’ impacts both the person and the organization. It’s great to be able to do everything, until suddenly doing everything means everything is stuck, waiting for your approval. Gaining strength and flexibility for an athlete isn’t a one-off activity. It takes months. It’s one thing to see what needs to change, but actually getting new ways of day to day work into everybody’s muscles needs to be built into processes and procedures. Deciding to become an organizational bodybuilder can feel like a luxury when you’ve never been one (and have multiple, major responsibilities). So what needs to change? What can change?

Let’s look at a real-life example of a collaborative response to one of those “intractable social problems,” and strategic approaches to some of the organizational challenges that arose.

A Case Study: Opportunity Youth Employment

Working within New York City’s complex human service systems for nearly three decades, I am constantly reminded of the pitfalls of hypothetical approaches to big problems. Since moving to Staten Island a few years ago, I’ve had the privilege to work and live alongside neighbors and colleagues where there’s little patience for jargon. The current reality on Staten Island’s North Shore (closest to Manhattan and the ferry) is that the borough’s most economically and racially/ethnically diverse communities are in the eye of developers, and deeply vulnerable to displacement from gentrification. Gentrification displaces low-income families without necessarily producing job opportunities that the younger generation can access. According to a 2017 report by NYC’s Comptroller:

“Despite rapid business growth in lower income neighborhoods, many residents in these communities remain disconnected from the labor market. This is particularly true among young people, many of whom are both Out-of-School and Out-of-Work (OSOW). While employment and education outcomes have significantly improved for the city’s youth, large geographic and racial disparities persist...well over a fifth of 18-24 years olds in lower income neighborhoods were OSOW in 2015. This compares to just 13.5 percent in higher income areas.”

On Staten Island, 18% of young adults between the ages of 18 and 25—and 24% of North Shore residents— are neither in school nor working.

The Theory of Change

There are a number of reasons for barriers to entry to workforce for high-needs populations. The strengths that are required for survival mean that for many OSOW young adults, also known as Opportunity Youth, just getting to a training or employment program requires overcoming obstacles that take more effort than is available in a 24-hour day. Their experience in programs and schools may have included all kinds of messages throwing doubt on their ability to succeed. So, they may be suspicious, angry, insecure or simply unaware that they have gifts and skills employers want and need. The real lack of support some of these young people deal with is often not fully understood. Attitudes may also be influenced by unconscious bias and racism. Despite the fact that most people try and fail at early jobs, workforce development programs and prospective employers may feel and say “this kid is not motivated or serious about working. They stopped showing up; they’re not taking advantage of the opportunities they’re being given.”

A Need for Collaboration: Youth WINS

In response to the ongoing unemployment crisis among Staten Island’s low-income young adults, The Staten Island Foundation (the borough’s principle grantmaking philanthropy), called on JobsFirstNYC, a neutral intermediary and champion for the workforce needs of out-of-school, out-of-work young adults in New York City, to help catalyze a collaborative, community-based strategy for systemic change. The goal was successful education and employment pathways leading to economic sustainability for young adults on Staten Island, and the collaboration of people and organizations tasked with making that happen became Youth WINS.

“Collaborative”: Defining and Clarifying

Youth WINS is not an organization in itself, nor is it a funder. It’s a collective of stakeholders (non-profit organizations, funders, businesses, government) who have made a commitment to tackle Staten Island’s young adult employment problems by joining forces. Every participant gives time and resources to this common cause.

Collective Impact

As communities all over the world grapple with urgent systems change, a rich network of knowledge and resources is emerging and growing. The Collective Impact model, an approach codified by the consulting firm FSG, emphasizes 5 conditions that together produce alignment and lead to results:

“...a common agenda, shared measurement systems, mutually reinforcing activities, continuous communication, and backbone support organizations.”

There has been criticism that rigid alignment to the Collective Impact model can overshadow the knowledge and expertise within the communities with the most at stake, and can replicate systems of oppression. I believe it is vital to approach any tool with a critical perspective, name the pitfalls, and adapt approaches to ensure that the vision of equity and justice is driving the efforts. Tools must be used, not blindly followed. Otherwise, we run the risk of a building that won’t stand, on top of a foundation that can’t hold.

Embracing Change to Strengthen the Collaborative

I first began to work with Youth WINS as a community stakeholder, and was honored when the leadership asked if I would submit a proposal to become a consultant to the Steering Committee. My first few months were about listening to the stakeholders and leaders on the committee, and being a strategic partner to the executive leadership. Being available for thought and discussion over a substantial period had many positive results.

A common tension in collaborative initiatives is that strong leaders are used to getting things done. So, when people aren't sure of their roles and don't know where to plug in, their efforts to be helpful can backfire. A few members may seem to be doing everything, and resentment can grow (just like in family systems--think of chores!). Ultimately, there’s a weakening in the connective tissue needed to sustain any successful initiative.

At Youth WINS, because we spent time building trust and creating space for deep exploration of such common pitfalls, the executive leadership was able to rewire patterns to ultimately unleash greater initiative among the membership.

Intensive, Relentless Engagement Required

As unemployment rates improve, many OSOW or Opportunity Youth young adults will find opportunities in the improved economy. But, the most high-needs youth among them will be left behind unless they have access to intensive support services to address complex barriers such as homelessness, criminal justice involvement, foster care, immigration issues, disabilities, mental health, trauma, and much more. This is why Youth WINS requires a strategic, collaborative mindset from all involved.


A young man we’ll call “Damian” was homeless, moving between couch-surfing with friends, staying in drop-in shelters, and sleeping in the ferry terminal. He wanted to enter a culinary training program that could potentially lead to a life-sustaining income. But, the program required ID, which he didn’t have because he’d been mugged, months previously. His birth certificate was with his mother, but she was in another state and they never spoke. He hoped to get ID through the ID NYC program (which takes into account complicated life situations like homelessness) but it was still overwhelming on his own. A Youth WINS team member was able to gain his trust and work with him through 3 full weeks as he talked to his mother.

For young adults like Damian what’s essential is a place to hang out, a place to feel seen and heard before and after appointments and program meetings. Staff frequently give of their own time and resources, trying to meet emotional and social needs simultaneously with helping youth launch into employment. Today, Damian is on track to start his program. But his chances of slipping off the radar are high. He needs the ongoing net of support provided by the people who are Youth WINS. And they, in turn, need organizational support and personal resiliency to keep helping Damian and his peers navigate their very slippery slopes.

What Equals ‘Success’?

Back to the underlying principles and ongoing questions of Goals, Roles, Tools and Souls. I’ve learned to reframe success as 1. staying engaged in the process and 2. constantly taking stock, while keeping our eyes on the prize.

Collective Impact and community-based initiatives require trust, trust to say “I don’t know,” trust to guard against jargon or the latest fads, trust to accept mutual accountability between disparate partners. We’ve got to remember that fast-spinning wheels generate sparks, but sparks burn out quickly. I’ve realized that my most successful consulting experiences have meant acting as a trusted sounding board and mirror, helping everyone involved see the forest and the trees. This is hard, messy and iterative work that takes time, usually longer than everyone wants it to.

Finally, for myself I’ve learned that if my work doesn’t challenge me, my soul isn’t in it. And we, all of us, your peers, your organization, your partner organizations and, most of all, the populations you want to make a difference with, need your soul.

Thousands of humans, known as the "Castellers de Barcelona," intricately balance on top of one another to form a human tower
"Castellers de Barcelona" form a human tower (Gustau Nacarino, Reuters)


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