win by losing

TEP #042: Changemakers Unintentionally Supporting the Status Quo? Oh No!

Today, I’m going to tell you about the weirdest, most ironic discovery I’ve made while working in the social sector for the last 20 years:

Many so-called changemakers help maintain the status quo more than they create change.

They think they’re leading the charge.

Like doing whatever it takes to get another grant.

Or, rallying to save a struggling nonprofit.

But actually, their fear of failure virtually guarantees they’ll do everything in their power to put a positive spin on current change efforts, promising or not.

The strangest part?

They’re not even aware of their role in keeping things the same.

Sometimes I imagine coming back in 20 years and finding them still slogging away…but nothing is different.

In this week’s issue, I’m going to show you how so many changemakers unintentionally reinforce the status quo through 3 real-world examples.

Then, I’m going to give you a counterintuitive strategy and 7 tips to avoid this all-too-common trap.

Let’s dive in.

Who is against change?

I’ve led change initiatives for nonprofits, state government and philanthropy.

In each case, the greatest foes to affecting major change weren’t our obvious opponents.

Opponents were straight-forward and would argue their side. 

Oftentimes, we enjoyed verbally sparring with them and trying to convince those on the fence about whose argument was better.

It was a contentious but fair competition.

The much bigger threats to doing things differently were long-time changemakers who professed to be on our side but simultaneously clung to the status quo.

They would publicly praise our efforts, saying they shared our goals for change, but behind the scenes they would work against us.

Giving the same grants as in the last 5 years.

Employing the same strategy that wasn’t making an impact.

It was the same old leaders opposing any new approach.

It sounds like I’m suggesting there was and is a conspiracy against doing anything new.

That’s not exactly right.

It’s more like there is so much bureaucratic and institutional momentum that it’s easier to continue doing the same things – as long as it’s not obvious they are a total failure – rather than try anything really innovative.

Because something truly innovative can totally fail.

And then who is blamed?

Doing the same things, even if not truly impactful, is safer.

Here are 3 common examples I’ve seen again and again in the social sector.

Example #1: Continuing a multi-year grant that isn’t working

Changemakers who receive grants to implement social initiatives may feel a strong sense of responsibility to demonstrate results and maintain the funder’s confidence. 

As a result, they may persist with a grant-funded project even when it becomes evident that the project is not achieving the intended impact. 

The fear of admitting failure or losing future funding can drive them to continue with ineffective efforts, ultimately reinforcing the status quo of inefficient resource allocation.

Example #2: Promoting a systems change initiative that isn’t creating any real changes

Changemakers working on complex systems change initiatives face considerable challenges, including resistance from powerful stakeholders and bureaucratic barriers. 

Despite their best efforts, some initiatives may encounter roadblocks that hinder progress. 

In the face of these challenges, changemakers may be tempted to continue pushing forward, hoping for a breakthrough, rather than admitting that the current approach is not succeeding.

This can inadvertently reinforce the status quo by supporting ineffective leaders and  perpetuating ineffective strategies.

Example #3: Always rescuing struggling nonprofits

Nonprofits play a crucial role in addressing social issues. 

However, some nonprofits may struggle to achieve their intended impact due to various reasons, such as inadequate funding, misalignment with community needs, or limited capacity. 

Changemakers within these struggling nonprofits may be emotionally attached to their organization’s mission and reluctant to consider the possibility of failure. 

The fear of negative consequences, including potential harm to beneficiaries or loss of community support, can lead them to persist with unsustainable efforts, reinforcing the status quo of limited impact.

An alternative: Winning by losing

Here’s something totally different.

Rather than winning every battle but losing the war for transformative change, embrace losing.

Because sometimes, failing is the best way to win.

Stop that useless grant.

Give up on a failing initiative.

Let the struggling organization die.

Let’s call it winning by losing.

By letting things fail, you create space for something new. 

It’s a concept that emphasizes the importance of adaptability, resilience, and a willingness to learn from failure. 

Rather than stubbornly persisting with ineffective efforts and arguments, you abandon them in favor of exploring alternative strategies. 

By doing so, you create opportunities for growth and improvement, which can ultimately lead to transformative change in the long run.

Embrace a learning culture and iterative approach

To avoid status quo traps, and accept losing when appropriate, adopt the following 7 approaches:

  • Normalize Failure: Foster a culture that views failure as a valuable learning experience rather than a mark of incompetence. Encourage open discussions about failures and share the lessons learned with stakeholders.
  • Monitor and Evaluate: Implement rigorous monitoring and evaluation practices to regularly assess the effectiveness of initiatives. Use data-driven insights to make informed decisions about whether to continue, pivot, or stop a particular effort.
  • Embrace Iteration: Recognize that the path to success may involve multiple iterations and adjustments. Be flexible and willing to adapt strategies based on feedback and evidence.
  • Prioritize Impact: Keep the focus on the ultimate impact and outcomes rather than preserving the status quo or avoiding potential short-term setbacks.
  • Encourage Innovation: Create an environment that encourages innovation and experimentation. Support changemakers in testing new ideas and taking calculated risks.
  • Build Support Networks: Collaborate with other stakeholders, organizations, and experts to build support networks that can provide valuable insights and help overcome challenges.
  • Share Knowledge: Share successes and failures transparently with the broader social sector community. Learning from one another’s experiences can accelerate progress and prevent the duplication of unsuccessful efforts.


If you can accept being wrong and failing in the short-term, you’ll increase your chances for meaningful and sustainable impact over the long-term.

See you next week.


Whenever you’re ready, there are two ways I can help you:

I’m a strategic advisor for the toughest societal problems like poverty, crime and homelessness. People come to me when they want to stop spinning their wheels and get transformative, systems-level change.

I’m a coach for emerging and executive leaders in the social and public sectors who want to make progress on their biggest goals and challenges.

Let’s find out how I can help you become transformational.