How NOT to Solve Homelessness

Uncategorized Sep 10, 2025

Earlier this year I posed the following on LinkedIn:

"What is our sector-wide strategy for ending homelessness in the United States? If you had to summarize it in a sentence, what would you say it is? And if you can't describe it or don't think there is one, I'd sincerely appreciate your sharing that too."

This question and its follow-up post were viewed over 12,000 times, generating some really fantastic - and generally consistent - feedback about the state of our movement:

#1 - There is no sector-wide strategy. 

  • This is the big one. After 15 years on the frontlines of this crisis, it is hard to admit, but I think that's an accurate assessment.

#2 - We have a lot of "plans," but plans aren't necessarily strategies. 

  • If I follow a map that leads in the wrong destination, does it matter how well I navigate it?

#3 - It feels like "Housing First" used to be a unifying strategy (or at least a unifying mantra), but maybe it's not anymore?

  • There's something very valuable to unpack here around what happens when we take a specific intervention (i.e., a methodology for helping people experiencing chronic homelessness get into and maintain permanent supportive housing), we expand it to more of a philosophy without any real quality controls, and then that term gets co-opted against us (see next).

#4 - To whatever extent our strategy requires buy-in from elected officials and the public, we don’t really have it. 

  • At all levels of government - federal, state and local - the trend is increasingly shifting to enforcement and criminalization.

#5 - Ensuring we have sufficient funding and resources seems like a key, unifying goal.

  • However, very few communities can actually articulate a clear business plan for what they need. 

#6 - Certain emerging initiatives seem to be getting a lot of attention, such as the need for more prevention.

  • But isn't this a little bit of a pattern for us, shifting from promising practice to promising practice? It was Housing First for a while, then By-Name-Lists, then new forms of emergency shelter, and now prevention. Don't effective systems of care need all of these components working together at the same time? 

#7 - Finally, there's an ongoing tension over what we’re actually responsible for.

  • Should we be focusing our efforts on the best possible "emergency" response to our nation's housing crisis (i.e., ending people's literal homelessness as quickly as possible) and/or should we be focusing on addressing the underlying socioeconomic issues creating that emergency in the first place (e.g., the cost of housing, access to behavioral healthcare)?

As I've reflected on these insights over the last six months, what I find really interesting is that rather than telling us where to go, all of these perspectives seem to be pointing towards what NOT to do as a sector. 

There is something really helpful in leaning into that ... 

 

How NOT to Solve a Problem

I believe there is immense value in looking at sectors and industries other than our own to gain different perspectives on how we can be more effective. 

Consider financial services. 

Many of us have heard the name Warren Buffett. 

The CEO and Chairman of Berkshire Hathaway.

The “Oracle of Omaha.”

Buffett is currently worth ~ $150 billion dollars, regularly making him one of the wealthiest people on the planet.

Fewer people might know the name Charlie Munger.

Munger was the Vice Chairman of Berkshire Hathaway and Warren Buffett’s self-described “closest partner and right-hand man.” He passed away in late 2023.

One of the keys to Buffett and Munger’s success has been the development of powerful “heuristics,” which are principles and frameworks that have helped them approach complex problems, such as where to invest their (and their customers’) money.

One of their most famous frameworks is inversion. 

As human beings, we have a tendency to plan forward.

We come up with a vision for where we want to go, and then we develop strategies and tactics for getting there.

One of Munger’s tried and true approaches to problem solving was to do the opposite. In the simplest possible terms, we must:

“Invert, always invert.”

This insight to plan backwards was born out of hard-earned, real world experience.

During World War II, Munger worked as a meteorologist drawing weather maps to clear pilots for takeoff. 

Rather than tackling this question head on, he approached it in reverse, asking instead:

"Suppose I want to kill a lot of pilots. What would be the easiest way to do it?"

He came to two conclusions:

  1. Get planes into cold temperatures that would cause them to ice up and crash, or
  2. Get pilots into areas where they would run out of fuel before they could safely land.

Thus, Munger’s strategy became avoiding these two scenarios at all costs.

Later applying this framework to the stock market and financial investment, Buffett and Munger shaped Berkshire Hathaway's strategy around principles such as:

  • Don’t invest in businesses you don’t understand. If you can’t explain it in a few sentences, walk away.

  • Don’t rely on promises without proof. If the results aren’t already showing up in real life (i.e., cash flowing businesses), don’t bet on them.

  • Don’t chase fads or glamour stocks. Hype and trends fade, but sound economics persist and grow.

  • Don’t confuse a great story with a great deal. A wonderful company can still be a terrible investment if the price is too high.

  • Don’t partner with poor managers. Even the best business model fails under the wrong leadership.

Perhaps most importantly of all though, they have been laser-focused on NOT unnecessarily disrupting the power of compound returns.

Here is an absolutely crazy statistic - upwards of 99% of Warren Buffett's current wealth was generated AFTER his 65th birthday. 

How is that possible?

Between 1965 and 2024, the stock market grew, on average, 10% per year.

Therefore, by simply staying in the market, by sticking to a core strategic aim through all of the inevitable ups and downs of the business cycle, compounding growth became an unstoppable engine for long-term wealth creation. 

To put hard numbers to this, if you invested $100 in the S&P 500 in 1965 and simply left it alone:

  • After 1 year you would have $110 ... 
  • After 2 years you would have $121 ...
  • After 30 years you would $1,745 ... 
  • And after 50 years you would have $11,739 ...

 

How NOT to Solve Homelessness

Since the emergence of modern homelessness roughly 45 years ago, this is easily the lowest moment in the history of our response. 

This might seem like a strange and counterintuitive reaction, but I think there is actually a real freedom and liberation to this reality.  

Why?

There's nothing else to be afraid of.

All of the horrifying things we feared might happen are already coming to pass. 

So if we - the homeless service sector - already have a bad reputation, and we have not effectively persuaded the people who need to be persuaded that our course of action is the best one, then why not just be honest and own up to what isn't working and actually come up with a better strategy?

And channeling the wisdom of inversion, why not approach this grand challenge in reverse? In other words, what if we started asking ourselves:

"How, as a movement, are we guaranteed to NEVER solve homelessness in the United States?"

A list of what NOT to do would certainly include things like:

#1 - Fragmenting the response.

  • If every state, county, CoC, city, and provider is free to do their own thing, how can we ever create an aligned strategy and movement? 

#2 - Working in silos. 

  • When organizations reinvent the wheel and fail to learn from others, time, energy, and resources are wasted, and our systems become more confusing in the process.

#3 - Defending the status quo. 

  • Do we hold ourselves accountable to the benchmarks set by peers, or when others make progress, do we justify why "things are different here"?

#4 - Ignoring the power holders.

  • Is our strategy aimed at rallying the people who already agree with us or persuading the civic leaders with real power and resources?

#5 - Neglecting the public. 

  • Do we tell community members they are ignorant and inhumane, or do we proactively find ways to align our values and focus areas with their concerns?

#6 - Measuring the wrong things.

  • If the speed of rehousing and housing retention aren’t core metrics, efforts drift into activities that look busy but don’t prioritize solving the real problem.

#7 - Speaking different languages.

  • Do we rebrand our interventions and use inconsistent terminology and jargon, thus complicating coordination and evaluation efforts?

#8 - Complicating the costs.

  • Do we keep asking for more and more resources without creating logical and coherent business plans unpacking our actual expenses and resource needs? 

#9 - Not incorporating customer feedback.

  • Do we meaningfully incorporate feedback from people using our systems and make real changes, or do we tokenize their involvement to check a box? 

#10 - Continually changing the approach. 

  • Is our movement shaped by an unwavering compass and strategy, or do we swing our efforts reactively from initiative to new initiative, from plan to new plan?

Similar to the power of compounding financial returns, I think this last point carries the most weight for our sector too. 

At the end of the day, there are really just two levers for reducing homelessness - decreasing inflow (i.e., the number of people becoming homeless) and increasing outflow (i.e., the number of people exiting homelessness).

Let's say a community starts with:

  • 1,000 people on their Point-in-Time Count
  • 1,000 people flowing into their system every year
  • 1,000 people flowing out of their system every year

In other words, they are at exact equilibrium - their numbers aren't getting worse nor are they getting better. 

If this community simply focused on trying to slow inflow by 2% every year while also increasing outflow by 2% every year, they'd see the following:

  • End of Year 1 ... Inflow = 980 ... Outflow = 1,020 ... PIT = 960
  • End of Year 2 ... Inflow = 960 ... Outflow = 1,040 ... PIT = 880
  • End of Year 3 ... Inflow = 941 ... Outflow = 1,061 ... PIT = 760
  • End of Year 4 ... Inflow = 922 ... Outflow = 1,082 ... PIT = 600
  • End of Year 5 ... Inflow = 904 ... Outflow = 1,104 ... PIT = 400

With nothing more than 2% annual improvement, within just 5 years, this simple compounding process would lead to a 60% reduction in overall homelessness. 

And how does that kind of slow, consistent, accelerating momentum happen?

By doing the opposite of everything above ... 

 

Please Help Spread the Word

If there are practitioners, leaders, and homelessness Change Makers who you think should be reading this blog, I would be deeply grateful if you would consider sharing this and encouraging them to subscribe. 

Thank you so much for your partnership! 

- Andrew

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