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From city to startup: Reflections on a career change

Updated: Sep 8, 2020

In 2017, after 18 years working in the non-profit sector and municipal government, I shifted into the world of startups and started a whole new phase of my education. Here are five things I learned.

1. The startup world: the best of the best, and the worst of the worst.

I love the startup world! But not all of it. The elements that get the most attention and investment – the stop-at-nothing competitiveness, the agnostic pivoting until someone gives you money – are worshipped to a fault. They reinforce and reward self-promotion and general sh***iness, and are at least part of the reason that investment has tended to favor a certain type of person who can talk a good game, but who may or may not be good at delivering outcomes. Furthermore, there are not enough people in the startup world asking if the outcomes you’re delivering are positive or negative. We’re seeing now, in our deeply polarized society, that failing to think through the end game of brilliant tech innovations can have terrible, unanticipated repercussions. We know you can make money doing this. Should you?

But there’s another side. The side that I gravitate to, and that I found after some committed searching, is the side that emphasizes collaboration and partnership, the “rising tides lift all boats” mentality, the side that aims for diversity and inclusion and in doing so also does incredible things. This side of the startup world is just as present and just as important, but it doesn’t make the headlines in the way that Mark Zuckerberg or Elon Musk or Steve Jobs or Travis Kalanick or Martin Shkreli or Jeff Bezos do.*

I like collaboration, positivity, and positive impact. Those qualities drew me to the sustainability field in local government, and they’re what draw me to the organizations and people I work with as an entrepreneur.

2. Government gets a bad rap. Sometimes it deserves it. Sometimes it doesn’t.

Talk about the government in mixed company and prepare yourself for a collective eye roll. As someone whose post-city-employee interactions with local government have involved dealing with a surly development plan reviewer and responding to a weed complaint filed by a grumpy neighbor, I get it. For many people this is what interactions with government are: Annoying. Inexplicably cumbersome.

But what I saw in my experience in local government was the incredible people working to make it better – the innovators, the intrapreneurs. The people who saw how it could be better and who believed in a fundamental way in a government of ideals, a government that is focused on serving constituents and communities and making the world a better place.

These people exist elsewhere too. But there’s something special about the people who believe so strongly that we can build a better world from the ground up, who are almost inevitably not getting paid what they’re worth, who are willing to wade through the frustrations of bureaucracy and true public transparency because they know that this is what it takes to positively change their communities. That’s a lesson in dedication the startup sector can learn from.

3. Ready. Fire. Aim.

There’s something to Mark Zuckerberg’s “move fast and break things” philosophy. Tech increasingly makes it possible, sometimes dangerously so. Not sure how people are going to react to something? Throw it out there. Test it. Tweak it. Throw it out there again. Test multiple ideas at once, see what sticks.

Government, of course, is not great at this, although sometimes it tries to be and I think it’s getting better. Testing ideas often…usually…requires several layers of approvals. The processes are public. Scrutiny is high, and missteps can be uncomfortable, or create problems for elected officials. There’s just not a lot of wiggle room. But the benefits of a more experiment-based approach could be immense.

4. It’s okay to lie.

To figure out what’s going to work as a startup, you have to engage in a little game of pretend, just to see if people will actually click the button or do whatever it is you want them to do, even if the tool or the service is nowhere near being an actual thing. This happens everywhere – in all kinds of digital ads, on social media, on websites. Companies are constantly testing consumers to see what they respond to.

For someone who spent years trying not to be the city employee who ended up on the front page of the local paper for doing or saying something stupid, this approach feels a lot like lying.

The alternative to pretending, of course, is to spend a ton of money making the thing, and then to unveil it (“TA-DA!”), only to learn that nobody wants it. Which is what government often does, for exactly the reasons mentioned above. Putting half-baked ideas into the world can result in negative public attention, and that’s a hard sell to elected officials and political-appointee supervisors, even though in the long run it might mean fewer tax dollars spent to achieve better outcomes.

5. Talking to people is important

Government is really good at talking to people in very specific contexts, and that context often involves checking off requirements, not getting truly meaningful feedback or acting on that feedback.

(This image borrowed from Talking to Humans)

To make #3 and #4 above actually result in things that work (and as a startup, things that will make money), I had to really learn (and am still learning) how to talk to people. Not talk to the people who show up (often the same small group…most city employees could name their core crew of public meeting regulars. Are you still out there, Gabe and Bruce and David?), or meet public input requirements in the most minimal way, or share a fully fleshed-out idea at a point when there’s little opportunity to change it. This involves backing up, asking people about their lives, what problems they wish they could solve, enabling the intended target audience to drive the process instead.

Early on in my startup journey I was introduced to Talking to Humans. It’s simple and has pictures and you should absolutely read it. I wish I’d found it years ago.


People in the startup world may never understand how much I loved my city government job. I loved an aspirational view of what local government could be and do, and aimed every day to achieve that ideal. My former colleagues in cities everywhere continue to aspire to do the same, with a clear focus on making their communities better.

These change makers share a lot with the startup world in terms of their willingness to innovate and approach things differently. How do we better enable these two sectors to talk to each other?


*These are all dudes. Just stating a fact.

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