On Friday, I (finally) had my signed DD-214 in hand. On Tuesday, I announced that I was running for the US House of Representatives.

That was my life exactly four years ago.

If whiplash had a spokesperson, it was me. But for all intents and purposes, I felt fine. Sure, I was leaving a career that I loved, having served with honor for more than a decade. But I was doing something else that I was sure that I’d love and that I’d dreamt of since the first grade: entering the political arena to represent my neighbors in government. I hadn’t anticipated cutting it so close between leaving active duty and starting the campaign; that ended up being more of a function of the military personnel system taking a lot longer than anticipated.

I thought I knew what I was getting into. I had been a political junkie since I was a kid. I had majored in political science at Annapolis. Heck, I even took the Harvard Kennedy School course aptly named “How to Be a Politician.” I did my “rolodexing,” hired (mostly) top-notch campaign consultants, and had started calling friends and family to begin filling my fundraising war chest. Sure, I was looking down a competitive, three-way Democratic primary where I was viewed as an outsider. But I had the plans, knowledge, and belief that nobody was going to work harder than me on the campaign trail.

I knew that I could win.

But I did not win.

So what happened? What did I learn? And what can I share with others to help them go from outside the political machine to election day with the most success?

A few words up front: my experience, and therefore my bias in writing, is with a federal campaign. I was a full-time candidate, which means I did not have a job while I campaigned. While campaigning for non-federal office may be different, I believe the principles are the same, since you are trading the need to raise less money in, say, a campaign for the county legislature, but you also likely have a regular job that will take up most of your time.

What Happened

I love campaigning. Or rather, I should say, I love talking with people about how government works for them, and how it could work for them better.

I love helping people, and for me, the act of running for office was an exercise in making people feel seen and heard. I started the campaign by helping people in the coastal village of Fair Haven fill up and deliver sandbags to defend against historic flooding. I held a public town hall on gun violence just days after a young neighbor was killed by a gun, bringing together a grieving community. I brought my kids out to campaign for underdog candidates for county executive, county legislature, and city council.

I also love communicating about ideas. I relished every opportunity to take part in public forums with other candidates and community members to talk about policy, framing our agenda, and how we could reach people with our message. I tried to eschew the typical politician-speak that you hear from many candidates by being up-front, honest, and precise about policy and messaging.

And on the campaigning, people, and communicating fronts, I feel like we were successful. We developed loyal volunteers and even brought people to tears at our events. We routinely felt like we won the room at candidate forums, building momentum and interest in our campaign. And we raised nearly half a million dollars, won more than two dozen local endorsements, and hired a passionate staff of committed public servants – all in less than 9 months.

Still, we didn’t win. I ended the campaign a few months before the primary election, opting to salvage what little money and goodwill I still had rather than burning it all to the ground in an increasingly negative, three-way race. There were many reasons for this; it’s important to reflect on at least three of them here today.

What I Learned

First and foremost, you need to understand what kind of district you are running in because it will give you some ideas on what kind of campaign you need to run. I thought I understood the district: majority-rural, post-industrial, blue-collar with an aging population of reliable voters and a fierce, young core around a handful of universities.

And while that information is probably an accurate representation of New York’s old 24th Congressional District, it omits an important political fact: NY-24 was a “D+3” district according to the Cook Partisan Voter Index and was one of the Top 3-5 most competitive House seats in America. While Democrats enjoyed a voter enrollment advantage, this was a solidly “purple” district.

What does that mean for prospective candidates? For Democrats, there are really three types of districts: solidly “red” ones where a Democrat wins less than 5-10% of the time, solidly “blue” ones where a Democrat wins more than 90% of the time, and purple districts like NY-24 where party control splits regularly.

In red districts, Democrats frequently run as “sacrificial lambs,” if you’ll forgive the metaphor. Without much hope for victory, candidates often run and hope for their Republican opponent to make a colossal or disqualifying mistake. While there isn’t a great deal of support for these candidates in the General Election, they can serve to organize and motivate the local party infrastructure to show up and maybe win a surprise election once every few decades. Democrats win in red districts through significant cross-over voters, using persuasion and name recognition to outweigh the partisan priors of voters.

In blue districts, the real election is not in November; it is the Primary Election. In order to be on the ballot in November, Democrats must first defeat other Democrats in the primary. This can be tricky, but it is mostly a numbers game – excite and mobilize the most Democratic voters on Primary Day, and you are the winner. Candidates who raise a lot of money – and can therefore raise their name recognition through paid media – can be successful in blue districts, but big fundraising is not always a silver bullet here; upstart candidates with a better connection to reliable Democratic primary voters can win the ground game despite deep-pocketed opponents.

In purple districts, more often than not, it’s all about fundraising. These are competitive districts in November, and Democratic insiders are very attuned to a candidate’s fundraising totals because of what they think it means about a candidate’s chances of winning the General Election. Of course, Democrats who are outraised by Republicans in purple districts can – and often still do – win, because fundraising absent name recognition and a compelling, organizing campaign principle is pyrrhic fundraising. But a culture of “money over everything” persists in these Democratic circles and is the driving factor towards getting through a Democratic primary in a purple district.

So, while I raised about $500,000 during my campaign, my opponents raised about $100,000 more than me during that same time period. There are many reasons for this, and I’ve thought about them all often – time off for a new baby, not committing to an aggressive fundraising schedule, fewer political connections and favors to call in, etc – but they are, at the end of the day, simply excuses for the end result that I was third out of three candidates in overall fundraising.

Second, you must understand the political machinery wherever you are running. In some places, this is a handful of Democrats that get together regularly in the basement of a church. In other places, this is a well-oiled machine of block captains, bosses, and committee members who serve as party gatekeepers. This machine is often a shortcut for voter mobilization; if the local Democratic committee or prominent, well-known local Democrats support you, rank-and-file Democratic primary voters will take note. If you are running in a primary election, winning the preponderance of support from Democratic committee members is important.

Third, and finally, all of this shit is hard. The act of putting yourself out there is a highly vulnerable exercise and tying it to a campaign where people constantly weigh in on your worth in the form of money, time of day, and votes is exhausting. Maintaining the kind of fundraising schedule to be competitive in a purple district is bordering on insanity. Add a family or outside job to the mix? It’s certifiable.

What to Do Different

I’ve discussed the three biggest things I learned on the campaign trail: money, machines, and madness. While I maintain that it is difficult to learn these lessons without first being a candidate yourself, here are three practices you can put into place now if you are thinking about running for office soon.

First and foremost, develop a mental health plan. This is the most important aspect of running for office. Yes, you need money. Yes, you need votes. But if you don’t have a solid handle on your mental and physical health when you start, you are going to have a much more difficult time raising money and garnering votes.

Second, if you’re in a purple district, commit to an aggressive fundraising schedule. By “aggressive,” I mean at least 60-80 hours per week at the start of your campaign for federal candidates. This might seem unnatural – it certainly did for me! – but the money you raise early on will enable you to do the things that you love later in the campaign with less stress, i.e. talking with people, developing connections, and persuading voters.

Finally, learn the rules of the game early. If you’re in a purple district, there are likely significant party gatekeepers to the process of running for office; unfortunately, these folks can be proxies for hundreds or even thousands of primary voters. Like it or not, most of these people do not care where you served, how you served, or how good your ideas are; they care about what you will do for them and how your candidacy will enhance their own power or prospects. Money talks and memory lingers; candidates who can cut big checks to committees or elected officials can more easily show their value than the rest of us, and those who can point to wealthy or powerful family members with connections to the local committee or elected establishment have a much easier time, too. Yes, this is absolutely disgusting, but as one particularly pernicious party insider once told me: “that’s just how it is around here.”

Why This is All Pretty Fucked Up

If you don’t come from money or a politically connected family, the harsh reality is that you are going to have to work many times harder than other, more privileged candidates to attain recognition or achieve success on the campaign trail. Privilege in elected politics is vicious; entire “legacies” are erected upon it and the good-paying, taxpayer funded salaries it ensures. There is a reason that power corrupts and that many of the most powerful politicians in your local area are likely the descendants of some other powerful politician.

During my campaign, I thought I did a pretty good job as a candidate – raising decent money, showing up for other people, and articulating a Democratic message that could win a General Election against a popular and entrenched incumbent. But I am under no illusions that I was the best candidate in my congressional district. The more I traveled and talked and connected, the more I saw of the thousands of volunteers, workers, and leaders in our communities who probably should be representing us in public office: the parents, advocates, and kind-hearted souls who do the lion’s share of the work ministering to people in various, essential aspects of life.

But these people don’t run for office, often because the very lessons learned I have laid out here preclude them from running altogether. They cannot afford to be a full-time candidate. They cannot afford to keep their kids in childcare for the entire day. They cannot afford the mental and physical toll that campaigns in our current, post-Citizens United era take on honest human beings.

And yet our country needs these people to represent us in government. We need people in government who serve others before themselves and who are less concerned with legacy than they are about policy. We need people in government who will work like hell to change the very system of running for political office I have described here so that it can be easier and less costly for more of the right kinds of people to run in the future.

So the biggest lesson that I learned from running for office so soon after leaving the military is that I do not, in fact, need to run for office to make this country better. If I can make the process of running for office more accessible, more understandable, and more successful for more of the right people? That’s the real win.