Should I run for office?

Five questions to ask yourself before taking the plunge.

This country was in a dark place during the early months of the Trump administration, but as spring has bloomed, so has resistance to Trump’s most unpopular policies - in the streets, in the courts, and maybe even in the halls of Congress. Trump 1 prompted an unprecedented number of fresh faces running for office, and the pattern seems to be repeating. I ran for Manhattan District Attorney last cycle, and as someone who came into that race with almost two decades of activist and political experience, I thought I’d know my way around a candidacy. It turns out that being a candidate is psychologically quite different from even seemingly similar experiences like running an issue campaign or staffing an electoral candidate.

Being a candidate is an all-consuming venture that takes over your life and the lives of the people around you. That’s why any first-time candidate should have a gameplan before they launch. Start with five questions to ask yourself before running for office.

• Would I be good at the job?

• Is this the most effective way I can bring change?

• Is someone else better-suited for the change I seek also running?

• Can I raise the money?

• Who is really going to stand with me?

1. Would I be good at the job?

The simplest, threshold questions, the one you’ll spend the next year or two answering over and over and over again: Why are you qualified to hold this position, and what will you do with it if you win? It’s amazing how many first-time candidates (or, unfortunately, people who have run unsuccessfully multiple times) are unable to string together how their own lived and professional experiences give them the expertise to do the job, and connect that to what they would do differently than the incumbent or their other opponents. My partner Cristina, a political media strategist, has a great exercise that gets new candidates to think about what uniquely qualifies them for the office they seek, and does it early in the process: credentials, constituents and contrast. What vision are you offering constituents? What within your bio tells those constituents that you could make that vision a reality? How does that contrast you from the other folks in the field? Too many candidates think that just because an incumbent sucks, by dint of being someone different, they deserve support.

There are steps you can take by yourself well before your semi-public “exploratory” phase, like identifying who is effective at the job you’re pursuing, or assessing what skills you have that you think can translate to being an elected official. Most popular elected officials are compelling storytellers and bridge-builders, and know their communities' issues inside and out. People successfully running executive offices or agencies have poise under constant pressure and know how to effectively delegate and empower. Does this sound like you?

We are living through a period of anti-incumbent fever, particularly as Democrats, and it’s well-deserved. But that doesn’t mean we can replace one set of incompetent leaders with another, or we’ll be running in place forever. Years before I ran for Manhattan DA, I had considered a race in Brooklyn, where I was living. One night I got off at the wrong bus stop and was completely turned around, even with my cell phone. That’s when I realized that my lack of deep familiarity with the neighborhood, would preclude me from being a great elected official, even though I had other things going for me. That is a correctable defect, and if it were my dream to represent that community, I could have spent the next few years focusing on curing it. But life had other plans, which leads to our second question.

2. Is this the most effective way I can bring change?

Let’s start with why you are running. Is it to fix a problem? What if I could wave a wand and solve it - would you still feel the need to run? That’s a quick way to figure out if this race is about issues facing our communities or about you. Running for office takes one to two years, sometimes longer with laying the groundwork, and then you’re a newly elected official learning the ropes. If you put all that time, money, and energy towards the problem, would that get you where you wanted faster than you being elected to the City Council or State Assembly?

Personally, I’ve always felt most drawn to run for office when I’ve been least excited about the work I’m already doing. Soon after I passed on said Brooklyn race, I began managing the #CLOSErikers campaign, which remains one of the most impactful and meaningful experiences of my life. Our team completely shifted city policy in a few years, even though virtually no elected officials were with us when we started - arguably more impactful than anything I could have done as a local elected. My interest in running for office waned considerably as I criss-crossed the country setting up dynamic criminal justice campaigns for the ACLU. Sitting here now, I have little interest in running for office because of the work I’m doing, passing legislation in different states and taking on major issues in Congress.

All of that said, there’s a reason running for office has such a hold on people who believe in making change: It’s the most visible way to do it. The political press loves covering politicians; they spend far less time on the organizing campaigns that make change possible. They might cover an impactful court case, but they’ll spend more time on the Supreme Court and how it affects Trump than they will the lawyers working tirelessly on it. With the visibility comes glamor, which is seductive to extraverted people, and the power, which is seductive to most people.

3. Can I raise the money?

Money is not the most important thing, it’s the only thing. Having worked in the legal and policy arena on campaign finance reform post-Citizens United, I was perfectly aware that money mattered in political campaigns, but was still somehow naive about its importance. “How’s fundraising going?” is to political call time what “So, what do you do?” is to cocktail parties.

You will not be taken seriously by the political class if you don’t raise money, ideally more money than anyone else in the race, including the incumbent. Money is the measure of how seriously you are being taken by political stakeholders, even to unions, socialists, grassroots activists, and other people who vow to take on big money in their politics. I hate that this is true.

The number of donors would at least be a fairer way to measure popular support, but nope, it’s the main dollar amount, which will always be driven by big checks. The way you’ll get those is by calling people, for two to three hours per day, suffering blistering rejection rates. This is literally every first-time candidate’s least favorite part about running for office, and it continues forever until you’ve effectively ensconced yourself in a seat without competition or are about to retire.

If you’re an organizer considering running, you might be thinking, “who needs the money when you’ve got the people?” But even the best organizers have low name recognition with the voting public, and reaching them requires money in the form of mailers, digital ads, and in many races, paid TV. There are very few examples of first-time candidates doing well, let alone winning, without significant fundraising hauls. There’s no shortcut here.

Literally the only good news about raising money for political races: You can figure out if you have the stomach for it before embarrassing yourself publicly. You can ask 100 people close to you to donate to your campaign account before you “launch.” If even that doesn’t yield a favorable reception and decent dollars, spare yourself and pass on running.

4. Is someone else better-suited for the change I seek also running?

Challengers must start with a clear explanation of why they would better serve the community than the incumbent. In a quarter-century of being around elections, it baffles me how rarely I can get a challenger to concisely or meaningfully answer this. The same question extends to what differentiates you from the other contestants in an open race.

The best legislators I know bring a combination of lived and professional experience to the role - they are both able to connect with and understand the challenges people in the community face, but they have the skills and knowledge to do something about. If there is someone else running who has a more compelling story and/or more experience than you, there might still be an argument for why you are the better candidate, but you must be prepared to relentlessly make it.

Finally, people running for executive positions (Mayor, Governor, District Attorney) should have a demonstrated history of management and leadership. After a decade of building and leading modest-sized teams, it frustrates me to no end when political novices don’t consider that part of the job. Everyone who doesn’t have those skills gives the stock answers about “hiring smart people,” “listening to experts,” or “surrounding themselves with diverse voices.” But how many actually do that in their campaigns? For example, Barack Obama had virtually no executive experience, but his campaign was remarkably well-run. That was a good sign! If you are running for an executive office, be humble about that lack of experience, and have a plan to do something about it both during the campaign and after you’re elected.

The hardest thing about knowing whether you’re the best candidate for a race is that you have to decide based on incomplete information. A few years ago, a friend was running a spirited campaign challenging an incumbent. When a more well-known local politician realized there was an opportunity to unseat that incumbent, she jumped in the race and pushed my friend out. Being a first-mover earns you the cred to stay in a race that others only later see the wisdom of joining. But you also have to be realistic; once a new set of candidates have eroded your path to victory, there’s no point in staying in the race for the sake of it.

5. Who is really going to stand with me?

Running for office is incredibly lonely and isolating, which seems paradoxical, since you’re spending all day in contact with other people. Call time is a wrenchingly solitary experience, full of rejection; some candidates have volunteers with them taking notes just for the sake of company. Canvassing can be more uplifting, but we’ve all had rough days on the doors. No one knows exactly what you’re going through, except other candidates, which is why opponents can sometimes bond during a race, like I did with Alvin Bragg when we were running for Manhattan DA. You see them across the bar, drink in hand, waiting to pitch the same three dozen people you are at a political club at 9pm on a Tuesday.

Because it’s such an isolating experience, having people who will stand with you through thick or thin matters, and no matter how well-liked, rich, or professionally successful you are, that list is going to be smaller than you think. Is your romantic partner on board? Truly? Is your family going to be supportive? How many friends, with their own busy lives, can you count on to do more than the minimum? That’s your real base.

Last year a candidate with a lifetime of impressive experience was about to announce. He told me he had a plan for 100 people he knew closely to each bring in 100 donors - those 10,000 donors would give him the resources he needed to win the race. I knew that wouldn’t work, but couldn’t talk him down from it. He ended up with fewer than 2,000 donors - still impressive - but not nearly what he needed or expected. This is a very common first-time candidate experience.

Counter-intuitively, people you know through politics are even less reliable than those in your extended personal network. They like you, protest with you, work with you on legislation, and will give you a pound at a holiday party, but public support in a competitive race? Very different calculation. I was personally stunned at how many people who I had helped with their own political careers ultimately made the same calculation as a random union leader - starting with how much money I’d raised. As with so much of this list, the kind of personality who can cooly shake that off will do better than the kind who’ll take it personally.

Postgame: The act of running usually leaves first-time candidates with a feeling of duality, inspiration from all the people you get to meet in the course of running, paired with a deep cynicism about the political process. These five questions are meant to get the cynical part out of the way before you run.

If you or someone you know is thinking about running, share this article with them! Though in my experience, running for office is like law school - if someone asks you whether they should do it, they’re fishing for you to say yes.

We are living through politically unprecedented times in this country. If you are feeling called to serve, we need you to make an impact. Let’s just figure out the best way to do that.