Planning Your Career – With Jen O’Malley Dillon

Most organizers find and fall in love with organizing in part because they are ambitious—ambitious to promote their values, ambitious to change their community, ambitious to have an impact. Tucked in alongside these lofty goals is often an ambition for an impressive and far-reaching career in campaigns or politics. And that’s okay! Caring about what kind of future you will have and what kind of legacy you will leave does not diminish caring about making progress neighbor by neighbor.

When you are an organizer, you should be fully invested in the work in front of you. The only way you will succeed is by doing that. But, you can start (and probably already are!) to think about the next steps in your career, and you can take action to best prepare yourself for your future.

There isn’t one right way to do this, but there certainly are a few wrong ways. Schmoozing with and sucking up to the most senior person in the room isn’t how you will get ahead. Showing real results, real collaboration, real leadership, and real effort is.

Jen O’Malley Dillon has had a dream career—working hard all across the country on every type of race, serving on five presidential campaigns, leading some of the most groundbreaking movements in recent political history, and starting her own consulting firm. We asked her how she’s done it all and what priorities she has always remained focused on throughout her career.

Here is her advice for you as you think ahead about your career.

Don’t worry about the title you have— worry about the work you do instead.

“I actually spent a long time as a field director. I was a regional field director at the end of the Gore campaign, followed by being a field director on a mayor’s race, on a statewide senate race, on the Iowa caucus, and then on a runoff in Louisiana.

First of all, there’s probably never going to be a job I loved more than that. Second of all, I didn’t ever look at it like I wasn’t moving ahead and being promoted because I felt like each experience was a different challenge, a different place—a place that I didn’t know with people I didn’t know, and on different races—a caucus is very different than a mayor’s race, which is very different than a statewide race.”

If you work on a presidential race from early primary season all the way to election day, you will likely find yourself quickly getting promoted a couple of times. It can all seem so speedy and so awesome, but then… the new and fancier titles won’t come as quickly. But that’s not a bad thing!

Each and every campaign you work on is different and each will require different things of you. Worry more about the work you are doing, the challenges you will face, and the impact you will have on each race and less about what new title you have on your resume. Your future employers will do the same, I promise.

Think first about how you can build your experience and learn more.

“I was very focused on the experience— what I would learn, what I would be challenged by and what I liked to do. I remember when I got on the Obama campaign, we were sort of making up what my title was. To me, it’s about the work and it’s about making sure that I like it and that’s really important. The only way you do what we do and sacrifice what we sacrifice and can give what you have to give is, you have to like it. You have to like what you do— not every second of it, but most of it.”

Pursuing that which you enjoy will make you a better worker and a better organizer. The experience you have on each race is much more important than thinking about the stepping stones for a successful career. If you focus on the experience and not on perception, you will actually make yourself better.

Commit to staying out in the field for awhile.

“I stayed out [in the field] for a long time. Because the presidential was my first big race, afterwards many people went to D.C. I think that’s great and I went to D.C. for a few months as well, but then I went back out on the campaign trail. I started doing off-year races. I really wanted to try all different kinds of races to figure out what I liked best.

Because I stayed out for so long, I was able to get a little more experience than some other folks and that gave me a leg up when I was competing with other people for a job. While you’re young and have an interest and a hunger, I totally recommend to people that they should [stay out in the field for awhile.] I think maybe that isn’t as common as it used to be. At that time, it wasn’t that common either, but I think that helped give me a leg up.”

D.C. is an exciting place to be—especially if your candidate won. And there’s nothing wrong with pursuing work in D.C. after your first race. But if you really enjoy campaigning and field work and plan to join more campaigns soon, consider working on lower profile races during the off-years. Building up your experience in between big national elections will position you better for the future and will make you an even better organizer. (Which is what we’re all trying to do!)

Explore as much as possible.

“What you should be doing as an organizer is figuring out what you like, figuring out what you’re good at, and figuring out what paths will get you there. Use when you’re young as an opportunity to try on a lot of things for size.”

Organizing requires SO many different skills. In one week, you may give the field pitch at a huge rally, organize a house party at a supporter’s home, lead a volunteer training, develop a new system to get your team’s data entered quickly, recruit volunteers through email and twitter, manage a team meeting, talk to 150 voters and so much more. Each day you get to explore what you enjoy most and where your unique skillset aligns with your passions.

Don’t just assume one path is the right one for you. Explore tasks, skills, campaigns, organizations, and locations to find your special niche. Once you’ve found it, pursue it like crazy.

Do what you have fun doing.

“[Once] I was really struggling between being a field director on a statewide race (and I’d already been a field director before) or being a (first-time) campaign manager on a congressional race. Frankly, I don’t think either was a bad path or just one was the right path. I was weighing all of the options and honest to god, I was sitting in the bathtub rolled up in the fetal position trying to figure out what in the hell to do.

I called my dad and he said, ‘You are young. What is the thing that you think you’ll have the most fun doing?’ I had never thought of it that way. I was only thinking, ‘What would set me up best? Which one would I be sure I’d be ready for? What would people look at? What would be the best thing for me to get ahead?’ I kind of lost track of what would be fun. The right answer for me was to be the field director and I knew it the minute he said that.

Because I did that race—this was Tim Johnson’s race in South Dakota where we won by 524 votes — it charted the path for my career. I truly believe that. And I chose it because I thought it was going to be more fun. “

Don’t forget this crucial part of career planning. If you’re an organizer you are either young or young at heart— don’t waste your energy or squander time on something you won’t enjoy.

As Jen says, “Don’t take it so seriously. When you’re young, you don’t have to solve what the rest of your life’s going to look like in one decision. Give yourself the flexibility and the opportunity to figure out what’s right for you. Make sure you’re thinking about what’s fun and what you like to do, just as much as you think about other criteria. Because that’s really where the secret is in my career, and the secret of many of my friends who have done very well: it’s that they’ve chosen to be around fun people and smart people they can learn from. And that is far more important than whether you’re on the right campaign or have the right title.”
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