Learning How to Lose

Ivy HestHow-To, Individual Sustainability, Supervising and Mentoring

I don't know who this woman is, but I feel like she's speaking to me.

I don’t know who this woman is, but I feel like she’s speaking to me.

Tuesday was election day, and the end of my first cycle in electoral politics.  Many of you know that I worked for a State Senate candidate since March, have been helping with the Democratic Committee in the area since April, and in October took on Field Director positions for two City Council campaigns.  It was a lot to handle at once, and I’ve learned my lesson there.  I can maybe do two, but only if the roles I play are distinctly different from each other, and don’t both require all my nights and weekends.

The official results are still being tallied, but my State Senate candidate won about 70% of the vote according to initial results!  It was very exciting to be a part of the campaign from early on, and get to know my candidate more over time in the different roles I’ve played.  We had a very intense, brutal primary, and once we broke through that, it was mostly smooth sailing form June through Tuesday.  Unfortunately, I keep forgetting about that victory, and only keep focusing on my losses— the two City Council races.

The results actually went exactly how I had expected them to, and I prepared my candidates for those results as well.  I tried to strike the balance between remaining hopeful and pushing them to keep going, and softening the fall if that’s what happens.  

It still doesn’t make losing any easier. 

And sometimes we lose.  Sometimes we do a lot right, and it still doesn’t work out.  We can speak truth to power and get a resounding NO in response.  Our campaigns come to a big climax with hundreds of people at a hearing, as our bill gets passed over without us even realizing it.  Sometimes we plan big fundraisers, get a lot of confirmations, and then it rains and no one shows up.  And sometimes we mess up.  We have theories of what ruined it, and we pore over it again and again, thinking of what we could have done differently, blaming ourselves and/or others.

I want to share with you some things I learned from this election.  Because reflection is so, so important, and I need to reflect on what happened. 

*I tend to hate what I feel are cheesy, broad statements…like the ones in the list below.  I always want a tangible lesson to come from it.   These do feel tangible to me, because I understand what it means when I do the opposite.  I hope they can serve as concrete support for you too.


Believe in your cause. I’ve asked myself a few times, “If I do the work and I get paid for it, does it really matter?”  The answer, for me, is always yes.  It matters.  I had the privilege of working with candidates who are actually effective AND genuine.  Whenever anyone asked me about my candidate for the Primary, my response was “well, he’s the least worst in this race, which is all that really matters.”  However, I am leaving the General Election feeling very proud and fortunate to have somehow landed a job with these people.  It makes the long hours and hard work have a purpose.  I truly believe he will make a great Senator.

Stay true to your own style.  This was the first time that I managed staff.  I had to fire the second person I hired.  I had to give warnings, and put my foot down.  But I also had a blast, and had some folks come back for more after the Primary.  We played music during phone banking, we threw paper airplanes with messages at each other, used fake names, and stood up to make an announcement every time something ridiculous happened.  If there were technical issues or a lot of “NO” responses in a row, I would stop everyone and have a dance party for a song, then put them back to work.  We had a great “YES” rate, 70%.  If I had done things the way all the books and websites told me to, I would have run a much tighter ship, and we all would have suffered for it.  I was unconventional, but effective as their manager.

Trust your gut.  You have no idea how many times I said, out loud, “Something’s wrong.  Something is definitely wrong,” but would keep quiet because I assumed someone knew better than me.  This happened with numbers that everyone insisted were true but I knew couldn’t be or candidates telling me “That’s not what everyone else told me to do”.  If I had trusted myself, I would have been able to fix a major data issue that affected multiple campaigns before it was an issue.  Several times when I assumed I didn’t know enough, the outcome could have been better had I spoken up.  

Advocate for your needs.  I asked all campaigns to pay me hourly, instead of salary.  I knew that electoral campaigns require a lot of hours, and I wanted to make sure that if I worked more hours, I got paid for that work. When we got closer to the election, I spent free time I had helping out other campaigns.  And when I finished early, I went home to take a nap.  I ate lots of McDonalds’ and subsisted solely on soda, and I would need to find a way to take better care of myself physically if I were to continue this work.  


Train your people.  When I managed the phone banks, I held a 30 minute training before every shift.  It was interactive and we role played, and there were times I didn’t know what to do with them so I explained the political climate or asked for their feedback on the script; but every day, without fail, I trained them.  When I would substitute for other campaigns or work with walkers who had never been trained, I would see the difference in how the volunteers or workers would feel after their time and what the results of their time were.  It’s all about the training.

Believe in yourself.  It was just a few weeks ago that my boss gave me the pep talk.  I’d been delaying decisions or ideas because “I’ve never done this before”, and he was tired of it.  “Ivy.  You may not have done exactly this scenario before.  But you’ve worked on and won many campaigns before.  You’ve trained people on doing this.  So.  Shut up and do the work the way you know how to do it.”  I still need to work on that, but he’s right.  I’ve done “this” many times before, just with a few variables switched around.  If I trusted myself and took more risks, I’d have learned more and we would have seen bigger results.

I learned so much from these campaigns, and I am grateful for those opportunities.  I hope that when I’m getting ready to start my next campaign, I can go back to this and remember how things were, and how they could be.  If I hadn’t done this, I might have made the same mistakes again.  There’s no guarantee I won’t still mess up, but I hope these reflections help me grow.

When we lose, we still gain, if we give ourselves the space to reflect.

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