Let’s talk about self-sabotage

Hadassah Damien
13 min readAug 4, 2023


Friends, we need to talk about some dysfunction and ideological traps we see in some activist, movement, and politically left-leaning communities.

We hope people use these observations and our ideas to have a better life and have more energy for things that matter. In fact, skip to the end to do some exercises to do just that!

But first, who “we” are: two radical lefty coaches:

  • Hadassah Damien a design strategist and facilitator for teams, and financial coach for queers, punks, and other people who feel left out of normy systems
  • Pippi Kessler, an organizational psychologist who does leadership and career coaching with activists, CEOs, Rabbis, artists, and educators.

We call ourselves Lefties because at our hearts we hate suffering, others as well as our own, and want to see a world where all people experience safety, well-being, equity, and fun. Hadassah has pursued that goal through talking to people about money and the design of systems, and Pippi through talking to people about their leadership and their careers.

What we’ve seen: In both of our work, we’ve seen a pattern that has worried us: people who we work with making choices that make them less and less healthy and happy over time, even though their espoused values (and often political work) are all about making a world that gets better and better for everyone. Why not also for them?

We often see activists count themselves out of the wellbeing that they are seeking for everyone else and framing their unhappiness as proof that they are community-focused, principled, and committed to ethics — or as proof that there is literally nothing they can do to change any aspect of their lives.

We love systemic analysis

We don’t believe that any person can willy-nilly change any part of their lives at will or that when activists describe feelings of powerlessness, it’s just an attitude problem.

It is true that there are systems of oppression and marginalization at play, full stop. It is also true that these systems impact some people more than others. Systems are at play in literally every facet of our lives, and taking a systemic view can help us make wise and informed decisions and help us understand what is happening to us.


Over-focusing on systemic analysis can have side effects

However, we notice some of our friends and clients — and, at times, ourselves! — being so upset about the existence of systems of oppression and marginalization that it makes it harder to try to change our personal life experiences within those systems.

Behaviors we’ve noticed:

  • Avoidance / refusing to self-sully / acting as if there is a gold star for never being near a “bad” thing. For example, in Hadassah’s work, she’ll often talk to clients who don’t have any plan for retirement because they are proud not to have contaminated themselves by interacting with the stock market. Pippi will often talk with leaders who don’t have any methods in place for feedback or performance reviews because they don’t want to be associated with “hierarchy” or evaluating someone else.
  • Ignoring / not thinking about it / Punting fixing problems to “after the revolution.” Some of Hadassah’s clients won’t save money because they believe that there will be a complete collapse of capitalism in the near term. Some of Pippi’s clients won’t ask themselves about their long-term goals because they feel that soon enough they won’t matter.
  • Othering change / not connecting you having an improved life with the justice we seek for all. Pippi will often talk to activists who are proud of how much they hate their apartments, partners, lunchboxes, or jobs. It can feel like proof of selflessness, or proof of the seriousness of oppression’s power, to valorize giving everything to the movement and not to lose time on frivolous things like dealing with your relationship issues or brainstorming a new career path. Hadassah frequently hears from people who are excited to donate money to others but are avoiding digging into a job change or savings habits that would help them have a less financially precarious life.
  • Focusing on what should not be true instead of what could get shifted or changed — focusing on the “should.” Pippi often works with clients on the gap between “what’s right” and “what’s real.” If you hate your boss, it can feel temporarily good to enumerate all the reasons why a boss shouldn’t act like that. But if your boss is acting like that, the question that will generate more motion in your life is a different question: “If I accept that this is the truth of what’s happening, what do I want to do?” In Hadassah’s work, this can take the form of clients having a lot of comfort talking about what’s wrong about capitalism, and a lot of discomfort talking about what they want their personal plan to be for surviving in it.
  • Being afraid to change due to being unsure of your identity if it’s not centered on subjugated experiences. Caucus spaces — identity-based groups gathered for purpose of ending oppression — are helpful formats we can use to share experiences and support one another. It’s often important to have spaces where people can take a break from cisgender people, white people, wealthy people, etc. Sometimes, though, we see another dynamic: a history on the Left of booting out people from belonging when they are seen as getting too close to power. Our past is littered with stories of bisexual women kicked out of their lesbian collective house for dating a man, or people seen as no longer trustworthy if they leave the neighborhood where they grew up or get more money. Knowing about these stories can bring up a lot of fear for people that if their life gets better, their relationships might get worse. Pippi’s parents, who lived in a van painted with psychedelic flamingos, eventually had to get a regular car when they had a third baby and couldn’t fit a third car seat. Her mom described the loss and dread she felt that if she made that choice, she was losing her fundamental identity as a countercultural weirdo. Spoiler alert: she is still a countercultural weirdo, and so are you even if you are able to get a better job or decide to get married. Hadassah has so many clients — and her own lived experience — who struggle with the transition of first wanting to have middle-class money, and then experiencing life differently once they have it. Some people avoid taking steps towards having enough money just because there’s a familiar solidarity in the struggle of not-enough. Let’s be clear: letting go of avoiding power is different from the true work of needing to accept and face that we have more power when we change class status. You will have ethical responsibilities if you get more power, but you also will still be you, in all of your complexity.

The outcome of these behaviors are simple: life continues to suck for a lot of people on the left, the line is blurred between things that can’t be changed and things that actually could, people who are working against oppression get burned out, and meanwhile folks who don’t care about justice hoard more resources and centralize more power.

This is our message of liberation and love — we want you to live

Both of us work with clients and organizations from a generative place, seeking to help people gain stability, capacity, and heart. It is in this vein we encourage people to take actions to improve their lives. To not give up. To not be bowed over by hopelessness or enormity. To not wallow in the desperation put upon us.

We both desperately want to see activists, movements, and people experiencing marginalization thrive. Because these are communities and experiences we too are rooted in.

We don’t believe in blaming people who are backed into a corner for being backed in there. We don’t believe that everyone can easily have everything if they just try harder. But what we do believe is that if something that’s bad in your life could wiggle and move, we want you to try to wiggle and move it as soon as you can, because we want you to live.

We urge you to balance systemic analysis with actively trying to live a life that does not suck

Our dream for activists is that all people who care about a world that’s good for everyone includes themselves in that vision. In both of our work, a message we spend a lot of time on is that your suffering doesn’t end oppression — the end of oppression, like oppression itself, is a systems game.

The important thing here is to ~balance~ analysis with action. We’re not saying to give into the shallow grave of navelgazing consumerism but we are saying don’t construct your whole identity around what should not be happening.

We’re not saying don’t acknowledge trauma and systems that create mass trauma; We’re saying, ask yourself: “What has to be true for me to both function and thrive in this traumatizing world?”

Let’s set the record straight: trying to make things a little better/less painful *for yourself* is NOT the same as approving of how things are!

New age manifesting ladies act like there’s a binary between caring about what you want in your life and caring about the bigger community but we don’t agree. Fixing the world is not in tension with fixing your own life. Fixing yourself is PART OF fixing the world. Doing the part you can is key.

A lot of what happens in the world is controlled disproportionately by centers of power: the CEOs who shape the economy, the politicians discussing over lunch decisions that shape our lives.

Your steps to incrementally move to get your head above water, save enough money to take a trip to see your friend, switch jobs to one you like better, or break up with your boyfriend you don’t like are never the deciding decision that changes everything for everyone else. You are not the flapping of the butterfly’s wings that completely changes the end of the movie. But you do have that kind of influence in your own life, in your family, in your friend group, and in your town.

Making changes in the areas you control does change everything — for your own life. Your life is meaningful.

Stop saying your life doesn’t matter but then acting like it’ll wreck things for others for you to be doing well. Neither is true.

Pro tip: your individual choice isn’t the hinge of the whole thing.

You are part of the world you seek to improve.

One critical step is to be ok with taking action that is intended to personally benefit you, by believing that you are as deserving of a good and nice life, as anyone else. The codependence of only being willing to improve your life because it also benefits “the community” or other people stands out. It’s ok to want to have a life that does not suck. It’s ok to work towards this

Having an ok life is not in tension with wanting oppression to end: you get to have both

If you have the leverage to end oppression with your personal choices, you better fucking do it. But most of the time, most of the people we work with aren’t ending oppression with their personal suffering — they’re just suffering. Plus: choosing suffering has a disparate impact on people based on their experiences, needs, and socioeconomic backgrounds.

So now what? Move beyond problems-as-identity to fight the real enemy

We both celebrate getting through struggle, and we want you to center success after and outside of the struggle. We too both had to learn how to understand ourselves aside from our oppressions. We want that for you.

Why — we want more people to be healthy, happy, and safe enough to be in a place to take on the right and create / live in a world that feels better.


Here’s two exercises, one from each of us, that we use with clients who are ready to make changes, by focusing on what we can control, in an oppressive world.

Damien: Cake-sized actions

It sure can feel overwhelming to try to make a change. Especially if the change’s outcome must be Ending Pain for All Other Humans.

You and I both know that’s not a feasible outcome for most things we might do, and yet it’s sometimes the standard we are holding ourselves to. What can change if you make your ideas more bite size and shrink what you are trying to do?

This is the purpose of the cake-sized actions exercise. Whether you’re thinking about an outcome or impact you want to make, or a concept you want to try, these prompts ask you to think about what you might do, sized relative to when in your life you might have one of these three kinds of cake:

  1. Think about a version of this that is the size of a Life Celebration or Wedding cake. Something you can expect to encounter once to a very few times over a lifetime. It takes years and years to build up to. It’s epic. It takes lots of people and resources.
  2. Next, think about a version of this that is the size of a birthday cake. It takes at most one year. It is special, but it recurs, and you can change it every year if you want.
  3. Finally, think about a cupcake size version of your idea. Something you could whip up on a random weeknight. Something that is doable by you or you and a pal or two. A manageable size and shape concept. One in which you feel safe to experiment with because it’s not that deep, you can try it again next week if you want. Liberating Structures calls this a 15% solution, and asks “What is your 15 percent? Where do you have discretion and freedom to act? What can you do without more resources or authority?”

Focus on your cupcake idea. What can you implement, start, change, or stop today? What small thing would nudge you closer to an outcome or help you play with an idea?

Pippi: “What Do I Control?” circle chart

One of the ways that oppressive systems make it hard to think is that the scale of the problems are so big that it can feel pointless to problem solve. One trick that you can try to help your brain focus on what you control is to simply ask yourself, “What do I control right now?” For some people, just asking the question points a lighted arrow in the direction of the next right step.

If it helps you to see a visual, you can also try making a simple chart.

How to do the exercise:

  • Draw 3 concentric circles like I did in the picture above (or download that picture to fill in).
  • In the center circle, write the things that you control the most right now
  • In the next ring, brainstorm what you have some control over, but not total control.
  • In the next ring, brainstorm what you only have a little control over.
  • Outside the circle, write things that you don’t control.
  • If you notice you’re getting overwhelmed, look at the purple circle to get ideas about what to focus on.
  • Damien’s computer background has a venn diagram — one side says, “Things you can control,” and the other side says, “Things that matter.” If you’re having trouble choosing between actions from what you brainstorms in the “things I control the most” circle, narrow it down by asking, “Of what I control, what matters the most to me and to my community?”

For example, let’s say you’re working at a job you hate but because of a combination of life factors, economic factors, and your identities, it would be really tough at that moment to get another job. Your chart might look like this:

Looking at your job in this format doesn’t fix everything and it doesn’t end systemic oppression. But it can help your mind stay oriented about what buttons you can push on the machine and how fast moving the effect of each button might be.

Now what?

People — take action! For YOU — your life. We’re not saying manifest, we’re just saying: let your self imagine a life you want, and move forward on making it more likely. Get little bits of joy, stability, and care. Don’t grind yourself without giving yourself life.

If you want more of our thoughts, check out our video, and to work with either of us:



Hadassah Damien

design strategist & facilitator // economics researcher @rffearlessmoney // progressive technologist // performer