Have a Nice Life: a Career Change Survival Guide

 Have a Nice Life is a podcast miniseries + workbook on career changing, from career coach and organizational psychologist Pippi Kessler, and me, a money coach and business strategist.

As two lefty queers who’ve both taken convoluted and uncertain paths to good work and stability, we realized through conversations over the last year that a lot of our clients [and friends!] struggle to figure out how to do things that work for them with their lives and to have enough money to feel like they are thriving … and we had some strong opinions and answers about why and how to help.


The people we know specifically struggle with systemic barriers like experiences of racial and/or gender marginalization and/or ableism, wage gaps, lack of role models, trauma, unfriendliness to neurodiversity, aversion to capitalism and everything related … plus all the everyday reasons people struggle with this stuff, like new jobs few people have heard of in emerging technologies, underfunding of public sector work, and the difficulty of the tasks of finding work and understanding if it’ll cover your financial needs.

At the same time, the struggle and despair of not having work that fits your brain, skills, or financial needs can not be understated. Most of us don’t get to pick IF we work or not, but we do get some say in WHAT we do and the field it’s in, which has impact on how much we’re paid.

I always want to send people to Pippi, but her coaching books out and vice verse for me; plus it’s not cheap or financially accessible to everyone to work with a coach one on one in the first place. We decided to pool our brains and make a little workbook. We tested it with some readers [thank you to our partners Ariel Federow and Jules Skloot and other readers Bethan Polentz and Justin Rosen Smolen] and in a workshop, and decided to expand it to be not-so-little.


The workbook details eight steps to figure out what you want from a job and work at this moment in your life, and prompts you to consider your needs and values, to expand what you know about jobs, and gives you a blueprint to make mini-decisions and run some life experiments so you can decide safely. No manifestation or encouragement to jump without a net here!

It has stories, visuals, resources, and detailed exercise instructions, if you like that kind of thing. It’s 115 pages [!!] and you’ll get it as a digital download PDF.

Have a Nice Life Career Change Survival Guide

Most career advice ignores realities of trauma, systemic oppression, and assumes you’re clear on your dream job. Not this time!

Welcome to your anticapitalist survival guide to finding work that works for you, having enough money, and balancing your values and goals with the world we're in.

Learn to redesign your work and financial life without having to know the future, despair, hate your life, or love wage labor. 

This workbook was co-written by Hadassah Damien, money coach and business strategist, and Pippi Kessler, career coach and organizational psychologist. 

If you prefer to listen to the workbook instead of read it, you can hear selections from all the chapters in our free Have a Nice Life podcast.




Finally, we wanted to get the content out people more accessibly than just in a workbook, so we are recording a serial podcast that covers the workbook’s key points. This series will run from March 20 – May 7 [or longer if we decide to get wild]. It’ll cover who we are and why we’re doing this, the systemic barriers at play, and gives you exercises that build on each other.

Listen to it on Spotify here, Apple Podcasts, or listen and grab the RSS on Acast here.


The frameworks in Have a Nice Life do not require you to already know what you want to do or love the reality of wage labor in the first place, but it does require you to be ready to enter a phase of facing the challenges of untangling what you want and what’s possible. We created exercises to help you mentally get into that moment and be safer while there, but we know it’s also a decision that can take time to get to.

Also, our series will NOT cover how to find jobs to apply for, interview, write a resume, or get hired. Other people have great content on that stuff, go find them once you have a sense of what you want to do. That’s what we can help with: the what, and why it fits YOU.

Feedback is welcomed! I hope it helps you figure out how to fit your work, job, and money together, better.