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My work is both difficult and fun, and I don’t see that as a conflict: part of what makes things fun is that they are challenging — I enjoy a sense of “mastery” in my work, knowing that not everyone can do this, and often feeling that awesome “damn that was hard but I did it!” sense of satisfaction / exhilaration. I also have a great deal of autonomy in my work — that matters a LOT, and creativity is my every-day. I am not enormously well paid: I’m a University writing professor. But neither am I poor, and I get to work with young adults which is a reward in itself. Work can and should be “fun” — we are only human, mere mortals, we get one go-round in this world: it’s not to much to ask that we do something that is meaningful to us, where our skills matter, where our fellow humans appreciate us — that’s really all it takes for it to be fun.

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I spent a lot of time nannying/camp counselor-ing/Sunday School teaching/generally being around kids before I launched into my Real Career. One thing that a boss taught me has always stuck with me - which is that kids will have the most fun and feel the most free when they know there are constraints in place to protect them. I.e., camp counselors who will stop the game if it gets too rough, who will call them back if they're getting to close to a cliff, who will save them if they struggle in the water. If they're fearful that they're going to get hurt, that someone will be mean to them, that people will break the rules, they're unable to fully have fun and relax because they feel like they have to be on high alert.

I think about this a lot in relation to the work world. I felt very unable to have fun and actually celebrate my victories when I felt like my workload was unreasonable, I'd never get out from under it, my manager didn't have my back, I was worried I'd be fired for poor performance, I was constantly seeking approval and not getting it. Even when I finished something impressive, I felt like I couldn't get joy out of that because of the low levels of anxiety that just floated along with me from meeting to meeting, home and back again.

As a kid, there are adult figures who can help build safety nets around you so you can feel protected and nurtured. At this point, I think it's naïve to assume I'll have managers along the way who can do that work for me now. A good manager is hard to find, and I'm not going to spend my time holding my breath for one to stumble along. But I do spend a lot of time thinking about how I can chip away at that "high alert" feeling that keeps me from relaxing into my work. Did I really have to commit to getting that project done by Friday, or did my over achieving brain convince myself that asking for another week was totally unreasonable? Is everyone actually judging me for taking a full hour long lunch break outside, or did I invent the side eyes? Is it actually catastrophic if I don't know the answer to my coworker's question, or can I just say "I'm not sure!" and let them fend for themselves? My brain has a tendency to catastrophize, create anxiety where there is none, make fake rules and restrictions I have to follow, and convince myself I'm on the cusp of being fired if I'm not 110% excellent at my job, and that's honestly the biggest barrier between me and a chill job with a healthy dose of apathy and enjoyment. But 99% of those feelings are invented in my brain! I'm not about to get fired! That so rarely happens! Maybe the CEOs are able to have fun because they don't walk around on eggshells that someone will fire them if they sneeze wrong.

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"As a kid, there are adult figures who can help build safety nets around you so you can feel protected and nurtured. At this point, I think it's naïve to assume I'll have managers along the way who can do that work for me now."

I'm fine doing this for myself. The trouble is doing this for yourself in many environments gets you marked as insubordinate or aggressive.

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This is true. I've tried to lean more into playing dumb/innocent than being firm or aggressive about boundaries. Learning how to say "oh I'm not sure!" when someone asks me a question that's not in my scope, and resisting the impulse to follow it up with "but I can probably help you find out!!". Trying to leverage apathy/innocence instead of assertiveness and firm boundaries, because you're right, some people will interpret boundaries as rudeness.

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I'm obsessed with this comment, because I think you get to the base of something really important about modern work. You're totally taking responsibility for part of it, but there is another substantial side to this.

Yes, you may have some anxiety that unhelpfully contributes to your relationship to work, inventing problems or making existing ones more acute. But a truly healthy work culture will tell you not to worry, and help you avoid it by being super clear about what's expected and what's not, having really clear and open communication practices, and generally being really concerned with how you're doing your work and how you're developing in your skills.

Is this too much to ask for? No. Just like we should all expect and work towards relationships with partners who are open to new ideas and communicate clearly, we should expect and work towards work environments that support us and clearly communicate how valuable we are.

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You're onto something here.

As hard as restaurant work can be, it's fun to work in a decent restaurant or bar. The same can be said of working independent retail in a funky neighborhood with colorful regular customers.

These are places with flat status hierarchies. Even the owners of these places sometimes like to feel and act like one of the crew.

Corporate work takes place in a fantasy world. The CEO is director and writer. The workers are expected to be method actors. The picture never ends, so we end up like those method actors who absorb their characters' insanity.

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I'm training for a job which will not be "fun" - as a queer gender diverse midwife, it will be a whole lot of battles of varying magnitudes. But I'm in it for fulfilment, for walking alongside queer and gender diverse people in their journey. "Fun" doesn't really enter into the equation, but supportive work mates and a hope of team leads who have my back is what will make the hard work possible.

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