Consistently unsatisfied with my career - how do I find a job that I enjoy (it doesn't have to be my passion)? I feel like I'm going around in circles. Please help!

My professional life has generally been a series of jumping from one job or contract to another because I get unbearably bored of the work. When I successfully obtain a new freelance writing project or a marketing role, I experience the initial high of getting a "shiny new toy", due equally to the potential of actually enjoying the job, as well as that external validation of these companies trusting me enough to work with them.

This isn't to say I've hated every job I've had, there have definitely been some very enjoyable moments, moments where I find myself in a state of flow / in the zone, but for the most part, I feel bored and unfulfilled. This all leads to a constant feeling of existential dread. Sometimes it's buried deep under the surface, other times it weighs on me like a ton of bricks.

Since I'm soliciting advice, it would be helpful to know what I DO enjoy in terms of work.

Well, I started a blog about a year ago, the concept being to interview people who are achieving extraordinary feats in their field. I didn't have to force myself to work on it, I would stay up late working on it when I didn't have to, I would think about it in the shower, before bed, when I woke up, whenever. I could brainstorm a list of people I could interview pretty effortlessly. It wasn't easy to run a blog, but it was easy to put time and effort into it because I enjoy it so much. From high-performing athletes, experts in psychedelic medicine, authors, activists, entrepreneurs, entertainers etc. I wanted to talk to everyone, tell their story and learn from them. That to me would be close to a dream job (I don't know what my dream job would be at this point, but I think that's pretty close). I wanted to turn it into a podcast at some point.

The blog is still live but I haven't worked on it in ages because dolla dolla bills y'all. It's a passion project that I wanted to monetize but it's HARD to do that. I feel like I would need to dedicate all my time on it, but I can't because, again I need a paying job to pay bills and save for my future.

Several years ago I did something similar for a digital magazine (volunteer position, I was just starting to build my writing portfolio) and I really enjoyed the job. I had to quit because I can't volunteer forever (and my boss was a total F weirdo).

Another thing I enjoyed, and these were actually paid gigs, was writing a few stories for an online publication that explores a variety of social issues that are affecting Canadians every day. I had to interview people and research the topic. Unfortunately there haven't been any full-time opportunities there, so I had to give that up for the full-time job I have now.

The current company I work for, the mission is one that I can really get behind, I love that their focus is about making a positive impact on the world, but the work itself is boring.

The same thing happened at a tour company I worked at previously. Travel is a passion of mine, and somehow this travel-related company was the most boring job I've ever had! This was due to management, you could only do things a certain way, and the projects just weren't interesting.

So what the hell am I supposed to do?

Should I take some time off and really think about what I want in a career? Because I can easily find another job, but that doesn't attack the root cause of the insane dissatisfaction with my career, and even life, because I tie much of my identity and value to my work. If I do that, how do I "structure" that thinking? I feel like I'd need to have a plan of action instead of just aimlessly "thinking about what I want".

I do know that when I'm learning about interesting things and talking to interesting people, that's when I enjoy the work I'm doing. Also repetitive tasks are the death of me.

Any thoughts or feedback would be much appreciated.

Some things I thought might work for you (probably things you've already thought about) Travel writer, ghostwriter, work in television? Publishing? I 100% think you should take time off and think about your career - even a few days in a different setting can help you feel more connected to yourself and your mission. The blog also sounds great, and perhaps spending some time thinking about quick ways to monetize that or repurpose content on aother platform that is easier to monetize? (e.g. YouTube) even creating an e-book that showcases some of what you learnt re. interview techniques might be useful for some people or an online course that explores how you started your blog and were able to speak to so many interesting people?Personally, I was in this position not too long ago and drafted a blog on how I thought about what I wanted to do: you're after more structure, I did a template of my career including all major projects I've worked on, what I did on them, and then what career categories they could fit into. It gave me the time and space to reflect on what aspects of my work I liked, and could do regularly without fail. Good luck!
Thanks so much for your insight and the article! I'll take a look. Anyone who knows me might immediately think travel writer is the job for me, but I don't actually think I would like doing that. I wouldn't be able to enjoy my travels if I had to constantly think about writing about a place! Unless it was National Geographic-style travel writing. With regards to publishing - I've always wanted to work for a book-related company - but again, I wonder if I would fall into that same pattern of liking the subject matter so to speak (I LOVE reading), but maybe the job itself would be boring since it's likely that I would be devouring books. That review of your career thus far sounds practical and useful, I'll try that! You know, lately I discovered I really enjoy writing cheeky facebook marketplace ads - too bad I can't get paid for that lol
Hi, I've been where you are, clear in your interests and passions but lacking enthusiasm for work. I've found that the closer my day job aligns to my passion the less I like it. Why? Because work is exactly that, work. Deadlines, meetings, etc, things I don't want to do. I've found much better balance separating my passion from my income. I still enjoy work but I don't expect it to fuel me the way my passion projects do. I also don't burden my passion projects with the need to be monetized. I suggest reading Elizabeth Gilbert's Big Magic which tackles how we look at creativity. I also suggest getting a life/career coach who can help you create the structure to identify what you want. You may find out that how you like to work is very specific, that there is a certain amount of money that you need to maintain your life, that there's a limit to how much you can pursue your interests before they become laborious. Good luck.
Thank you for your response. Yeah as I mentioned I'm not too concerned with making my passion my job, I just want something I enjoy most of the time without being bored as hell. I mean, it would be ideal if my passion was my job, but I'm not going to drive myself crazy trying to achieve that. I've considered a career coach a lot lately so I might just enlist the help of one...
Hi @Treasa92! Sharing a structure - you get to gather the info and make the choices here, but providing a rubric to move through. 1 - Accept that you get to enjoy what you do for work. You deserve it. You don't have to love 100% every single minute of work, but it's fair to ask that 60% of your time, you're content in what you do. This step is does not happen instantaneously, but the intention has to come at the start or else your other steps will be fueled by intentions that won't serve you. 2 - Self-reflection. Explore what you like and don't, what has worked and what hasn't. Map out your job values and standards. 3 - Explore options. Talk to folks in roles that you think you might enjoy, listen to the pros and cons, evaluate how they stack up against the values and standards you identified. 4 - Make a choice of which path you're going to take next. Give yourself a deadline to timebox it. Roughly 4-6 weeks after you start step #2. 5 - Take action in service of the path you've chosen. Give yourself 4-6 weeks to put your chosen plan into play. I've got a longer-form post in this area over here, in case it's helpful. You've got this!
Thank you Tory! Yes I can't wait to consistently enjoy my job and not dread the work week haha. I'll check out your post :)
I want to highlight and reflect back this wisdom that you have around the excitement around something new/external validation vs. something that is long-term aligned and fulfilling. Having a good handle on how those shades of good feel differently within you, will be key. Also, good for you for recognizing that it is a pattern and that hopping to the next thing without getting to the root of it will be a temporary fix. I'm getting an entrepreneurial vibe here and I'm curious - if you knew you could make a sustainable living from it would you choose entrepreneurship over working for someone else?Sometimes we stop ourselves from wanting what we really want because we imagine that it's not possible or it will be too difficult. When we don't fully allow ourselves to be in touch with the desire, in favor of our practical mind, we can end up getting caught in a loop. This is why I like to separate the process of dreaming/visioning vs. strategic planning and implementation. They are two different parts of us and mind modes. What is your sense - if you got to choose (and you knew it would work out/putting doubts on hold) what would you be doing with your days?
Thanks for your post Sara :) Can you expand on what you mean by "Having a good handle on how those shades of good feel differently within you, will be key."? Long post incoming...I often flip flop back and forth between feeling like I'm an entrepreneur to a regular job kinda person. At this point I feel like I'm somewhere in the middle, which is why I've been freelance writing on and off for several years now. I guess a freelancer would be a "solopreneur". But I don't mind working for a company if they allow remote work, offer generous and flexible vacation time, have a great work culture and pays well.To answer your question more directly, if I knew I could sustain myself financially being an entrepreneur, I would choose to be that. However, I wouldn't want to work crazy hours every week, I don't want to live to work. And I think that's why I wouldn't become a full fledged entrepreneur. I got into freelancing partly because I wanted to work less and make more money haha, which is possible. It just takes a lot of time to get to that point."Sometimes we stop ourselves from wanting what we really want because we imagine that it's not possible or it will be too difficult. When we don't fully allow ourselves to be in touch with the desire, in favor of our practical mind, we can end up getting caught in a loop." I definitely relate to this on a professional and personal level.Professionally speaking, if I could choose, I would definitely work on my blog (and eventual podcast) that I mentioned in my post. And maybe do some journalistic writing on the side (also mentioned in my post). Full disclosure, it's totally possible that I could get bored at some point, or maybe not at all and I could love it forever. That's the thing, I just don't know since I'm confused right now about what to do with my career.I also realize I need to be creating stuff. For example, in my current job, I'm responsible for creating basic graphics in Canva. I'm not a designer by any means, I'm the best they've got and essentially I edit pre-made templates lol, but I find these tasks to be fun. Same idea with writing a blog on a topic I enjoy. And I mentioned this in a previous comment, but things like writing cheeky facebook marketplace ads is a lot of much fun for me lol. Creating marketing plans and strategy is fun to a certain extent but I think I enjoy the tactical execution more.
After reading this post and your comments, I relate to you a LOT because a) I hate routine because it's boring, and b) I need routine to feel secure.The way this shakes out in my life is that I'm a perpetual contractor. The reason this works for me is that I've gotten really good at saving. When the money is flowing, I'm squirreling it away so that when it stops flowing, I don't have to freak out and go looking for that regular job if I don't want to. I know this pattern works for me because in the past, I've gone the opposite way and taken the regular job out of a fear for my own financial security back when I had no saving habit. I lasted, in general, about two years at any given job before needing something different to stay engaged because the work was so basic (and back then, basic was all I was qualified to do even though I was intellectually capable of more). So I had to have a big sit down with myself and figure out what I wanted: variety or security. I wanted both, but I realized that my vision of security was one I inherited from the way my parents and elders had structured their work lives, and I needed to redefine "security" for myself. It doesn't mean a regular paycheck anymore; now, it means not falling below a certain point in my savings while still being able to pay all my bills and make deposits to any investment or retirement accounts I've got going. If I dip below whatever balance I've set for my savings account, I do whatever I can -- including getting side work like a retail job, admin job, or temp work -- to bring it back up to a comfortable spot. Once it's comfortable for me, I shift my focus back to full-time freelance.To counterbalance the weirdness that comes with freelancing, I follow the Gustave Flaubert model: "Be steady and well-ordered in your life so that you can be fierce and original in your work." I am extremely ordered and minimalist in almost every other area. I schedule in regular exercise, I schedule in time with my husband, I keep a very neat calendar, I keep a capsule wardrobe closet, my house is always clean [enough], I have a morning routine that I never deviate from, I keep my expenses minimal, etc. -- I incorporate this kind of routine to feel secure, and that way, it doesn't need to come from my work. It comes from lifestyle instead. I can allow work to be wild, unpredictable, fun, challenging, and spontaneous because it will not make my life chaotic since the rest of my life is pretty well battoned down.The challenge of being a freelancer is where it's at for me right now. It's scary at times, but I'm a bit of a thrill-seeker (which was a big surprise to me, lol). It sounds like you are, too. I don't know if my personal experience here helps, but I hope it might kick off an idea that's useful. Best of luck!
Thanks for sharing Jasmine :) I definitely relate to a lot of what you're saying. I'd say I'm pretty stable in my life. But I feel the pressure to make more money because a lot of my peers make more than me. Also because I don't have a nice pension I need to think about retirement. Full time jobs often come with benefits as well as a steady paycheck. Pressure from parents to have a more stable job is also very real.Finding jobs as a freelancer is a job in itself and looking for those regular clients that give you interesting work and are fun to work with his hard. I had a few regular clients but the work was either boring or they didn't need my help enough to pay the bills. I got annoyed looking for different jobs so I opted for a full time job (yet again). Maybe I should try harder as a freelancer to find those ideal clients?I like thrill seeking and letting loose too, but more through activities like skydiving and via ferrata, or going out to some underground club, not though my job haha.
I get it! You do you.The two things I'd personally advise against while figuring things out are a) comparing your income to what others are making, because who cares, you won't be proud you made more money than your friends at the end of your life; and b) pressure from parents is not fair of them, even if it feels normal because of your culture or upbringing. The goal here is to feel gratified with your own choices, yes? You can't make a decision for three people. You can make decisions for yourself, and they can learn to live with your decisions. That's how adulthood and maturity work.Good luck!