12 votes

I need life/career advice

Hi friends.

I need your advice. For the past 7 years I've been self-employed as a writer. I self-publish books on Amazon and other platforms and I've had a lot of successes as well as a lot of failures. It's been amazing and weird and fun and stressful. But I'm just not where I hoped I'd be this far into my career. Being a professional artist is really hard.

I write under a pen name and the stuff I write--while I do think is good and I am proud of it--it's also slightly embarrassing. I don't share it with anybody, friends or family. Most people understand when I tell them why I can't share, but I know over the years my close friends have felt a little jilted that they don't get to know my secret.

I've dabbled with leaving professional writing behind, but after so long it feels like a daunting prospect to get back into the job market. My background is in IT consulting (6 years), sysadmin and jack-of-all-trades type stuff. So I understand managing servers, virtualization, networking, troubleshooting, and so on. I do have a minor background in programming, and last year I spent a lot of time learning Python, I learned Docker, I learned Git, I spent some time diving deeper into SQL. I'm skilled in Linux (and love it, actually). I don't have any certs. This past summer, I applied to a handful of local IT jobs (I left the big city years ago and now live in a very small market, almost 3 hours away from a larger city) and didn't hear anything back. I spoke to a recruiter who wasn't very helpful at all beyond saying he thought my resume looked good. I disagree, though... I don't think my resume is that good at all.

I just don't know what to do, though. I'm 40 years old. I've always wanted to be a writer, and I'm doing it. But I'm not writing the stuff I really want to write, and it's hard to pivot. Partly because of the sunk-cost fallacy, but also because starting a new pen name is very difficult and can take years to really gain traction. A lot of days, even though I work hard and push, I still feel like I'm failing. I'm not making the kind of money I'd like. The last two COVID years were pretty hard and I didn't work as much as I should have.

My partner works at a small company on the web development team, and I'm considering trying to get a meeting with her boss (who actually really likes me) about possibly getting some kind of junior developer position. They're currently having a tough time finding developers because their pay isn't really competitive with the current market and they don't offer work from home. They mainly do PHP for client websites, and while that's not my jam, it would at least be a foot in the door for a development role. I learned to program in high school, understand a lot of the fundamentals, and had a blast with Python last year (it came very easy to me). I taught myself HTML in the 90s, know CSS, and have some basic PHP experience from my WordPress days.

When I think about having a tech job again, I really just envision being able to work in Linux full-time, work on backend problems, and just solve higher-level issues. Not really a client-facing position. In a development role, I really don't know what I'd prefer. Just command-line, backend stuff maybe. I don't really care for frontend UX stuff. I'm most concerned with a good work-life balance, being able to leave my job at the office, and feel like I'm learning and doing and helping. I've got no FAANG aspirations or any desire to be some hot shot. I just want a chill life with chill people.

But I'm really just feeling lost. What do you think I should do?

21 comments

  1. [2]
    beanie
    Link
    An observation: you mentioned that you're hesitant to pivot in your writing career by starting a new pen name (due to sunk cost fallacy and difficulty to gain traction with new pen name), yet...

    An observation: you mentioned that you're hesitant to pivot in your writing career by starting a new pen name (due to sunk cost fallacy and difficulty to gain traction with new pen name), yet you're willing to experiment with pivoting to IT/web development/etc. with a small company (where you'd be starting from a junior level position - where you'd have to work to gain traction, grow, and work up to a higher paying position, possibly with a larger company as funds in this small development company may have you hit a ceiling fast. In that case, you may find yourself within a sunk cost fallacy soon too).

    Sounds like you want a change imo. The newness may be something that is exciting to you. You already know the writing business, starting a new pen name, as you mentioned, will probably take time to gain traction, but a caveat is that you're coming from a more experienced/knowledgeable level, so hopefully the traction wouldn't be as slow as the first time 'round. But that doesn't mean you can't do it on the side or do it later on in life... or not at all, maybe it's okay to have writing as something you did in the past. Our interests change.

    I just hope you aren't looking at this to spend more time with your partner. Or maybe only jumping into it because, well, someone likes you and we like to be liked and receive gratification/ connection. I don't get that vibe from you though.

    Just a different perspective. Can't say I'm giving advice. Just a thought.

    10 votes
    1. simplify
      Link Parent
      Thank you for your perspective. Pivoting to IT/development is really just a step back into the world I used to be in. It would also be an immediate and substantial raise in income, which would be...

      Thank you for your perspective. Pivoting to IT/development is really just a step back into the world I used to be in. It would also be an immediate and substantial raise in income, which would be nice. My two passions in life have always been technology and writing, and all the way back in college I made the choice to follow the writing path over technology. While I don't regret my choices, my life would certainly be a lot more cushy had I opted to study computer science over writing. Even so, with my skills and personality, I was able to become an IT professional and with enough perseverance I'm sure I could get back into it.

      I think I am ready for a change. Pulp writing is a treadmill and it's only become more competitive as the years have gone on. Maybe that's what's keeping me from starting up a new pen name that's more "me"--maybe I just don't have the fight in me anymore. Our interests do indeed change. I'll never stop writing. But it might be nice to spend a year or two on a novel instead of writing a book in a month.

      2 votes
  2. [4]
    HotPants
    Link
    Have you tried for a few interviews at remote first companies in order to test the water? Have you published at least one book under your real name that you would be proud of? What about a short...

    Have you tried for a few interviews at remote first companies in order to test the water?

    Have you published at least one book under your real name that you would be proud of? What about a short story?

    What does your wife think of your writing skills? I presume she is one of the few who know your pen name and has read your works?

    Whatever you decide, you should feel really proud of yourself. You are an author. You make your living from the pen. You are self published. You are a self made artist.

    6 votes
    1. [3]
      simplify
      Link Parent
      I am very proud of what I've accomplished. It's pretty crazy that I've made this work for so long. I haven't published anything under my real name, though, and I don't plan to. What I do hope to...

      I am very proud of what I've accomplished. It's pretty crazy that I've made this work for so long. I haven't published anything under my real name, though, and I don't plan to. What I do hope to do is publish under a pen name that's basically me. I'm pretty private, in general, so using a pen name is a nice buffer to keep people out of my personal life.

      No, I have not had any interviews. Last summer I applied to a handful of local jobs, heard nothing back, and became discouraged. I never applied to any company outside of my town. I did create a LinkedIn at the insistence of the recruiter I spoke with, but I found that I hated LinkedIn (like I do most social media), I wiped my account of personal information, and then I found myself locked out of it. I hope to not go back to that awful website to find work.

      1 vote
      1. HotPants
        Link Parent
        In this day and age, I think you are going to find yourself at a disadvantage if you don't have a Linkedin. It wont so much matter if you take the route of hiring with someone you know, but...

        In this day and age, I think you are going to find yourself at a disadvantage if you don't have a Linkedin.

        It wont so much matter if you take the route of hiring with someone you know, but eventually you might need to hold your nose, get a google voice number, get a google email, and sign up.

        1 vote
      2. AugustusFerdinand
        Link Parent
        You do not need a LinkedIn to get a job, even a well paying one. Recruiters are, in my experience, largely useless and little more than the HR version of a shady "SEO" contractor. Their entire...

        I did create a LinkedIn at the insistence of the recruiter I spoke with, but I found that I hated LinkedIn (like I do most social media), I wiped my account of personal information, and then I found myself locked out of it. I hope to not go back to that awful website to find work.

        You do not need a LinkedIn to get a job, even a well paying one. Recruiters are, in my experience, largely useless and little more than the HR version of a shady "SEO" contractor. Their entire strategy seems based around making you discoverable by companies looking for someone with your skillset, thing is no one does that unless they're looking for something extremely specific not the vast seas of general IT/developer/jack-of-all-trades people out there.

        Many recruiters have no other tools at their disposal other than the search bar on LinkedIn and will be out of a job if/when LinkedIn collapses.

        1 vote
  3. [2]
    wcerfgba
    Link
    I think there are two questions you are trying to answer at the same time: What do I want to do with my life? What is my passion? How can I make a living? What job should I do? The degree to which...

    I think there are two questions you are trying to answer at the same time:

    1. What do I want to do with my life? What is my passion?
    2. How can I make a living? What job should I do?

    The degree to which you want these questions to interact, and the degree to which any one answer will overlap these questions, is highly fluid. Some options:

    • Job must also be passion. Try and make a living writing exactly what I want to write.
    • Job must be enjoyable and pay well, but not necessarily be my passion. Get a DevOps job in tech which is interesting and in demand. Pursue passion writing in spare time.
    • Job satisfaction doesn't matter, I just need money. Take a random part-time job and focus on maximising free time to work on passion writing.

    I would suggest to think about your long-term objectives and work back from there, I have found that has helped me with aligning what I'm doing now, what I want to be doing in a few years, and what I want to have achieved before I leave this plane.

    Part-time might be a good option: less money, but more time to work on your passions. You could probably pursue that through a job in tech as well, either by being open about that at recruitment time, or just by finding a good place to work and then trying to swing it after a few months.

    The job with your partner's company sounds like an ideal way to get your foot in the door. You might be able to take on more sysadmin/DevOps responsibilities over time and really enjoy it. Otherwise it just gets you something on your CV to help you start moving along the dev career path.

    Good luck! x

    5 votes
    1. simplify
      Link Parent
      I have a difficult time determining my long-term objectives. I'm not really money or stuff driven. I'm childfree. I threw myself into writing full-time because being an author was all I ever...

      I have a difficult time determining my long-term objectives. I'm not really money or stuff driven. I'm childfree. I threw myself into writing full-time because being an author was all I ever really wanted. But being an author isn't what it used to be, or maybe it just never was what we think it is. I also feel pretty divorced from the culture of America now, and would never want to be famous because of it. What I've discovered that I love most about writing is that it's really rewarding to entertain people and make them happy.

      So when I ask, "what do I want to do with my life?"--well, I just don't know. I want to write, I guess. I don't care about working to some retirement and just laying around and relaxing later in life. I'd rather just write until I keel over at my desk, you know? But being an artist and an entertainer is very hard work, often for little reward. I still have to survive in this increasingly expensive world.

      2 votes
  4. [3]
    rogue_cricket
    Link
    Sounds like you'd be a good fit for a DevOps type position. Or what do they call them now - "reliability engineers"? Haha. Something like that. Breaking in would be the hardest part, though, so I...

    Sounds like you'd be a good fit for a DevOps type position. Or what do they call them now - "reliability engineers"? Haha. Something like that.

    Breaking in would be the hardest part, though, so I am also on team "really consider that small company, at least for a little while". And a lot of the important part of the experience is just working professionally in software development in general - getting used to the pace, the tools, the organization - regardless of the end product or the language. Just the confidence to get your hands on something and learn it. If you can get any kind of mentoring or do any shadowing, that's very valuable.

    In software it's also very very common to change jobs every couple years, leveraging your previous experience to get new experience in a new thing. Don't feel like one job will lock you in to one thing. I went from writing virtual machines in Assembly (don't recommend) to writing automation in JavaScript to writing phone services in Lisp and now I'm trying to get a job doing data analysis in Python. You just take bits and pieces from each previous thing and fill out what you're missing at the new place on the job, and it gets easier to do that every time.

    3 votes
    1. simplify
      Link Parent
      I've been told that before, that I would be a good fit for DevOps/reliability engineer. But as you say, breaking in is hard and where I live there just aren't a lot of opportunities. For remote...

      I've been told that before, that I would be a good fit for DevOps/reliability engineer. But as you say, breaking in is hard and where I live there just aren't a lot of opportunities. For remote jobs, I would be competing with people who have much more experience than me. I think the potential local opportunity at the place my partner works, regardless of what kind of job it is, would at least get me doing something tech-related again. I don't imagine I'd stay there more than a few years. But it's a good bet because it's easiest to get jobs when you know someone who likes you on the inside.

      Down the line, I could see us leaving this small town for something else, if that's what our careers required. But that's kind of disappointing, because we really like this place. There's just not a lot of career opportunity.

      2 votes
    2. Wulfsta
      Link Parent
      I was thinking the same thing - a test engineer position would probably be a good fit.

      I was thinking the same thing - a test engineer position would probably be a good fit.

      1 vote
  5. [2]
    Jakobeha
    Link
    I think you should work for the company and write the stuff you want in your free time. It's general advice that you can't usually "do what you love" as your job. Even if you were to get good...

    I think you should work for the company and write the stuff you want in your free time.

    It's general advice that you can't usually "do what you love" as your job. Even if you were to get good money writing what you want, if it's your only source of income, eventually you'll get bored.

    At the same time, having a job doesn't mean you have to devote all your time and energy to the job, in fact that's generally a bad sign and it's a shame that it is kind of normalized. Clock in, work, clock out so that you have money, and then write whatever you want.

    3 votes
    1. simplify
      Link Parent
      I am kind of bored, to be honest. I've written like three dozen novels and they start to feel the same after a while. Getting a job could actually be a needed respite from this insane artistic...

      I am kind of bored, to be honest. I've written like three dozen novels and they start to feel the same after a while. Getting a job could actually be a needed respite from this insane artistic productivity I've been consumed with for so many years, and maybe writing something more meaningful in my free time could energize me once more.

      1 vote
  6. [2]
    Akir
    Link
    Personally speaking I would probably keep doing the writing job if it pays the bills, but that really depends on the mental load that it gives you. But the main reason why I say this is that...

    Personally speaking I would probably keep doing the writing job if it pays the bills, but that really depends on the mental load that it gives you. But the main reason why I say this is that hiring in the tech industry sucks far more than any other industry that I'm aware of. There's some pretty extreme ageism, many jobs are filled either by networking or nepotism, and because nobody's willing to spend any money on training, you'll probably only ever get hired if you know the specific frameworks that they're using and have proof you've completed a project using it.

    But if I were to read between the lines, it seems like your biggest ask is less about what you spend your time doing, but how you spend it and with whom. In particular It sounds like you want more social interaction in your life. And if you want to go back to tech to do that, I think it's a perfectly valid reason for it. So I think while you could take the leap and change your career, perhaps before you make such a dramatic change you should consider alternative ways to enrich your social life. For instance, consider joining a writer's group, or donating your time to a social cause (local community centers are great options!). If you want to do something technical you might want to consider becoming a freelance technology consultant and canvassing your local businesses as to how you can offer them improvements.

    3 votes
    1. simplify
      Link Parent
      I am worried about ageism, but I feel like I get mixed signals about it online. I wonder if it's only at the big tech companies or the companies that fancy themselves hip and innovative that...

      I am worried about ageism, but I feel like I get mixed signals about it online. I wonder if it's only at the big tech companies or the companies that fancy themselves hip and innovative that really want young workers. I don't have any plans or desire to move to some tech hub and find a hip job. The local job that I have connections at is extremely mundane. I think they just need someone smart who can get the work done and they've had a really tough time finding that.

      Working for yourself at home alone is pretty isolating, but I've always had a good social life. And on the same token, being back in a job with a group of people does sound fun. Working with others really helps you grow, as well, and I feel I've been missing that these last few years.

      1 vote
  7. [3]
    autumn
    Link
    I say go for the small company. In my 10+ years of dev experience, they can eventually find a role that you’ll enjoy. If they can’t, you look for a new job. Unless you really want to write the...

    I say go for the small company. In my 10+ years of dev experience, they can eventually find a role that you’ll enjoy. If they can’t, you look for a new job.

    Unless you really want to write the stuff you want to write. Can you keep writing the current stuff and slowly shift to the new stuff? I’m not super knowledgeable about how that money comes in, but it could be an option.

    2 votes
    1. [2]
      simplify
      Link Parent
      I think I have a lot to offer this small company with my varied technical skills, so I'm sure they could find a role for me. I do remember some time ago when I was out with my partner and the...

      I think I have a lot to offer this small company with my varied technical skills, so I'm sure they could find a role for me. I do remember some time ago when I was out with my partner and the boss, along with some of the other people on the web dev team, and the boss was sort of feeling me out... "so do you think you're just interested in hardware/IT or would be interested in development as well?" My partner has also said the boss has asked a few times about me in a way that sounds like he's interested in me. I'm trying not to have any expectations or really get my hopes up, but I bet I could make this happen pretty quickly.

      I have tried to slowly shift into a different pen name and it is so hard for me. I know other people do it, write under multiple pen names, but it just hasn't worked for me to multitask on it. I did try to pivot to a new pen name some years back and my first novel absolutely tanked, which I did expect because I was a new name, but it felt pretty bad. It's nice to put out a book, get immediate sales and feedback, and not worry about losing income.

      2 votes
      1. autumn
        Link Parent
        Sounds like you’re leaning toward the tech role! Crossing my fingers it works out for you and you can maybe do some of the writing you’d like to in your off-work hours. :)

        Sounds like you’re leaning toward the tech role! Crossing my fingers it works out for you and you can maybe do some of the writing you’d like to in your off-work hours. :)

        1 vote
  8. [2]
    skybrian
    Link
    I wonder if technical writing would be a good way to get a job at some kind of tech company? If it’s a small company then roles won’t be as fixed and you could end up doing more once they know you.

    I wonder if technical writing would be a good way to get a job at some kind of tech company? If it’s a small company then roles won’t be as fixed and you could end up doing more once they know you.

    2 votes
    1. simplify
      Link Parent
      I actually have really considered technical writing, and it seems there can be some good money in it. But I don't have a technical writing portfolio (though I have written some thorough READMEs on...

      I actually have really considered technical writing, and it seems there can be some good money in it. But I don't have a technical writing portfolio (though I have written some thorough READMEs on my GitHub) and I just don't know how I would break into that. But yeah, technical writing is definitely something on my radar and something I know I would excel at.

      2 votes
  9. AugustusFerdinand
    Link
    I have a friend who is also a professional writer, under a pen name, that writes uhh... romance? sexually explicit romance? erotica? smut? (we just call it smut in the friend group, even though...

    I need your advice. For the past 7 years I've been self-employed as a writer. I self-publish books on Amazon and other platforms and I've had a lot of successes as well as a lot of failures. It's been amazing and weird and fun and stressful. But I'm just not where I hoped I'd be this far into my career. Being a professional artist is really hard.

    I write under a pen name and the stuff I write--while I do think is good and I am proud of it--it's also slightly embarrassing. I don't share it with anybody, friends or family. Most people understand when I tell them why I can't share, but I know over the years my close friends have felt a little jilted that they don't get to know my secret.

    I have a friend who is also a professional writer, under a pen name, that writes uhh... romance? sexually explicit romance? erotica? smut? (we just call it smut in the friend group, even though it's no where close to being a Penthouse Forum thing, as it's just easier than whatever the genre actually is called) and like you, it took/takes a lot of work and a lot of time to get to his current point where he's self sustaining/no longer struggling to make ends meet.

    He started out under his own name, but wasn't getting anywhere quickly enough, so he worked ghostwriter for some other "big names" for awhile, getting some experience in and then went back to his own name and success has come relatively quickly since then. If you want to remain a writer, this may be an approach you can take as well. Otherwise I'll echo what @wcerfgba stated, of finding approach works best for you. The vast majority of people don't have the opportunity to do what they enjoy for a living, so you're in an advantageous situation to have done so/be doing such now.

    1 vote