Fulfilling Career
October 18, 2011 6:29 PM   Subscribe

Have you escaped office drudgery and/or being controlled in a job to launch your own independent, creative, fulfilling career? Please tell me about it.

My current job is in line with my interests and skills, and all things considered it's the best job I've ever had (at least, it was last year), but I don't want to do it anymore. I am sure about this.

The problem is, this has happened with almost every job I've had. I have had several jobs that I have absolutely loved from the beginning (or at least liked a lot) and have seemingly been well-liked by bosses and coworkers. Then, things change...I start to feel resentful that I am being asked to do pointless tasks, that I have to sit in a chair and stare at a computer screen, or that I have to follow or enforce rules that I don't agree with. That I have no autonomy (the reasons have varied). I wind up finding the job unsuitable for me and leaving after a year or two.

I suspect some mefites will say that I need to learn to play the game in order to be employed; just suck it up and follow along and collect a paycheck. But I can't. Maybe it's a flaw in my personality but I have a strong desire to set my own rules, my own schedule, and answer to myself. It's not that I'm not willing to put in the work; I just want to do it on my terms, and I want to do things that agree with in principle and that I endorse.

I don't mean to belittle anyone who works in an office or has a boss, etc. I just am pretty sure I can't do it and be happy. What I am interested in is freelance translating and writing, and through research I believe that this is something I can make a living in (esp. the translation). Basically I want to create something sustainable and satisfying, that I myself have some autonomy over, rather than jumping from organization to organization every 2 years.

So, my question is for those of you who have felt the same way and have managed to launch a satisfying career for yourself. What gave you the final push to change? How has it been? what have been the key elements in your current job satisfaction? Is there anything I am not thinking of?

Alternately, maybe some of you have personalities like mine and have managed to be happy in a more traditional career/job. In that case, what are the elements of your current career that make you like it?

I am looking for motivation, advice, experience, and maybe warnings.

posted by bearette to Work & Money (12 answers total) 34 users marked this as a favorite
I'm a freelance translator, and while the job certainly offers more autonomy than being a worker bee for a corporation, there is still a certain amount of following other people's rules, conforming to other people's schedules, doing tedious (though perhaps not entirely pointless) tasks, and of course it's almost all done sitting in a chair staring at a computer screen. Until you get established, you have to spend a lot of time selling yourself. After you get established, you are constantly having to juggle the competing needs of your many clients and your non-work life.

Instead of having one boss, you have many bosses--they are called clients. If you don't do things how they like them (submit their invoices according to their schedule, according to their nit-picky format, use their preferred CAT software, use their project management website, use their preferred terminology, fill out whatever QA forms they require), they will not be your clients for long. As far as the actual work itself, you have to enjoy the translation process, because it's often long stretches of translating birth certificates and corporate contracts in between the occasional interesting text.

I love my job, and I enjoy being a freelancer, but there are times I don't enjoy the administrative end of it. One of my biggest sources of satisfaction in the job is getting better at it--for example, becoming the "go-to" person for some agency--the one they come to saying "this is our most demanding end client, and we really want you for the project". You are, of course, free to say "yes, I can fit that in for you" or "no, I'm already booked up for the week", but it's always in the back of your mind how much freedom you really have to turn people away before they decide to find someone else. So you wind up squeezing in the extra work, setting other projects aside for the rush jobs, saying "yes" when you'd really rather say "no", agreeing to a discount off your standard rates--just to make sure you don't lose that customer.
posted by drlith at 7:16 PM on October 18, 2011 [4 favorites]

What I am interested in is freelance translating and writing, and through research I believe that this is something I can make a living in (esp. the translation).

So... do that.

Seriously, that's all there is to it. You already know what you want to do, which is like 90% of the battle. The usual way the transition plays out is:

1. Figure out what you want to do instead of Job-Job (yay, you already know!)

2. Start doing Thing You Want to Do on the side, working towards perhaps going part time at Job-Job while building Thing You Want to Do

3. Eventually, leave Job-Job and do TYWtD full time.

Is it less financially secure to do TYWtD than stay at JJ? Possibly. So what? If you are losing your mind, wtf are you staying at JJ for, really? Downsize, save money, etc., and just do your dream. Make a plan and take the leap.
posted by pupstocks at 7:16 PM on October 18, 2011 [2 favorites]

Response by poster: thanks for the helpful answers. one small thing, re: sitting and staring at a computer screen: I mean that I don't like being required to do this all day when there isn't necessarily work to be done, but if I am doing work on the computer, and can decide where to sit and when to take breaks/move, it is ok.

I'll stop thread-sitting :)
posted by bearette at 7:23 PM on October 18, 2011

I've been a freelancer in film and TV for over 20 years. My jobs might sometimes be in offices, but I've not been a staff employee anywhere since 1988. The whole field is made up of freelancers or independent contractors.
I'm always looking for a job, even in the middle of doing one. I have had semi-long stretches of unemployment, esp. when various unions have been on strike, but that's why unemployment insurance and savings were invented.
I never turn down work. If I'm not a natural extrovert, I impersonate one very well, because I never know who might be my next boss, colleague or tip for a job.
As I'm self-employed, I pay my taxes quarterly and I pay lots. I used to try to have at least 1 job a year that put me on payroll, but then I formed a company and now am on a "loan-out basis".
I can sometimes set my own schedule but if I have 1 client in London and another in Manila--my day is really, really, really long.
posted by Ideefixe at 7:24 PM on October 18, 2011

I've done a lot of freelancing as I bounced around full-time gigs the past few years, so while I haven't completely given up on ever working in an office again, I work from home on contract for a couple of regular clients at the moment. Lemme tell you, I think you're rose-colored glassesing quite a bit, because there is a LOT of drudgery and doing things you don't want to do.

For example, businesses sometimes have entire groups of people devoted to bringing in customers. If you go it alone, that's you now. You have to drum up clients all by your lonesome, then you have to deal with clients, and clients have demands that you'll go along with or you won't make money. Don't want to go to whatever mixer/function/convention is where you'll network with clients? Too damn bad, those bills aren't going to pay themselves. Businesses usually have entire accounting departments for handling boring tax issues and bill payments, and if you don't hire an accountant (I'd suggest you do once you get a respectable enough income), that's you now, too, and it's not exactly exciting stuff figuring out which tax laws apply to you (and frankly I'm glad my state doesn't have an income tax because that'd be a whole new thing to worry about). Customer service? You do that now, or you write it into your contract that they only get X revisions or Y calls, then they can pay you more, but you still probably do it.

The upside to the freelance/self-employed lifestyle is that if it's a gorgeous day out and you just can't sit in front of a computer screen, you can blow it off and go run in the park. The downside is, you don't have sick leave or paid leave, so you're costing yourself money rather than doing the Ferris Bueller routine and getting paid for it.

What I'd suggest is keep working at those soul-draining jobs to pay your bills and start building up your client list and income streams, so you don't say goodbye to all that only to discover you hate the freelance lifestyle. Maybe you really like pitching. Maybe it turns out you hate pitching people on your services and getting turned down again and again, especially in something as soul-crushing as writing. Maybe you don't mind it taking 3-6 months to get paid for something you did. (Some places are really on the ball and some places are sloooooooooooooooow, especially on the writing side and that's assuming you get paid at all).

What I did was about 2 years ago, after one of many layoffs, I decided I wasn't going to ever be stuck depending on a single source of cashflow ever again. (Don't ever depend on a single client or source of cash). I started hitting the bricks and working freelance just to pay the bills while I looked for something full-time. Once I got something full-time, I kept the freelance work up (which usually meant I'd work for 8-10 hours, then come home and work for 3-4 more) for about a year and a half, then scored a full-time job in a city that was cheap enough for me to freelance in and survive. After moving there, I worked at that job long enough to pay down moving bills and save up money. When the axe inevitably came down, I had enough clients that I had enough freelance work to pay my bills before I even made it home from the office. (It helps that my wife works, which provides our health, dental, and vision insurance and enough cash to make rent if the bottom falls out of my gigs).
posted by Ghostride The Whip at 7:27 PM on October 18, 2011 [2 favorites]

For me...what has happened a few times....a lot of the drudgery i was excited to leave behind, I actually just brought with me.
posted by ian1977 at 7:36 PM on October 18, 2011

Response by poster: I'm sorry if this is off-putting but I just want to reiterate my main question in case in got lost in my rambling up there:

"So, my question is for those of you who have felt the same way and have managed to launch a satisfying career for yourself.

Alternately, maybe some of you have personalities like mine and have managed to be happy in a more traditional career/job. In that case, what are the elements of your current career that make you like it?"

So, these answers have been useful (really) but I am not necessarily just asking about freelancing and I am especially interested in hearing from people who have similar issues as me but are happy in their job, no matter what the job is .
posted by bearette at 7:45 PM on October 18, 2011

I'm 50. I figured out in my early 20s that I was basically unemployable, because my standards were always higher than my employer's standards, and because I had little tolerance for waste and office politics. I had a "bad attitude."

As I got older I learned to hide the attitude but I still disliked jobs, so I learned to cobble together part-time jobs, which helped keep me from being so affected by the absurdities of any one workplace. But part-time contract work doesn't pay, so I began to cultivate my own clients and finally went 100% solo 5 years ago.

Once I went independent full time, I immediately got more respect and nearly doubled my hourly rate. I'm now asked by well-known companies to teach their people to do what I do, while my last employer wanted to keep me in a lowly cleanup role and refused to recognize my awesomeness.

I've developed an information product in addition to doing client work, so I have a healthy passive income that makes it possible for me to turn away problematic clients. Thanks to the flexibility of being self-employed, I've also been able to travel and now live abroad.

So I can't give you a happy story about staying in the job world. I'm way better off self-employed -- emotionally, creatively, and financially. I wish I had quit earlier. The main headaches are what others have mentioned -- admin stuff like invoicing and pestering late payers, work that I've partly eliminated by creating service packages that require payment up front with a credit card.
posted by ceiba at 7:59 PM on October 18, 2011 [2 favorites]

Yes. Having to do pointless tasks, not being able to be efficient, having to sit at a computer while not productive is absolute, total torture for me. I can't work for someone, doing something a certain way, when I know I am able to do it better my own way, but not being allowed to. I would rather work productively and quickly and then when I am done, really, truly be done, not having to pretend I am busy.

It never mattered how much I liked my bosses or co workers, having to do things that didn't make sense to me drove me so crazy that I would start to painfully dislike my job.

Having my own business has been such a blessing in so many ways, but one of the most important reasons I am so much happier is that I get to make my own decisions, and can make my own company policies.

So, it seems like I have a personality like yours, and no, I never found happiness in a 'job'.

I also call myself unemployable for the same reasons as ceiba.

note: I have never worked in an actual 'office'.
posted by Vaike at 8:06 PM on October 18, 2011 [2 favorites]

Best answer: Apologize in advance because this is a bit long, and I don't have time to edit and it may ramble a bit...

Wow, I had the exact same thought over and over and over again several years ago. I finally did find a job field/industry that I enjoyed but also found myself job hopping between every 10 months to a year....loved the coworkers, but could not take everything that you mention (pointless tasks when the workload was low, someone else controlling my schedule, etc.).

I finally did what you are thinking about doing now. I quit my job (no transition part-time work, etc., I just gave a month notice) ~3 years ago. I've been working on my own as a consultant/freelance writer since that time and I really enjoy it.In fact, this is the longest time period that I have kept a job. What I really enjoy about what I do now includes: I decide whether to do or not do the projects; I decide what I want to learn; I definitely have 10X less of "doing the pointless tasks;" I'm definitely challenged, I have control over my schedule (within limits). Also, a big plus for me was that at the "salaried, office job" ...I sometimes had to work evenings, weekends, with no monetary compensation IMO. Now, however, I'm often paid hourly for projects, so if it is a weekend/evening, it does not bother me the way it did before. I 'm also on the extreme end of introversion and enjoy not needing to deal with people every single day, but that's me. These are the things that make me happier than before and may apply to you, although there are negatives, too, which never existed in an office job. Will get to that later.

I'm just going to mention the steps and things that worked for me/advice, along with some warnings at the end. I don't know if it really will help to hear this, because in the end you have to jump and just give it a go.

What I think really worked for me was first getting a fulltime job doing what I wanted to do in the future (so perhaps get a job for a company as a translator?). In retrospect, it was one of the reasons that I get a lot of work today because...I have industry standard samples, and companies that work with me for projects know that I have the experience. Also, what really helped was making contacts at those fulltime jobs (it sounds like you will do well, too, OP, since you mention liking your coworkers). But I do know that my boss/peers respected what I did and I still get calls from some of them even now for potential projects. I also made a point at that last fulltime job to learn things on the job that I knew I would need to do as a freelancer.

Also, start saving a $ cushion now (I had at least a few months savings when I left)...my early clients did not always pay on time.

As you get closer to wanting to leave, reach out to former coworkers, potential customers, etc. (I now have a few sentence "letter of introduction" (i.e. here is what I do, some of the things that I can do for you, link to webpage, c ontact info, etc.) I had at least one person who promised me a lot of work the moment I planned to leave.

Finally, hold on to your vision and your annoyance with the workplace, and when it builds up (along with a potential customer or two, plus a few months savings), just jump. I did have a former work colleague make a very good point to me: If I continued to work and receive a monthly paycheck, what motivation would I have to look for more work or even do work? He actually told me "chain the wolf to the door." So I quit and planned to go back to a workplace if it didn't work out, but I was going to give it 6 month effort. YMMV but the only way that I could do it was to walk out the door/no small transition or parttime job.

Another thing that works for me now (although this may be dumb luck) -I don't do much marketing. I was surprised that LinkedIn works really well...companies in the US and even other countries may look for your skill set if it is unique (I actually think that you could potentially have a very good niche, by the way). Also, I do send emails to companies every few months. I could probably do more marketing, but I'm okay with the amt of work that I have now.

One more thing that really surprised me: I decided to specialize in a certain niche within a niche when I started (because I enjoyed it/it was challenging) and it has turned into more and more work.

Here are the warnings:

Finances: Just be careful (I think that I will need several months of savings forever). This is year 3 for me and I will earn more than I earned at a fulltime job this years. In years 1 and 2 I did not (and I have no idea what next year will bring).

Plan that things will become more complicated: I have to pay someone to do my taxes, I actually use a payroll service for myself, and... I did not do this/need to do this, but it is important to learn details about law (how to read contracts)- I have been burned once or twice. Unfortunately, the actual work that I do interests me a lot and everything else...not really. Oh yeah, things that were simple at a workplace (like getting a paycheck),may not be simple if you have to hound and remind a client to pay.

The greatest challenge to me has been myself (fear, constant fear). Thoughts like -- during a slow month -- are my clients leaving me? (They are not, but every year, during the slow season I think this). Also, I've really wanted to hire people part-time, especially during the crazy times of year, but I stop because I'm afraid of the things that can go wrong. Unlike a workplace, there is no one to hold your hand. There really are not people IMO to ask these questions, either (I've tried SCORE, etc., but they really were not helpful): So who do you ask if you are making your own trail? In my dream world I would find a "mentor", but I don't think that it applies anymore. Nonetheless, it is all an experiment, and I do think that I will do the things that I am afraid of some day, too. Far more likely that I will do it in this setting than working for someone else.

This is far too long. Feel free to memail me if you want, because I don't think I can hit everything.

One last thing as I preview.It depends on you, but ....there will probably be moments when you don't have much to do working for yourself, too. At a workplace, they give you silly tasks and a paycheck. If you work for yourself, well, I take a break and go on walks, travel, bike, take breaks...but I may not have any $ coming in during those times, either. I'm okay with it because at other times of the yr I make more, but I know that some freelancers/small business owners have a hard time with this. Just a warning, I don't think you will know how to view it until you are there.
posted by Wolfster at 8:57 PM on October 18, 2011 [6 favorites]

Best answer: I think I'm a lot like you. I didn't actually work in an office environment too long (less than 5 years) before getting out, but I knew from the beginning that being a cog in a machine wasn't ever going to satisfy me, even if the pay/benefits/other perks were great.

I am now a freelance food writer/food photographer who does recipe development from home and just signed a book contract. (yay!) So it's not exactly the field you're talking about, but I AM self-employed and a freelancer and very, very happy in general.

My path was this: I was spending all my non-working time at work reading food blogs, drooling over recipes, printing out ones I wanted to try, and obsessing over food in general. I'd already pursued several other "fun" careers that didn't pan out, so I wasn't sure I wanted to jump ship right away. Instead, I enrolled in a night program at a local culinary school and for the next 6 months took classes while still working my day job. Long story short, after graduation I realized I loved cooking much (much!) more than I loved the security of my office job, and I made the leap and took a $9/hour job at a local bakery.


But over the next few years, I gained experience, hopped around, earned more money, and started really discovering what I liked in the culinary world: WRITING about food, not just making it. I took a side job writing recipes at home for a website, and over the years that job grew until I could support myself doing it full-time. Restaurant work is backbreaking and for me, there was much less future in it than there is in being my own boss and developing new talents, like photography, that further my career.

I love what I do but there are downsides, too. I sometimes miss coworkers and feel isolated being home much of the day by myself. When I'm less engaged in a particular project it can be like pulling teeth to make myself finish, because I don't have the peer pressure of an office environment to motivate me to work. And the taxes! I pay a small fortune in taxes, in addition to paying an accountant to sort it out, and a lawyer to look over things like contracts.

I would say this kind of life isn't for everyone, especially those who value a steady paycheck, who like the social aspects of the workplace, and who like the reliability of knowing there will be work tomorrow, next week, and next month. But if you are like me--and it seems like you are--there is nothing more rewarding than being your own boss, and realizing that you are up until 2am working because you LOVE it, and you WANT to, not because you have to. (Or maybe you also have to...but you know what I mean.)
posted by Bella Sebastian at 9:28 PM on October 18, 2011 [1 favorite]

This sounds cliche, however it still holds true for many. The only thing limiting your life, your career is your own personal perspectives which are typically hideously skewed because of what society has told us is normal, right, responsible etc...

So that being said I recommend you first shift your attitude and really think about what you want to do and what skills or talents you may have to make it happen. Begin talking to family, friends, coworkers build up a nice community network. Then use those resources to develop your ideas/ business of whatever you decide.

Life is short, you are too intelligent more than likely to tolerate the type of job you have, I'm impressed as hell that you are willing to change...fear can be so limiting and you seem to be setting that aside where it truly belongs!

Great Luck to you!
posted by gypseefire at 5:28 PM on October 20, 2011 [2 favorites]

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