Leaving the office?
October 31, 2012 10:01 AM   Subscribe

Did you leave the office job for a year or more of trying to make it on your own? How did it go? Would you do it again? What would you go back in time and tell yourself?

I have enough savings to take at least a year off work.

I have a small income stream from established freelance work. I'm healthy. I would not have insurance if I left my job. My job will not be held for me. My only debt is one very low interest loan < $10,000, which I could maintain even if everything goes all to shit afterward and I'm unable to step back into a position similar to the one I'm leaving.

If I took a year off, I would be working more than I do now, but in a self-directed manner. I'm generally happy (not depressed, lots of great things in my life, etc.), but my workplace is mildly toxic and I think it would be a huge psychological and emotional benefit for me to kiss it goodbye.

Whenever I consider life, the reality and finality of death, and the limitations of middle-class success in America, I question the ultimate value of working for others in return for health care, retirement, a steady income, and two weeks of vacation a year. I think I owe it to myself to spend serious time in search of a better arrangement.

I believe the freelance work and side projects would be sufficient to explain any gaps in my resume if/when I resume looking for a job. I think there's a small chance (20%, maybe) that I could transition into full self employment, if one of the side projects pans out. I also think I could expand my network during this time and possibly leverage that into more varied and interesting opportunities to make ends meat.

I've generally taken very safe paths in life, and feel like this amount of self-reliance and risk is something that should be experienced, and soon. I want to fit this in before it no longer makes sense: I'm close to 30, and I have no family. There may not be a better time. I'm self directed and believe that it would be an exceptionally productive time.

What should I consider before taking any action? Do you have any horror or success stories to share?
posted by jsturgill to Work & Money (14 answers total) 15 users marked this as a favorite
The biggest dangers are procrastination and boredom. Besides getting hit by a bus that is. It's dangerous to go without health insurance even if you are healthy now.
posted by bq at 10:08 AM on October 31, 2012

My boyfriend is a little younger then you. His work place was very toxic, to the point where his boss could potentially make him seem like a very bad person. He put in his two weeks notice. He saved up a bunch of money so he could pay off college loans, eat, and buy whatever until February. He left his job in July....he had the same hopes as you did too but he hasn't done anything yet. He is depressed now. Can't find a job and February isn't too far away....

Just an example. Hope everything works out for you.
posted by Autumn89 at 10:13 AM on October 31, 2012

I left corproate America to teach kids in the ghetto.

Within the first hour I knew it was a HUGE mistake.

What I envisioned: That I would be the ONE who made the difference. I would teach English in a relevant and hip way. The kids would love being in my class because I was so interesting and exciting.

The reality: The kids were undisciplined, in every possible sense of the word. Not one kid thought that English was worth learning. The gaps between where they were and where they should be skill-wise were enormous. Scarily so.

What happened: I worked for two years. My blood-pressure shot up to 180/120. I was angry and frustrated ALL THE TIME! Finally, I sold my house in Florida and moved to Nashville, so that I could go back to working with the Phone Company.

The mere change from the Florida office to the Nashville office was tremendous. I was happy, I got promoted, I got transferred to Atlanta.

If I could go back in time I would say, "Stick it out where you are, get a job doing what you like doing. Teaching isn't what you expect it to be. The pay stinks and you'll rack up debt. Your health will suffer. DON'T DO IT!"

So my advice to you is to find a job in the same industry in a new workplace. And for heaven's sake, KEEP YOUR INSURANCE!
posted by Ruthless Bunny at 10:21 AM on October 31, 2012 [2 favorites]

Yup, I've done this. I hated working for the man with a passion and I have loved, loved, loved the self-directed nature of my work.

That being said, with it comes a lot of financial insecurity and hustling. It's a big price to pay in some ways, and there are definitely days when I envy my friends' 401ks and savings and stability.

If you switch to freelance, I'd recommend that you always shower and get dressed and try to leave the house at least once a day. Once a week, go to a coffee shop to work or something. It's good to be around people. My anxiety was skyhigh the first few months because I got so used to working in a peopleless cave that even going to the supermarket was stressful. Now that I've worked on balancing my introversion with my need to be a functioning human being, I'm much happier.
posted by PhoBWanKenobi at 10:25 AM on October 31, 2012 [3 favorites]

I transitioned from employee to full-time self employment six years ago. I did not have the intention of finding another job, and had to make it work. I continue to do that as a freelancer.

My advice would be to be a hard-ass about cashflow projections, tax savings, billables and invoice payments from the start. The big contract that pays 3 months late will literally kill you. You very likely cannot afford to have those clients.
posted by DarlingBri at 10:28 AM on October 31, 2012 [2 favorites]

I did this and never went back. I did it more gradually, though, building up freelance clients until I could cut loose without a ton of worry, though there's always risk involved. I also cut my living expenses way down to reduce pressure on myself. Some things to consider:

- Line up a good paying project or two to keep yourself focused and busy.
- Leave on the best possible terms. My last employer became a good-paying client.
- Set aside time each week to market yourself and build your business. Treat yourself like one of your own clients.
- Focus on professional, established clients with deep pockets. Avoid working with startups, other freelancers, or small businesses.
- Use COBRA or whatever health insurance-continuation service is available. If you're still freelancing when it's about to run out, try to join a group or trade association that offers group insurance. If that doesn't work, you can probably buy individual insurance for the self-employed (I did).
- Find other self-employed people to hang out with. I increasingly had less in common with people who worked jobs.
- Get out of the house every day. Work in a cafe, meet a friend for lunch...
- Consider incorporating (e.g. a one-person LLC) to get some protection.
- Consider errors & omissions insurance if your work exposes you to that sort of risk. I had to carry it a couple of times for some big clients.

I ultimately dealt with the health insurance and medical costs by leaving the US. Because my clients are happy to work online, the move didn't affect my business, and my quality of life improved immensely.
posted by ceiba at 10:32 AM on October 31, 2012 [5 favorites]

There are two things I wish I'd known before going freelance.

First is that it can be surprisingly lonely. Don't slip into a sweatpants-all-day-and-eating-over-the-sink lifestyle; get yourself out of the house sometimes.

Second is that it's important to separate work time from play time. It's very easy to start to feel "on the clock" twenty four hours a day, which can be really draining -- or alternatively for the absence of someone watching over your shoulder to let you procrastinate and websurf instead of working. At various times I've been prone to both of those faults. It helps to establish specific work hours, or even a specific work area in the house: when you're in the "office" you are at work, even if the "office" is just another room at home. When you're not in the "office", turn off your email.

Other than that it sounds like you're ready -- you have realistic expectations and an established base to work from. Go for it.

(And, yeah, keep your insurance. Even if you wind up paying full freight, it's worth it.)
posted by ook at 10:38 AM on October 31, 2012 [2 favorites]

I spent a lot of time getting laid off. Seriously, it was about once or twice a year. So the second time it happened, I decided I was going to get to the point where I never again had to experience that sick, helpless feeling of not being able to pay my bills. Also, quite frankly, having "Eff You" money is a good feeling.

So I started freelancing and by the time I got laid off for the fourth time...I came home, spun up my freelance work, and was far too busy doing work and paying bills to go to job interviews. When I started getting annoyed at job interviews because I knew I was losing a couple hundred dollars worth of work for a bunch of blah-blah-blah about where I saw myself in five years, I figured I'd just keep doing it and see how it went. That was a little over a year ago.

Caveat, though, is that my wife covers our health insurance and going without wouldn't be an option.

I would say it's going pretty well. The 40 hour a week freelance gig that covers most of my bills isn't my favorite thing in the world, but my tolerance for crap is much higher when I'm comfortably chilling at home and know I can walk away at any point. The rest of my gigs are more cyclical, so how busy I am ebbs and flows between "real busy" and "oh god".

However, here's some of the downsides.

For one thing, I've basically given up career progression in my field, because there is no higher level of responsibility to move up to. Some places would look fondly on "guy that runs his own business" but some places want to see that movement from "Assistant-Mid-level-low level management-management" and I don't have that. I wasn't particularly concerned about being on the management track anyway, but you might be.

If you're going freelance, you have to be prepared to hustle. You always have to be hustling. Because relying on one flow of cash is a bad idea when you're a regular employee, but it's the kiss of death if you're a freelancer when that big client suddenly doesn't pay up or vanishes or goes out of business or the work tails off. It turns you into a real hardass. I've said, "Eff You, pay me" more times than I care to think. I've lost friends because they thought because we were friends so they could skate on paying me.

You don't get days off anymore. I mean, you do, but if you take a week off, you know exactly how much that's going to cost you. A week off for me is about $1000, which is my rent. Do I want to take a week off and not pay my rent?

Likewise, it can take over your life. I have about 2-3 hours of free time a day because I have my paying gigs, my lower-paying gigs that may turn into something, and the work I'm doing and stuff I'm learning that may one day turn into paying gigs. Freelancing is not a lifestyle where you get to put 40 hours in, then go home, safe and secure in the knowledge that your employer (probably) won't vanish tomorrow.

Now, what do I get? I get to work on things I want to work on. Seriously, one of my clients has a web-based system where I log in, get an assignment, do the assignment, report the time spent, and get paid. I don't have to talk to anyone or deal with anything except Finance when I send in my invoice. It's the greatest gig for me. I learn a lot of new stuff just from necessity. I get a mobile lifestyle. Maybe I want to move to California or to a country with real healthcare in a few years, no disruption professionally. I don't have to deal with office politics or manage people's feelings or egos. You don't like me? End my contract, I'll get another client. You want me to sit in a bunch of meetings where I never accomplish anything? Sounds good, here's the fee that'll cost you. You want me to work rush over the weekend because you dicked around til Friday afternoon and need it NOW NOW NOW? Here's my rush rates. Other departments are playing politics? Hell if I care, I'm just a freelancer. I get to do what I always wanted out of work which is: Show up, do good work, knock off for the day, rather than deal with managing departmental politics or who likes who or any of the other BS in a corporate environment.
posted by Ghostride The Whip at 10:51 AM on October 31, 2012 [4 favorites]

I made this jump about 4 years ago and I'm glad that I did. At this point, returning to a corporate work place is my vision of hell, but this may be my own problem (I never liked following another person's schedule, priorities, just all of it).

Some things that I would tell myself if I could go back in time or that you learn along the way (giving you the same suggestions since freelance work is what you state is part of your plan):

• Be vigilant about invoicing and following up if someone does not pay during the agreed upon time (let's just say that I had a lot of stress/anxiety chasing my checks in the first 6 months, and there is even an anony ask meta about this....). But seriously, make a plan for this out in advance. If someone at the late-paying company likes your work, tell them that you are having problems with the accounts department,and sometimes they will fix this for you. Call accounts payable the day that your check is late and ask when the check will appear, what is happening, and tell them that you will be calling back one week from the date that you called to check on the status. Do this until it appears. Don't have this problem anymore because I am more vigilant about this now and ...I drop clients if they can't do this, but YMMV.

• You know how you can recognize that you have a toxic work place and now after this experience, you will not walk back into a workplace if you know that they will be like this? The same will apply to clients. So my current strategy is if a new client gives you a project, do your best - follow directions, turn it on time (or early), communicate, etc. ...it doesn't take much to become a preferred vendor. But this is what I wish I had learned early on: You should be evaluating them, too. Do they pay on time or do you need to chase checks? Are they organized? Ideally, do a test project with a new client and if they fail, drop them. Trust me, there are great clients out there, and it can be a pleasant work life.

• As a caution, I don't think that I was prepared for the fear and anxiety about money will probably seep into your life if you do this. As an employee, I usually only had a few months (if that) savings most of the time; now that I'm independent, I'm not comfortable unless I have 6 months if not more sitting in a bank. I think that fear will be there as long as I continue to work outside the normal corporate type jobs.

I don't know if I want to use the word success because this is just life, but ....I'm very glad that I did this. Some of the plusses (for me): I do get the type of projects that I want, work significantly fewer hours, feel more at balance (no coworkers, don't have to deal with people all day), more freedom in my schedule. If there things that you value (maybe you want to travel for a month, or maybe you want to attend a lecture on topic Y related to your industry), you have the freedom to do so. BUT it may cost money or a client (i.e. you can't take a project, they may not establish a relationship with you, and you may not get that chance again). But you would not have even had that opportunity if you worked for someone else. But there is more freedom IMO to determine what you want to do/what do you value/etc.
posted by Wolfster at 11:25 AM on October 31, 2012

I did this. Overall it was a positive experience, though it also made me appreciate the advantages of a regular office job in a new way.

Things I would tell my past self if I had the chance:
  • You will need to manage your cashflow more carefully than you think.
  • That hourly rate that seems so high isn't, in the end, going to give you as much money as you think.
  • You will be much more lonely working at home, alone, than you think. You will find yourself going to a cafe for coffee just for the human interaction of dealing with a barista.
  • As awesome as your home office setup is, you will find yourself spending almost half your working hours somewhere else because you want to be around people. You will develop a cafe (and public library) rotation for variety and to avoid wearing out your welcome at any one place.
  • It's OK to play video games for a week, and then crank out two weeks worth of work the following week. This is your way of working, and it is very effective for you. However, clients don't need to know the details of how you work, and it is probably best if they are insulated from them.
  • Taxes: deal with them. For real, you should pay self-employment tax as you go.
  • If you're a successful freelancer, clients will probably want to hire you as a full-timer at some point. Be prepared for that so you can make good decisions when the offers come.
  • Returning to a standard office environment (even a tech startup) may feel a little like dying. But you can also get used to it again.
  • You will have a lot of freedom; make sure to enjoy it.

posted by jjwiseman at 12:45 PM on October 31, 2012 [2 favorites]

The lack of insurance would scare me. I was healthy, too...Right up until my T11/12 disc decided to rupture and I ended-up having serious back surgery, all in the space of four short months. The hospital bills totaled north of $40,000. Glad I had insurance, obviously.

Not knowing what you do, as long as you can stay current with the industry while on your sabbatical, you should be able to re-enter the workplace without too much trouble. Some fields, though, change so quickly that, unless you're doing the work every day, one can fall behind the trends quite quickly.
posted by Thorzdad at 1:26 PM on October 31, 2012

Yup, I've been doing this for about 7 years. In some ways, it has been fabulous: I'm my own boss, I make my own hours, if it rains hard and rivers are running I can usually get out and paddle, I can sleep when I want, wear what I want, work wherever I have my laptop, all the money goes to me without an employer taking a cut, I live or die by my own hand.

There have been some real downsides for me as well, the primary one being that I have no savings and plenty of debt. I'm pretty sick of not having enough income, not having a reliable paycheck, not being able to pay my bills, being responsible for every aspect of my business including those aspects I hate and/or am bad at (I'm great at the work itself, hate/am bad at marketing and maintaining/growing the business long-term). I also feel stagnant and bored, like I exhausted the possibilities of what I do a good while ago.

I know it can be done. There have been times when my business has been chugging along well. If I was even a little better at sustaining marketing efforts, I'd be in a much better place, but I've learned - at long last - that my great marketing ideas aren't worth a lot if I can't keep them up consistently over time...and, apparently, I can't.

Sooo...the balance of pros and cons have finally swung far enough to the con that I've just returned to school for a new career; One where I will have a job, a schedule, a boss, a dress code...and (I hope) ongoing, reliable work and income; a path for career growth; continuous learning; clear, concrete tasks that play to my strengths; non-me people handling marketing, budgeting and accounting; and opportunities that branch out in a lot of different directions.

Advice I'd like to give you:
- Be crystal clear what your short-, mid-, long-term goals are. Whatever they are is valid, but they must be defined and tracked.
- Continuously, honestly, re-assess how well suited you are to freelancing. This has been very, very difficult for me. I always felt like, if I could just make some cold calls, or update my website, or send some mailings, or advertise more, or keep in touch with past clients better, etc., that I would be making enough. It seemed (and seems) so simple that it's been difficult (and frustrating and depressing and embarrassing) to accept how hard it is for me. The idea of a "real" job and all that comes with it was so horrifying to me that the situation had to become impossible before I realized that the situation was indeed impossible...for me, for now.

So, bottom line? Yeah, do it. You have a plan and open eyes. Just keep it that way. And enjoy it.

Good luck.
posted by SampleSize at 2:46 PM on October 31, 2012

I did it and I have blogged about exactly how I did it - memail me for the link if you'd like. I'm in the UK but I talk about how I worked out when to jump ship, how it has gone emotionally and financially, etc.

Good luck, whatever you decide to do!
posted by LyzzyBee at 3:27 PM on October 31, 2012

I'd tell Past Me to wake up every day with a plan for that day, and I'd write than plan down the night before...this is so I spend, for example, 9 to noon actually working on a project instead of answering emails or reading old New Yorker profiles...so much more would have gotten down this way...

I'd tell Past Me that a big source of anxiety would come from thinking, "Am I doing enough? What can I be doing to get more clients/get more work/make more money/expand my business?" By that logic, it's important to have some sort of long-term plan written down so you can measure your success. Because you don't want every day to be a Build The Business day; you need Do The Work days too.
posted by st starseed at 8:31 PM on October 31, 2012

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