Is it time to un-hang my shingle?
June 16, 2012 7:17 AM   Subscribe

I'd like you to tell me if I should quit my job (I'm a member of the "ugh, I.T." chorus), but the snowflakey part is that it's not just my job. It's my small business. And to some degree, it's all I've got right now.

A little over five years ago, I graduated from college and, while waiting to start law school in the fall (jeez, another dumb idea, but whatever), decided to make some money as a Mac sherpa. I posted an ad on craigslist and waited.

What I did not necessarily expect was that five years later, at the age of 27, I.T. work would be my full-time occupation. That it would suck up 150% of my time and energy. That I would spend so much of my remaining moments in a depressed fugue trying to muster up the energy to even think about what else I might want to do instead. Oops.

So here's my problem: I don't feel that this is the work I'm meant to be doing, but I have been somewhat successful and have built up something with a lot of goodwill and a reasonable amount of momentum. This coming Monday is the 5th anniversary of my first paying gig, and I keep dreaming of sending all my clients an e-mail thanking them for their patronage and gently explaining that I'll be closing up shop and moving on. I've been thinking about this looming imaginary deadline for weeks.

But, of course, if I actually take this drastic step, I'll be squandering a huge resource that I've spent years building: Almost all of my clients are ongoing accounts with whom I've worked for years. Things are decently successful. My business is growing, exclusively via word of mouth, at about 50% year-over-year. We're not talking huge numbers here, but I'll do alright for myself this year, especially in contrast to many of my peers, who've spent their post-college years in this never-ending recessionary morass.

So. Should I feel more grateful for what I have, during these tough times? (It's not all bad: I've found a great niche, offering Mac support to art galleries and other creative professionals. I actually adore many of my clients.) Should I be thinking of a more intelligent way to sever the line? (For what it's worth, it would be pretty easy. My work is ad-hoc, on-location and billed hourly. I have no employees. I am not renting office space.) Is it a supremely dumb time to wander jobless through the universe? Is the grass going to actually be greener out there, or will I miss setting my own hours and schedule (which honestly drives me crazy now)? If I do shuffle off, is there a way to leverage my long roster of very satisfied clients, instead of just allowing that resource to evaporate?

(Also, don't forget to tune in next week for the next chunk of this question, in which our tortured hero describes living in the same Brooklyn neighborhood he grew up in and trying to gauge the pros and cons of leaving NYC.)
posted by anonymous to Society & Culture (23 answers total) 4 users marked this as a favorite
Is it possible you can find/train some employees/partners to do the grunt work for you? A stable list of clients is a great asset. It seems like you are doing all the work yourself, and for many businesses, at some point you need to delegate some of that labor. Hiring someone else would decrease your profit margin drastically, probably below the point at which you could live entirely off the business as you seem to have been doing, but it would free up your time and effort to pursue other things on a part-time basis without severing ties completely.
posted by permiechickie at 7:31 AM on June 16, 2012 [8 favorites]

Never quit your job until you find a new one.
posted by Brocktoon at 7:33 AM on June 16, 2012 [6 favorites]

There is a point of view that says you're making a good living, being your own boss, setting your own hours, and making bank that supports you while you live in Brooklyn and you would be very well advised not to undervalue that. (FWIW, I'm self employed and I'm not over valuing your gig, either - I know which parts suck.)

Regardless, you don't seem to have a plan for what you do after you close your business. Do you want to maybe address that here so people can give you better advice?
posted by DarlingBri at 7:35 AM on June 16, 2012 [1 favorite]

Sounds like it's time to find someone trusted who you can hire (or partner with) so that you can step back and have time to think while still making enough money to support yourself. If it's currently sucking up 150% of your time and energy then you need to offload a percentage of that suckage; and then use that freed up time and energy to think about what to do next.
posted by dgeiser13 at 7:43 AM on June 16, 2012 [1 favorite]

Can you cut back a little? Give yourself some breathing room but still make enough money to survive? While it would be fun to just go "this far and no further" it doesn't sound like you have any specific plans for after you make your wonderfully symbolic gesture (and I am all for symbolic gestures they are the best kid).

If you have no plans other than I don't want to be doing this, if you cut by your hours in an organic way by bringing in a price increase, by charging more you will drop a few clients by the wayside, but your income might not take such a hit, then you can find a better work balance and maybe even make similar money. Also making more money for the same work can help that work suddenly not seem so bad. If nothing else it would give you time to think about what you do want to do while not being completely swamped and able to think of nothing else but work you don't like. Then when you have figured out what you want and where you want to be you can set all those bridges alight and move on, it's just best not to set bridges on fire while standing on them.

Also don't be too quick to write off what you are doing if you are thinking of moving it is a handy and easily transportable skill that could help you get set up in a new location while you start to do what it is you really want to do.
posted by wwax at 7:43 AM on June 16, 2012 [3 favorites]

Start thinking about selling this major asset (your business) instead of throwing it away. In the meantime, look for a reliable sub and take a vacation!
posted by the young rope-rider at 7:55 AM on June 16, 2012 [7 favorites]

I'm very ambivalent at attempting to try to respond to your question because there are really many unknowns here. Some questions that might help us give you a better answer:
• Do you have savings to last you through finding your next job or career?
• What are you really after? More time? (You imply that with the suck up 150% of your time comment).Lack of truly having your own schedule? A job?
• When you say this is not what you are meant to do - do you have any idea of what you want to do/other interests/another degree/etc?
• Do you have visions of something else that you want to do for a while (i.e. travel the world?)

I'll throw out some other suggestions, but I think it may help people reading your question additional insight into your question.

If you are after time and/or time to explore another career, then there are ways to cut down on what you do now:
• Raise your prices, by a lot and include charging them for time to travel to work onsite. Last year I did more than okay and worked ~20 hours/week, although there were still crazy weeks/hours.
• Alternatively, set conditions that you will or will not do (can some of these projects be done from home? Then you could minimize it to work from home and not take off-site work).Or maybe it is no weekend work/whatever.
• Are there certain type of clients and/or projects that you like and prefer? Just take those and don't accept the rest (tell your clients and potential clients that you love projects x,y,z...but not 1,2,3...many respect and remember this/you can still get offers for the other stuff/but it would be tailored to what you want.

I suspect that there may be some reason that you are not hiring people. As an alternative, if there are people in your industry that you respect, you could recommend another person to fulfill that role for a client whose project that you can't take.Then there is good will all around and perhaps the person that you recommended will help you out if you need to take another client.

Anywho, I would try that to at least provide you with additional time to explore other jobs, etc. You could simultaneously take a part time job/internship and explore is this what you want to do and also keep the other clients. You may find that you don't like having little input in how the work is conducted or working someone else's weekly schedule, but YMMV and you may love it. You could also use that free time to explore ANYTHING: What about volunteering? Helping other small business owners? You could use the skills that you have already developed to transition into another job or career.

Another option if you want to try a job for a while (and you know the workload of your clients): Mention this to a few of your favorite clients. I've had some clients suggest "come work for us!" ....I wouldn't mention it unless you are serious about it.

If you just want to explore a new career path, do carve out some time, have info interviews, take a few class(es).

You know one more idea that just occurred to me since your clients like you and need the services (and need the know how)- what if you wrote up a little "how to manual" and put it up somewhere as a cheap e-book? It is your choice to give it or sell it to your clients - have your clients provide feedback, but -it may generate some income/additional awareness that you are there if you want to continue the business .
posted by Wolfster at 8:00 AM on June 16, 2012 [4 favorites]

I would recommend selling the business instead of closing it, or (if no buyers are interested yet) simply hire some people to do the grunt work for you and manage them. This will also give you valuable management and training experience on your resume, which will be infinitely useful for your next job.
posted by wolfdreams01 at 8:12 AM on June 16, 2012 [6 favorites]

What bothers me is the artificial timing (how much impact the fact that your five-year anniversary is coming up should have on this decision: absolutely none) and the fact that you seem to only be contemplating shutting down your business altogether.

It is absolutely fine to close up something you've built because it isn't going anywhere that is going to make you happy. Lost opportunities are not a real issue if you don't want the opportunities on offer.

But if you don't have a definite plan for what you're going to do instead then you're just bailing out and if you think the sudden shock and freedom will somehow kick you into figuring it all out, well all I can say is I've never known anybody that technique really worked out for, myself included. You trade one pressure for another (the inevitable expenditure of savings looming in the future and the now ramped-up anxiety of "I MUST find my Very Special Destiny now OR ELSE!) and it is easy to fall into just as bad of a "depressed fugue" without even gainful employment to provide some modicum of daily direction.

So, what's your plan? The one you've described - email all your clients on an arbitrary date - just isn't much of a plan at all. But it would be as big of a mistake to say oh well, deadline came and went, I'll just accept my unhappiness with my status quo and do nothing about it.

If you know what you're after - if you've thought it out and accumulated resources to give it an honest shot, you know, it's reasonable. Sometimes having another job in place isn't an option and you have to take chances.

There are lots of ways you can approach this transition. You could start very slow and small, by taking a hard look at the clients that cost the most time and/or stress for the money and dropping them first, looking for a better balance between workload, stress and income. Even if you're going to dive into something else, it might make a lot of sense to keep a few of your most sustainable clients. If you are ignoring obvious necessities in dealing with your depression and lack of energy (working on your diet, sleep and regimen for example) that is an issue as well. Taking that kind of thing into hand doesn't get any easier when you're unemployed. Never did for me anyway.

Make a change but make it a deliberate change, not an impulsive one. I understand the desire of the impulse, I really do - it looks like a simple, cut the knot solution to a complicated situation. But real life is seldom particularly narrative in its logic and the situation will be no less complicated when you've traded one set of complications (overwork and dissatisfaction) for another (dwindling funds and uncertainty).
posted by nanojath at 8:22 AM on June 16, 2012 [2 favorites]

idea: if you want "out", you can get a partner on board and split the business/sell your business. Or what wolfdream01 said.
posted by ruelle at 8:27 AM on June 16, 2012

As a former part owner of a small business I would say, look around for escape hatches and be prepared to change things. Definitely agree with selling rather than just walking away. Short of doing either, look at where you might be in another 5 years, then 10. It sounds like you are doing this already. Would you be ready to hire employees or a partner, or diversify-- not just to make your life better, but to keep the business going?

Our business, while not in IT, was sort of like yours in that it grew organically from something my partner decided to do for a bit on the side. There turned out to be a really good market for what he was doing. But after a few years, there were subtle outside things that changed to make the business more onerous to run, and the good parts not so good. Your business doesn't sound like it had the problems ours did, but still: If a couple of things changed (like operating costs, the availability or your time, any services you use) could it become a total pain the the ass, or impossible to run? Considering changes you might want to, or have to, make might be helpful in making this decision. This is just a gut feeling I have, that things don't stay the same when you own a business.
posted by BibiRose at 8:30 AM on June 16, 2012

Sound to me like your issue is not so much with the job, but it is the feeling of being trapped with no easy way out. I am not sure what it is, but you need to find POTENTIAL alternatives so that you can be comfortable pulling out whenever. A you get older, the thought of doing the same old job for the rest of your life get pretty darn scary. You have a lot going for you other than the business itself. The skill set and mindset necessary to be an entrepreneur from the age of 22 -27 is tremendous. Take your time and figure out what you WANT then go get it.
posted by AugustWest at 8:48 AM on June 16, 2012

Before you do anything, you need to answer a VERY IMPORTANT QUESTION: what exactly DO you want to do? Is it possible to shift your existing business so you spend more of your time doing things that make you happy, and bring in people to help you do the rest?

You've got an existing business and a solid client list. Whatever your vision of what you want to do, those can be invaluable for the next phase of your career.
posted by mikewas at 8:51 AM on June 16, 2012

Sounds to me like you don't value what you have. In other words, you have an ongoing dialogue that the grass is greener somewhere else if only you knew what it is. I did what you are doing, Mac Sherpa to creative clients in the Bay Area. When i moved to an area with less of a creative arts nexus, that business dried up and disappeared. Do I wish I had that business back. Yes. Do I wish I lived in a giant cityscape with clogged freeways and constant driving. No. I would say what you have is a prime gig that you are totally undervaluing. You are your own boss, set your own hours, get excellent least I hope so for consulting with high end businesses in NYC. You won't find that as an employee. Much better to start another business as a sideline, do some experimenting, take a few affordable risks, and see if your new business can take the place of your current one. Don't leap and hope. It's not much fun.
posted by diode at 9:18 AM on June 16, 2012

Leaving aside all of the excellent life-planning responses, there's a grey in the middle of your stay-or-go black and white thinking that's far less complex than hiring employees (which is fraught with all sorts of legal and financial issues, re: taxes, payroll, unemployment deductions, etc.) and partnering (again, long-term legal and tax headaches for what might be a short-term situation).

Instead of hiring employees, you can do either or both of the following:

--refer new client prospects to other IT providers and take a referral fee (i.e., a set dollar amount for a one-time job, or maybe 15% of the revenue for the first six months of a job)

--use 1099 independent contract workers rather than employees. You won't have to apply for an EIN, you won't have to pay FUTA or withhold taxes, and you'll be able to retain some of the revenue for yourself, under the name/construct of your own business, in case this is a temporary case of burnout.

By choosing either or both of these options, you'll keep your business in operation, earning some money, while you determine what else you might want to do. Perhaps you'll decide to close, sell, partner or hire employees. Or, maybe you'll keep owning your business while letting contractors complete all but the work you actually enjoy, keeping your clients enjoying continuity of service. You can also delegate other aspects of running the business you don't enjoy by using VAs (virtual assistants) for bookkeeping, appointment-setting, invoicing, paying the contractors, or whatever, for fairly reasonable prices. With the free time, you can figure out what you want to do with your life without ending up making a panicked, financially-induced decision when you find the assets have run out.

Finally, I once made a decision based on an arbitrary, self-imposed deadline. It's my biggest regret. You have MULTIPLE alternatives -- give yourself time to pick the best, and not just the fastest. Good luck!
posted by The Wrong Kind of Cheese at 10:57 AM on June 16, 2012

Also, in terms of jobs you're probably qualified for some CTO level positions or high-level consulting, both of which have a good salary but not a 9-5 job. You're in a good position, career-wise, to really spin your experience and skills and make bank. That said, getting high- level jobs takes time (months) so if the job market is really where you want to be, you need to budget time and have a plan that will take more like a year than a month.

Anyway, don't underestimate how difficult what you've done is--it is nothing to be ashamed of in any way. I get that feeling from that question, but you should be very proud of what you've done and built.
posted by the young rope-rider at 11:01 AM on June 16, 2012

Being self-employed is much harder than people think.

You could choose to expand the business:
Hire staff, which launches lots of paperwork, risk, general PITA.
Get an office, maybe a storefront.
and so on.

You could choose to continue, and work on identifying the bits you really dislike, and hire professionals for them, like a bookkeeper.

You could take 1 year, make and save as much as possible, then sell or close the business.

You could stop taking new customers, and wind it down while you get ready for law school, or another profession.

I recommend you work on deciding what you want, and identifying what you don't like about what you're doing. You may be able to accomplish your goals and stay self-employed, or you may find a new direction.
posted by theora55 at 11:12 AM on June 16, 2012

I concur with permiechickie, it sounds like it's time to hire someone to do some of the work.
posted by ob1quixote at 12:03 PM on June 16, 2012

This sounds like a dream job for a lot of people.

I suspect you may not be charging enough money. A friend runs a Mac help company and charges $150/hour and pays his 1-2 subs $75/hour. He loves his job. Another friend charges $300/hour and pays $150/hour to subs.

This is in Portland, OR. I feel like you must be able to charge way more in NYC.

Try getting a sub and seeing how that works out.
posted by MonsieurBon at 6:16 PM on June 16, 2012

Apprenticeships are made for this type of situation.
posted by moammargaret at 6:46 PM on June 16, 2012

We're all trained from an early age to see growth as an unmitigated good, especially when it comes to business; but to my way of thinking, having too much to do is every bit as bad as having too little. And it sounds to me as if your business, like mine, has grown to the point where you'd be happier if it wasn't eating quite so much of your time.

If you don't want to deal with the paperwork inherent in becoming an employer (which, speaking as a sole trader in the same line of work as you, I would not even begin to contemplate) then perhaps you can find somebody else in your neighborhood who is about where you were five years ago, and start deflecting some of your more angst-provoking clients in their direction? Maybe you could post an ad on craigslist.
posted by flabdablet at 8:35 PM on June 16, 2012

Also, in the alternative, consider raising your rates and cutting back your workload. Maybe a more normal schedule will ease some of the discomfort you feel now.
posted by mikewas at 6:10 PM on June 17, 2012

consider raising your rates and cutting back your workload

In my experience in a similar position, raising rates is doable but doesn't actually reduce business, and cutting back the workload actually involves sacking clients. But I have essentially good relationships with all my clients, and I don't want to see them stuck without support I know is competent. Which is why I've recently been so pleased to discover that one of my friends has just set himself up in a similar line of work - I can deflect people to him without feeling guilty, secure in the knowledge that he will look after them and will consult with me when he strikes stuff he hasn't tangled with before.

Businesses this small are all about interpersonal relationships. It's definitely worth building a good one with somebody who in normal business thinking would be considered a competitor.
posted by flabdablet at 8:32 PM on June 17, 2012

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