Editor’s Note: This is a guest article by Ali of Alpha Student ^[1] (gorgeous blog design).

Do you work for an employer? If so, you might have considered leaving to work for yourself instead. You might even be actively building up a source of income on the side – maybe through freelancing or through entrepreneurial work – and creating an escape plan.

I left my full-time job in technical support a couple of months ago, in order to further my small but growing freelance writing and website creation business, and to head back to university to study for an MA in Creative & Life Writing. The past two months have been the most productive and growth-filled that I’ve ever had. I encountered a few surprises along the way and, if you’re thinking about self-employment, you might want to read on…

(Those of you who are self-employed – read too! You’ll be able to nod and smile along with the things that surprised me, and I hope you’ll share your own experiences in the comments.)

Things You’ll Miss

Missing the Office Perks

The first surprise I had was finding that I occasionally miss working for an employer. This typically happens when:

• I have to buy tea/coffee/milk again – no bottomless office supplies now…
• I need some handy-dandy bit of software that I used to use for free on my lunch breaks before. I realize it would cost my entire monthly earnings to buy it. I spend ten hours attempting to do the same thing with open source solutions.

I regularly remind myself of the plus side, though. I might have to buy my own milk – but I can keep whatever food I like in the fridge without risking anyone nicking it. And although I have to buy or find software, I can install anything I like on my computer now.

(Since I’m in the UK, I don’t have to worry about those “minor” perks like health insurance that US residents need to take care of, which I’m frequently grateful for!)

Missing the Commute

If you regularly sit in your cubicle and fantasize about quitting your day job, one of the things you’re probably most looking forward to ditching is your commute. I used to cycle to work, though, and despite the rush-hour traffic, I found the half-hour bike ride at the start and end of the working day a great way to unwind. When I began working for myself, from home, I ended up feeling “stir crazy” if I didn’t set foot outside my flat before lunchtime.

I’ve partially solved this one now I’ve enrolled on my postgrad course by working in my university’s library; it’s a twenty-minute walk, and gives me that all-important barrier between work and home (as well as a dose of fresh-air to wake me up in the morning…)

Missing Having Colleagues

The more misogynistic amongst you might look forward to ditching not only the commute but also the colleagues that go along with a full-time job. You might be surprised, though, to find that you miss the day-to-day interaction with workmates. Even if conversations in the office rarely went beyond “Did you have a good weekend?”, realizing that you’ve not spoken to anyone except your housemate/partner/cat in the past 24 hours can be a bit depressing.

I took on a part-time childminding job for a bit of extra cash, and this proved the ideal solution: it meant getting out of the flat and talking to people (and kids are great fun to chat to – a constant source of energy and inspiration!)

So those are the things you might end up missing … how about the stuff that you’ll find yourself gaining?

Things You’ll Gain

Gaining Productivity

My major worry when I quit my job was that I’d suddenly end up bereft of purpose, spending my days slouched on the sofa in front of bad television. I worked efficiently at my job, but I can’t deny that keeping up with some of my blog-reading and personal-email-checking was done in idle moments on the clock… surely, working from home, with no manager lurking nearby, would mean giving in to the temptation to kick back and relax whenever I wanted?

It didn’t work out like that, though. I now find that I rarely check blogs or “fun” websites until the evening – though sometimes I’ll flick to them during a planned break in the day. I suppose I shouldn’t have been surprised by this: it’s much easier to stay on-task when you’re doing work that you’re passionate about.

Gaining Work

My other worry was that I’d not have enough work to do. When I left my job, my freelancing consisted of staff-writing for two blogs (a total of four posts per week), and a provisional agreement to create a website for someone I’d previously worked with. Not exactly a full week’s workload…

But from day one, the work started coming in. The person who wanted a website needed some proofreading; a couple of blogs I’d guest-posted on took me on as a staff-writer, a magazine editor emailed out of the blue (I’d been in contact weeks before and hadn’t heard back from her) to ask me to write an article. A friend who knew I was freelancing passed on details of someone she knew who wanted a website rewritten…

Again, I probably shouldn’t have been surprised: I’d been deliberately holding back on looking for more freelancing work while I was a full-time employee. There were opportunities out there all along, I’d just not tried reaching out for them before.

If you’re working for yourself, what surprised you about making the jump from employee to self-employed? If you’re an employee wanting to quit the day job, what are you worried about – and what do you think you might be surprised by?

Author bio: Ali is a freelance writer, blogger, website creator and postgraduate student. She’s also just launched Alpha Student ^[1], aimed at “helping students get the most from their time at university.”

If you’d like to write a guest post and get your message out there follow this link ^[2].

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