I would really like to get out of the 9-5 "cubicle" existence and do something where I can work from home, take off when I like, etc. Don't get me wrong... I don't mind working hard, but I just am not enjoying the whole corporate thing where my hours, vacation days, dress code, place of work, etc. are set. I really think this is possible because other developers are somehow pulling this off. But so far it is just in the "dream" stage and I have no idea how to move it forward. I don't know if I want to be freelancer, start my own company or what.

In case it matters, I have been working in .Net / MVC for the past few years (both desktop and web) but have experience with other languages as well (Java, C++, Perl, etc.). I don't have much experience with "web design" side of things since in all my jobs other people have handled that while I have worked on the "programming" work.

Just to make it more concrete what I want... I wake up on a random Tuesday in June and it's a gorgeous day. I am ahead of schedule on my projects and I don't feel like working ... I want to go hiking. I want the freedom to do that without dealing with some PHB.

Another scenario... I do feel like working but I want to go visit an old friend or relative for a week in Bismarck / Budapest / Boston. Said friend has reliable Internet. Why can't I do that?

I'm not talking about being irresponsible just a bit more free.

  • I'm saying 5/6, so +1 – Matt Ellen Oct 6 '10 at 13:17

I feel your pain. I was in the exact same situation 12 years ago. I finally quit to become freelance and that where all started for me (now I own my businesses)!

Here is a very simple strategy (it's more a draft, I will be more than happy to discuss that with you by email). Steps are really simple to enumerate, but they are very hard to achieve. The difference between those who are successful and the others is that the later tend to quit when they face the first difficulties.

Your goal: leave your job to become freelance, create some slack in your life or be in a position where you can negociate better work conditions with your existing employer. I don't know what is good for you, since I don't know you.

  1. Eliminate waste in your life

    Those tv or magazine subscriptions you don't use very often, that new car that cost you so much, that big appartment you call "the cash drain", and so on. You must minimize the amount of money you need per month. This will be the key in later steps.

  2. Create a saving strategy

    Now you have minimized the amount of money you need, save the rest. The more you minimized and the more you earn, the faster you will be able to do the next steps. If you have debts, start to pay them first, then save.

  3. Be indispensable

    In your daily job, work hard. Do more than your assignments. Help your colleagues. Propose. Suggest. Question.

  4. Keep your word

    You have to become previsible in business. You say you will deliver A, deliver A, and even more. You say you will do B, do B! Simple, but more difficult that you think. The key is avoiding to give promise on things you will not be able to achieve.

  5. Quit

    When you have accumulated enought money to be able to stop working for at least a year, try something else. This can be a project you always wanted to do, another type of job, anything.

This is where I leave you...

Further reading:

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  • Congratulations on your business! +1 Solid strategy. – Ryan Hayes Oct 6 '10 at 14:28
  • +1 Good summary of the practical aspects of a change. If you cannot scale back and prepare yourself for "boom and bust" / "feast or famine" then you should not even consider going out on your own. If you scale down your needs and get out there with a solid reputation for doing what you say you will do you should be able to achieve your flexibility goals. – Todd Williamson Oct 6 '10 at 19:07
  • I guess that if you do steps 2,3 and 4 and really become an great asset for your company (really indispensable), you might also be able to then bargain a deal for them to let you work from home, and be able to skip stuff, and work in a goal-oriented way (they should know by know you are good at delivering your goals). I guess you'd have to be strong in this position, like either Quit or Work from home, and you have to be prepared enough to quit if they really dont want to (plus maybe when they see you are serious they will think it twice :P) – Francisco Noriega Oct 6 '10 at 20:37
  • I'm reading The 4 Hour Work Week right now. Some really good advice in there. Even if you're not interested in becoming an businessman per se, there's good tips for changing one's outlook to work, life, money, etc. – Bobby Tables Feb 1 '11 at 1:16
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    @Bobby: yes there are many good advices in the book. Some bad also, read the reviews on Amazon to learn more about that. – user2567 Feb 1 '11 at 7:08

I've only been a professional, paid developer for 4 and a bit years, but I've spent a lot of time wanting more time to do my own thing.

For my first year and a half I worked for one organisation. It was a good place to start. I had a great many experiences, including negotiating a (relatively) large increase in my salary, and moving across the country when the business migrated.

After 1.5 years in that job I got a call from a manager (I'll call him G) who had quit to go freelance, and wanted me along on his latest contract. The money was double what I was getting, and I was bored and frustrated in my current position (for many reason, mostly bureaucratic), so I took him up on his offer.

I set my self up as self employed, and started on the gravy train. At first I found things to be great. It was a contract at a company that was only 1 year old, so we had a lot of leeway, plus it was the same sort of company I had been working for before (and a lot of the same people, but that's another story), and I could work from home. This was important because the site of the contract was an hour and half away, and I didn't fancy a 3 hour round trip each day.

Unfortunately, after a few months, things started to go down hill. I had moved house again by this point, and I was closer to the customer site. Interaction between us (by us I mean the group of people that G had hired) and a couple of third parties that the customer was using were strained, and development was slipping. The customer was getting shirty with us (and everyone else) because they wanted to launch and their systems weren't up to scratch. I had to start coming in everyday - a 2 hour round trip. Requirements for our projects were spiralling out of control, and I was incredibly stressed. G had fired one contractor over a disagreement, and our morale was low.

After a few more months of this things levelled out, the customer got enough of what they wanted to launch on time. Things still weren't up to scratch, but work was steady instead of out of control.

At this point I was left doing something I found incredibly dull and boring. I carried on because I felt like I should finish what I started, also G was promising me more interesting work further down the line. I was still having to go on site everyday and this was having a negative impact on my home life.

Things didn't change in the sort term (a few months), so at 11 months of being self employed I told G that I was going to move on in 2 months, and try my hand at my own thing. I spent those months tying up loose ends and producing a lot of documentation.

I left, but a month later I was brought back in because G hadn't had time to find someone to replace me, and I'm not one to let people down. I carried on for 6 more months, after which I was replaced (thanks in no small part to my documentation).

I had earned a fair bit of money (possibly more than fair) so I set about working on my own project. This was going well, although it didn't pay anything. Due to my lack of income, my then partner (as in romance, not business) started to complain that I wasn't doing anything. She couldn't understand how I could work on something that (probably) wouldn't make me any money.

I promised her that I would find a job after 3 months working on this. So after I put my project into late alpha/early beta (where it's been for some time now, without real development), I stopped being self employed and got my self a salaried job.

I have been in this job for 4 months now, and I feel more free and happy than when I was freelance, even though I've gone back to the same salary I was on before I was freelance.

My hours are better, the commute is shorter, support from my manager and team is better. My work day is far more pleasant than it was in the 3.5 years before

I understand the desire to be more in control of your work day, but freelance doesn't always give you that, and it can make things worse, not only in your work life, but in your personal life.

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  • 1
    +1 great post! glad everything worked out in the end. Freelancing is often harder than it seems. But working from home in a corporate setting is the best of both worlds I think! – Spooks Mar 18 '11 at 20:31

Sorry for the length, but this is something I've thought about quite a bit.

You're going to have to sell this idea. I know, you don't like sales that's why you became a programmer. Welcome to the real world of how to get what you want.

You've identified what you want and that's a good thing. What are the objections to flex-time and working remotely (they are not the same thing)? Larger corporations have rules that were generated by committees to address these things and sometimes your supervisor cannot overcome them for you.

That leads us to your immediate supervisor. What are their views on this? She may have that "what if something goes wrong?" issue. Some situations require a developer to be on call to handle some level of support. Are you the only person available or can you work this out with a team and take turns. Obviously you have less flexibility when it's your turn. She may be OK with it, but gets pressure from other departments because they don't have the same privilage or it looks like they're letting you slack. You need to convince everyone that you are there when needed and get things done on time. An IT department that answers 'No' to every request and is late on all the others, will be percieved as never being around when you need them.

It is tough to get people to be more results oriented. After all, if you worked longer hours, you'd get more results. We know that is not true. Citrix has been involved with some research in this area.

You have to prove yourself to be trustworthy. Not a huge fan of the book 4-Hour-workweek on the whole, but there is an interesting chapter on managing flexibility even when you have a job. There is a progression you can go through to build on this. It's great that this is what you want, but what's in it for your employer? Are you willing to take less salary? Can you show that you actually more productive?

I mentioned that flex-time and working remotely are not the same. You don't want to be in a remote working situation, but are expected to keep specific hours. I was with a company for 3 years and moved away to a different time zone. I was able to work remotely, but would get phone calls after 6 (normally it was an 8-5 gig) because people forgot about the time change. We needed to discuss my keeping hours in the 'other' time zone or manage everyone's expectations and ability to do the math.

You may have more flexibility than you think and can work towards getting more. Start including this in your next review/salary negotiation. You may be entitled to a raise, but they can't afford it right now; ask for 2 days a week from home. There may be set amounts of vacation time, but that doesn't mean you can't utilize a 'time banking' system in your department. My biggest fear is staying up all night to solve a problem and not being able to come to work later in the day. Or worse, I am allowed to come in late, and everyone thinks it was personal time.

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