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My top 10 favourites of being a freelance software developer

I decided to work for myself about 3 years ago (2013) when me and my wife decided to move to Nanaimo on Vancouver Island. It was far from being a clear cut decision. The factors were a mix of cost of living in uber expensive Vancouver, slower pace of life, easier access to child care, less pressure to both work full time… The one thing that was clear cut for me was that the technology sector in Nanaimo is small, very small, so I knew that contracting as a freelancer was my only reliable option for making a living. It took me about 1 year to really get things going, but I can say that it’s been a very enjoyable experience with some mistakes but I would say mostly positive wins. Instead of sharing war stories, which I might do in another post, I thought a good summary of my top 10s would be helpful to those thinking about freelancing or to peers doing it already looking to compare notes.

1. Autonomy & Feeling of Freedom

I say feeling because you’re not really free, you still have bills to pay and clients to service everyday, in fact a lot more clients as you’re now the only point of contact. But there’s something about running your own business that makes you feel free. If you have a client or project that doesn’t feel right, or just doesn’t make sense for both parties then you can end it and move on saving a potentially painful experience.

2. Business Expenses

Getting the right work station, computer, chair was always a bit of a painful process working for any company. Even companies with a budget for capital expenses, it always takes some time and effort to get the right stuff. Now it’s simple, if I need it I’ll buy it. If it’s too expensive than I plan for it, consider what’s needed income wise to make it happen and target the purchase. There’s no more fussing about what’s within budget, what another co-worker will think when I get a brand new screen, standing desk and they’ve been at the company x years longer than me. All that company political baggage is gone. I’m not saying it’s wrong for companies to have red tape on expenditures like this, totally makes sense, but it’s a nice benefit of freelancing that the red tape is under your control now.

3. Self Motivation

Self motivation is a challenge for a typical job, even when you’re passionate about it there will be that X year mark where you start to lose the desire or passion. Based on what I’ve heard, and my own experience it’s easy for the drive in a job to drop after the 3-5 year mark. I admit I’m a bit early to be saying this as I’m only in year 3 of running my business. But I don’t think the desire to run my own business will drop in the next few years or anytime soon because the connection to making a living is much closer when you’re freelancing. If I’m not making money or much I’m not eating or able to enjoy life as much, Also, the prospects of having to look for a steady job is not something I’m currently excited about, which in itself motivates me on a daily basis.

4. Customer Satisfaction

When you run your own business you have to be in constant contact with your customers. For my profession, as a software developer, this is not something that is normally a requirement so it’s been a nice refreshing change. While you do have to deal with the stresses that are normally shielded away by a manager, you also get to gain in the satisfaction that your good work makes clients happy. On the flip side, when you screw up it’s all on your shoulders.

5. Vacation + Family Time

This goes without saying that if you run your own operation you basically call the shots on vacation and time with family & friends. Of course I’m not making money while I’m vacation, so this needs to be banked into your rate, but I’ve been able to take 8-12 weeks per year of vacation. I’m a big fan of taking 1-2 solid vacations per year, and then spreading out a few days off throughout to extend weekends or recover from tough sprints from work.

6. Self Improvement

This is not something I would have expected when I moved to freelancing because of my increased physical isolation from peers. But in reality, I’ve had more time to focus on self improvement for a few reasons:

I buy books constantly because (2. Business Expenses) aren’t a blocker in this decision.
Projects are planned for a mix of quality and #gettingthingsdone #gtd. In a typical company, you have pressures to #gtd, and this leads to cutting corners and weakening your craft. In software development, this is a huge problem and while I can’t say I do everything right all the time, I’m doing the “right things” a lot more than I used to. For those in my field, that means I’m practicing TDD when reasonable, refactoring, using new frameworks when proven. The result is that I’m actaully getting better as a developer. It’s one thing to know what is the right thing to do, and another to practice it. In the past I always knew what was better, but rarely had the time to practice it because of unrealistic timelines. And it’s only with practice that you can improve your habits and yourself.
Time to learn: Related to the above, I allocate time to just learn and improve. Some companies do this, but it’s something I like scheduling for myself.

7. Breaking the 9-5 mentality

This is a pretty common one for freelancers who are single/unattached and travel the globe. For me, I don’t fit that mode, I have a family and young kids so I’m generally at home all the time. But that being said I don’t work the 9-5 everyday, if I’m not feeling the flow I’ll just stop and do something else. There isn’t as much of the must do 35-40 hours per week type mentality when you freelance. On the other hand, when you’re billing by the hour and provide some level of support during the day, then you come back full circle. It’s just different when you’re in charge, I find myself thinking about work in terms of productivity and value delivered to the client than making sure I work my 8 hours a day. I definitely don’t value a day by my hours and watch the clock. Well I do watch a clock, a Pomodoro timer that tells me every 25 minutes to get up and move.

8. Location & Flexibility

A lot of professions fit into the same category as software developer in terms of capital needs, a computer, wifi and a phone. I love the fact I can work from various locations, although I have been working from home almost 100% the past year. But as an example, I can drop my son off at his early preschool classes in the morning, go to a Starbucks and work for a 2 hours, pick him up and drop him off with family then continue work from home. These are things which are just a pain to deal with when you work for a company that has very specific requirements on when and where you work. I think the reality of 2 working parents is shifting the tide here in the corporate world, but I’m not sure it’s happening that much for SMBs.

9. Connecting with other Freelancers or businesses owners

I really like the fact I can just connect with other business owners and chat about work. Normally through co-working spaces, or coffee shops but and through online channels. This isn’t too unique to freelancing, but you don’t tend to be exposed to other businesses or networking on a daily basis unless you’re in management or sales.

10. New Business Opportunities

When you freelance, you open up new opportunities because you are basically a free agent. I think it goes without saying that if you’re working for a company as an employee, this isn’t really possible. While you can moonlight, it would be very difficult to join a company for equity and be serious & honest about both your job and the startup. As a freelancer, I’ve been able to join startups while running my own business. At some point one side will pull more than the other and sacrifices will have to be made, but in the interim I’m able to try new opportunities without making it an all or nothing type scenario.


Well that’s my current top 10 for 2016 on why I like freelancing. I’m sure it will change as the years go on. I should have prefaced that in order for any of this to work, having a steady client based is a requirement. Without that it goes without saying everything else falls to the way side and your first goal is really just finding leads and converting. For me, as lots of people would advise, it was key that I had built up some solid connections before I moved to freelancing. It has allowed me to focus on my work instead of constantly looking to acquire more potential customers. I’ll follow this up with a Top 10 least favourite things soon.

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