Refactoring Your Career


Work in this web world of ours is ever-changing. No matter how much you love your cutting-edge job, it’s not likely that you’ll be doing precisely the same thing in five years: tools, trends, and technologies are all evolving quickly, and our careers have to evolve with them. If you don’t love your job, that’s all the more reason to change what you’re doing; with new opportunities ranging from blog consultant to search engine ad buyer out there, it’s nuts to stick around in a job you hate.

But most of us don’t have the luxury to take a year off at a time to learn new skills while the bills pile up. Like it or not, we need to keep working even while we change the work that we’re doing. Enter the software development practice of refactoring: making small changes to a program that already works to evolve it towards a more functional version without breaking the parts that are finished. Here’s a catalog of career refactorings you can apply to help move yourself towards your own vision of what you want to be doing next:

Ruthless Self-Criticism – Put this one under the heading of “prerequisites.” If you’re too busy to execute on any career refactoring strategies, take a step back. Your career eats eight hours a day (if you’re lucky) of your life. Are you really too busy to devote some time to making sure that major commitment is as optimal as it can be? Whether it’s bowling nights, two-hour lunches, or those weekend beach trips, there’s probably something you could forgo in the interest of workplace happiness. Yeah, it stinks. Welcome to adulthood.

20% Time – Derived from the well-known Google practice of giving developers 20% of their time to work on projects of their own choosing, this strategy involves deliberately using some of your own potentially billable hours to learn new skills instead. This sacrifices some income today for the security of staying on the cutting edge tomorrow. You can use the 20% time (which might be 10% or 30%, depending on how much learning you feel you need to do versus how much income you can afford to pass us) to attend conferences or courses, read, write code…anything that contributes to keeping your skills sharp. To make this work, you have to be honest with yourself and set aside a regular chunk of time (a day a week or a couple of hours a day) instead of pretending that five minutes here and there while you’re on hold add up to something significant.

Instant Expert – This one sounds impossible, but I know several developers and trainers who have gotten away with it. If you’ve identified frobifying web sites as your next area of focus, you just start letting contacts and potential clients know that you’re an expert in frobification. When the first contract to frobify a site comes in, it’s time to drop everything, read the relevant literature, and figure out how it’s done. Key skills: the ability to learn really, really quickly and the chutzpah and self-assurance to convince people that you know more than you actually do. Major pitfall: you’ll get caught. Remember, you can only lose your reputation once.

Paid to Learn – This is “Instant Expert” with an honest face. In the midst of a large job, you may realize that some technology you’re not quite familiar with looks perfect for part of the deliverable. Rather than subcontracting, cut a deal with your client: “Hey, based on some preliminary research I think we should use whizzle components for the registration site. But I haven’t worked with whizzle components yet. Tell you what, I’ll only charge you 65% of my regular rate for the time I spend working on the registration site.” This works best if you’ve already got a great relationship with the particular customer and they know you’re not interested in ripping them off. Be prepared to deal with concerns about a fallback plan in case the new technology turns out to have problems that you don’t know about yet.

Serial Moonlighting – Young and full of energy (or caffiene)? You can always go the traditional route and start job 2.0 on the side while you’re still working job 1.0 full time. When job 2.0 starts to take off, you quit job 1.0. A bit later, you can start job 3.0 on the side. Lather, rinse, repeat. On the plus side, you can make a bundle of money this way, because you’ll never have any time to spend it. On the minus side, well, you’ll never have any time to do anything else either. And if you’re in the “New Economy” you’ve got to be very, very careful about intellectual property issues to avoid getting fired or sued.

Eternal Student – Self-directed learning isn’t for everyone. If you’ve tried 20% Time and failed because you just don’t quite have the discipline, why not use the structure of a formal course to force yourself to learn new skills? Community college is the traditional route, but you don’t need to be traditional these days; there are plenty of distance learning opportunities on the net, or you can go completely cutting-edge and take a course in Second Life.

Potemkin Company – This one is less about acquiring new skills and more what to do with them after you’ve got them. Prince Grigori Alexandrovich Potemkin famously set up false-front villages to deceive Catherine II on her tour of the Crimea into thinking his colonizing efforts were already a grand success. With the availability of quick-print business cards, answering services, $6.95 domain name registrations, VOIP, outsourced graphics design, and so on, it’s pretty simple to build up something that looks like a company from the outside even if there’s not a bit of business on the inside. If you’re at the point in your career refactoring where you’re ready to do business, it can really build confidence (for both you and for potential clients) to do so as a corporate shell rather than as Joe, the guy down the street. Tip: get accounting and legal advice early to avoid costly mis-steps.

Patchwork Career – You don’t schedule a single meeting to take up an entire week; why should you schedule a single career to take up your entire life? Freelancers are used to juggling together jobs from multiple clients at one time. Extend that a bit and you can juggle together multiple types of work: writing, Web site design, PR, whatever catches your fancy. This makes refactoring just a natural part of the flow; when you spot an interesting new direction, you just add it to the mix, perhaps with a bit of 20% Time or Instant Expert. Watch out for becoming the living embodiment of “jack of all trades, master of none” though – and remember, four quarter-time jobs do not have the fringe benefits of a single full-time job.

Have you successfully refactored your own career to stay competitive? Have more strategies to add to this list? Tell us what works!



Excellent article. I can see how this applies to any career. Even in sales and marketing, there are always new things to learn, new products to learn about, and updated ways of approaching your profession. Sales in many cases turns out to be a “freelance” situation, which is also the preferred approach as opposed to working “in house”.

Paula G

Great article. As someone in the middle of the two jobs or more at once — starting a business (well 2) on the side while being prisoner to the cube by day, it takes juggling. The good news is over time it should pay off for a new career entirely. Life is too short to be stuck in jobs you hate.

Ruthless Self-Criticism and 20% time are right on the mark. Take time every day to move toward the change you wish to see and momentum will build and so will expertise. That is how I changed careers twice. And, the whole career thing is a distance run, not a sprint anyway.

Susan Kitchens

It seems to me that refactoring has been a constant, for me. Either that, or my skillset resembles several fingers in several different pies.

What I find daunting about the jumble is how to represent it to the world at large. I’ve found myself pausing uncomfortably when it comes to “elevator speech” time, tho “digital renaissance woman” seems to do the trick.

I don’t know if I need a Jedi Mind Trick to overcome this, but when seeking new gigs, when I see the call for someone with deep experience in realm T (and a resume to match), I hesitate. I’ve a peripatetic history in several disciplines, which does include experience in realm T.. as well as realm Q, R, S and U and W.


Random question: Are there any plans to offer a full feed for this blog? I personally find the partial feeds rather annoying and as a result I only learn a fraction of the information you share because I don’t want to have to click on every article just to see if it’s work reading and applicable to my situation.

In regard to the post, I’ve seen my career change as I’ve gradually narrowed down where my interests lie and how I like to work. Over the course of several years (and I’m still in the process) I’ve been able to make a huge turn in where my career was headed from a path that was simply profitable to one that is profitable AND profoundly interesting to me.

Dave Good

The question is what are you more afraid of? Are you more afraid of starving, or of failure? Can your spouse and children cope with the uncertainty? Going your own way is very appealing, when you sit down to the same old same old, knowing that the only way you move up, is either soemone dies, you mary the boss’s ugly daughter, or mass desertions begin to occur.
The downside, the ever looming fear of failure. What if we throw a party, and no one comes? How do you build a business, when you aren’t sure what business you are in?
Lots of questions, few answers. Y’all have plenty of good ideas though, and that is what it takes to make it to that ever elusive “next level”.


I’ve ended up going for the full re-write as opposed to refactoring. When you’re a WindowsNT engineer and then move to a full-out linux shop, and then also find you’re responsible for a ton more other things, it’s time to hit the books big-time. :)

It’s a ton of fun though. Learning all about promoting using Web 2.0 and I ended up buying about 12 books on various items from my Linux sysadmin “hat” to figuring out how to design better and tackle search engine marketing, as well as learn L. Ron Hubbards techniques on business management and marketing.

When your life is like Microsoft Word 6.0, it’s sometimes easier to do a complete re-write, than just try to re-factor and tweak.

Mike Gunderloy

Whoops, I left one out:

Walk the Plank – Having trouble carrying through on your career refactoring plans? Announce to the world that in three months’ time you’ll be ready to undertake contracts on some bold new technology. Use your blog, post comments on WWD, or just tell current clients about the new line of business. The sheer terror of a looming commitment can be a powerful motivator. For extra credit, give your boss three months’ notice that you’re quitting your job (but watch out that you don’t get replaced in two weeks as a precautionary measure).


This is an excellent posting. Well done. I firmly believe that ‘refactoring’ as well as many agile principles can be applied to life in general. I guess one could say that agile is a ‘way of life or thinking’ rather than just a development process (anti-process).

I’m preparing to go on my own and the one thing I will miss from being a perm employee ( other than shared-cost health benefits) is the ongoing training subsidies. I will admit that I would sometimes rather buy books than go to conferences ( and have pitched such proposals to managers who gladly accepted ).

I wish there was a ‘Contractor’s best-practices’ or a ‘Contractors survival guide’ somewhere ;)


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