Secrets of Successful Self-directed Work


We all know that working for yourself can be lonely, rewarding, challenging, exciting — and just plain hard. But if you haven’t worked for yourself before, and you’re considering it, it can be difficult to imagine exactly what it’ll actually be like. It can be even harder to understand what some of the lesser-discussed pitfalls of the process will actually mean to your daily schedule, your productivity and your attitude.

So what are these not-very-obvious challenges? These are the main hurdles I’ve faced and the tactics I used to get past them. But I’d also love to hear about how you’ve overcome self-directed work pitfalls in the comments.

Secret #1: Stay on Course

When you’re thinking in broad terms about starting your own business, your direction seems clear. You’re thinking “I’m going to develop and sell an app that…” or “I’m going to make designing marketing collateral my life!” and everything seems very clear cut.

Keep in mind, though, that no matter how driven you feel in those early days, as the weeks press on and you’re bogged down actually doing whatever it is you set out to achieve, you may find it increasingly hard to maintain momentum and direction. When you work for someone else, you have their demands to spur you onwards; when you work for yourself, you very swiftly become aware that you’re the only thing keeping you at your desk.

“Oh,” you say, “but I have a mortgage/child/holiday to finance. That’ll motivate me.” And it’s true … to a degree. But in reality, you could meet those expenses doing anything — you don’t have to meet them by working for yourself.

How will you maintain direction when you realize the only person keeping your train on the rails is yourself, and the journey could take a while? My preferred approach is not to let myself be daunted by the bigger picture: keep focused on the small steps, the little goals, and leave the bigger-picture-progress reviews for some other time — usually one I’ve set aside specifically  for longer-terms planning.

Secret #2: Overcome the Sense of Disconnection

Moving from a team work environment to a solo environment can be a big culture shock. Above all, as we’ve heard here many times, it can leave you with a pervasive sense of isolation. But as a corollary, you may feel as if you’re swimming around in your own little pond, rather than making a contribution to a larger objective. Instead of seeing yourself as a valuable part of a team, you can start to see yourself as being disconnected from the working world. And that’s all before you’ve had your morning coffee!

Over time, the WWD team has discussed a range of approaches to overcoming that sense of disconnection. I find that it helps to be strongly self-reliant, and to believe firmly in what you’re doing.

Developing a sense of self-reliance takes time, but it’s vital. I find that consciously focusing on my successes, reminding myself of my capabilities, seeking feedback on my output from clients, and keeping an eye firmly fixed on my plans for the future of my work are good ways to counter that feeling that I’m not contributing in the traditional way — that I’m not part of a team working toward a bigger goal.

These tactics also help to remind me of the reasons why I’m not working in an office for someone else, which reinforces my belief in what I do. And that gives me impetus to keep at it.

Secret #3: Learn to Live in Exile

As an individual trying to establish yourself in a new place within your industry, or within a whole new industry, town, field, or market space, you can find yourself feeling as if you’re on the outside of something, trying to get in. When you look at the big, shiny offices (or big shiny web sites) of the clients you want to land, you may well start to see an impervious wall rather than possibilities for opening doors.

The sense of exile can easily be exacerbated in the online space, as you fight to be heard above the hubbub of communication, or find yourself at the mercy of technology and distance. Is anyone listening? Does anyone even know who you are?

For some, the sense of exile won’t be a huge deal — many people who choose to do their own thing already prefer to fly solo. But there are others who feel it keenly. When I’m in that boat, I like to spend some time thinking about my client list and planning ways to either expand it or mine it further. I may also do something that I can only do because I’m not employed by someone else: take a few hours off at a moment’s notice, or change tasks to something that’s more fun or interesting, for example. This helps remind me of the positive aspects of exile, and makes it easier to live with the tougher elements.

Secret #4: Take Control

When you work for someone else, although you may be able to plan your time and tasks yourself, your work will, in some part at least, be dictated by someone else. The fact that employees don’t have complete control over their work is the reason for a lot of workplace whining, and in some workplaces this shared experience of restricted power is a crucial part of the glue that builds community and relationships among staff.

When you work for yourself, there comes a day when you realize that you need to take control of, and responsibility for, everything that happens in your work. By “work”, I mean work day, work tasks, work product, work planning, work schedule, work direction, work achievements, work partners … the list goes on. By “everything”, I mean everything.

Your business will thrive or fail on your efforts. It can be hard to get your heard around this, but you must. Accepting it — and full responsibility for whatever happens — doesn’t necessarily mean you need to become an overly driven, sales-focused bulldozer of a business owner overnight. What it does mean is that when you decide to take Friday off and go away for an impromptu long weekend, you’ll make sure you know — and are comfortable with — what that means for your workload, your clients, and your budget.

Accepting responsibility and taking control are actually great motivators that can help you overcome several of the challenges we’ve already covered, including disconnection and maintaining direction, as well as helping boost that good, old-fashioned key to success: motivation.

Secret #5: Offer, Don’t Wait to Be Asked

In a company workplace, you’ll usually have a nicely defined job with clearcut responsibilities. When your colleagues need something done that’s in your line of work, they’ll come to you and ask, or have your boss put it on your task list.

But if you’re on your own, that expectation needs to shift. Instead of having people come to you, you’ll need to offer yourself to people. You can call this “selling yourself” if you like; I prefer to think of it as offering my services. The point is that when you work for yourself, the focus will likely move from receiving work requests to actively creating work. Moreover, you probably won’t be eager to take just any work at all; you’ll want the right kind of work that suits your business direction, your capabilities and interests, and your goals.

When I started working entirely for myself, I quickly realized that any slowdown in my offers to potential clients would coincide with an increased sense of disconnection and exile, and sometimes, a questioning of my direction. The more I work to match my offers to clients’ needs, the more focused, involved, and valued I feel. Offers lead to work, which leads (in most cases!) to success — the one thing every business owner desires.

These are the five key challenges I’ve experienced since I’ve been working for myself. What challenges have you faced, and how did you overcome them?



Great Article, its really a challenge to start everything all alone but like all big guns say “hard work never goes unpaid”

Aboriginal Art Gallery

Really great article…
Thanks for sharing nice ideas and tips for self directed work. Your business need to work hard and complete competitor and market analysis.


The biggest hurdle I face is time management. Keeping myself on task can be tricky, but I like that the hours I work now actually fit my personality versus trying to adapt to traditional hours.

Great suggestion about presenting yourself to someone instead of waiting. That is an area I need to pursue more.

Good read.

Dan Sanchez

It’s incredible how simple these facts are, but how difficult they can be once we are faced with them. Great post!


Tim Dockins


I have found several parallels between the challenges experienced by the daily web worker and those of the daily academia worker (aka researcher/PhD student), but this article really hits home. While I haven’t started my dissertation yet, I realized recently that the challenges you presented in these secrets were some of the hurdles I’d have to face if I wanted to work in academic research.

So, thanks for the article!


John Stringfellow


Thanks for the great article. Your perspective on working at home and for yourself was refreshing and comforting. It is good to know that I’m not the only one that deals with these feelings of isolation. Your advice for dealing with these challenges is priceless.

Your article made my day!



Agreed, working for yourself is harder than you can imagine. Master these points and you are well on your way.

Executive Cars

Nice post about the self directed worked tips. This is too time consuming way of work. It take 100% consideration and take much time to look after the whole business.

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