Learning to Self-Direct Your Work

There is sometimes really great value in certain kinds of peer pressure. For some of us, one of the greatest motivators to getting something done is the knowledge that someone else is counting on us. This is often one of the most motivating factors about conventional work environments, where you show up with the goal of doing your part as a member of a larger team.

But how do most people deal with this when they strike out on their own? There is a nice security blanket to be had in that outside pressure — it helps shove us out of bed in the morning, when what we may really want is to roll back over and sleep some more. And while most of us probably grumble about that (at least a little), once you are working alone, trying to build a solo business, there are days when that outside pressure is easy to miss.

WebWorkerDaily published an article on this very issue this week. In it, they identified five keys to success for self-directed work. When I review the list they’ve identified, I see, not only good advice, but many of the same things that I continue to struggle with as I proceed through this journey myself.

Secret #1 – Stay on Course
This one is hard, because it’s often too easy to be tempted by distraction — especially if that distraction comes in the form of paying client work. This is particularly challenging if part of your new professional efforts involve a career change or shift from your previous work. If the people in your network know you as a Marketing Manager, then it’s easy to be asked to join clients in that role, rather than build a new web design business.

Picking your direction is key, and then identifying steps you need to take to grow your business as well as the steps you need to meet your client needs will give you a list of tactical things to do. And I’ve found that it’s often much easier to stay focused if you can move from task-to-task with a clear understanding of why each is important and what bigger goal it ties back to. There is very little as satisfying as a To Do List with a ton of things crossed off!

Secret #2 -Overcome the Sense of Disconnection
This one is particularly hard for us extroverted types. I spent the first six months attempting to work from home and having it drive me out of my mind. For me, it was the single biggest hit to my sense of daily sanity and it took months to start finding a solution that was of value. The problem wasn’t with feeling disconnected in my work tasks, it was feeling socially disconnected from a lack of daily face-to-face interaction with colleagues.

Ultimately my solution for this was co-working. As a growing trend, co-working has proven a sanity saver for me. Co-working spaces come in all flavors, and exploring the different options in your community is probably necessary before you find one that is a right fit. But one of the most valueable changes for me over the past year has been finding a place where I can go each day to work, surrounded by other people who are working, where I can take a break, chat with other entrepreneurs, and kick around ideas that may have nothing to do with my own daily work. It’s the ‘water cooler’ effect, and until I started my own business, I had no idea how much my emotional health relied on that type of daily connection to other people.

Secret #3 – Learn to Live in Exile
Professionally speaking, breaking into a new space can be hard. Getting your foot in the right doors to start carving out a name for yourself takes time, tenacity and sometimes a fair share of creativity. The single biggest help I have experienced is networking — and by that, I do not necessarily mean the version that is easiest or comes most naturally to me (social networking), but in person, face-to-face, local community networking.

Finding professional associations, Meetup groups that focus on your area of expertise, and professional networking groups for small businesses is a great way to start building a name for yourself in your community. And while web workers do not necessarily need to work locally, it’s often valuable place to start. It’s also a great way to meet other people in your field locally, which I have found invaluable for collaboration opportunities, brainstorming, and building some economies of scale.

Secret #4 – Take Control
Not everyone is a detail person. For some of us, the details of contract negotiation, tax compliance, corporation regulations and bookkeeping are enough to make us run out and get a job at Starbucks. (Add me to that list.) The bottom line, though, is that this is just part of the deal. So, for those (like me) who have a mental Control+Alt+Delete moment just thinking about those type of things, the best solution is outsourcing.

An LLC has less overhead involved than a corporation; and finding a bookkeeper that you can work with, a lawyer you can trust, and a CPA with some good discipline can make the difference between success and failure. The fact is, no matter how good your outsourcing options are, though, in the end it is still your business and you still have to fight past the moment where your eyes glaze over and you mentally check out. You must understand what the professionals you employ are recommending to you and why: they may be the jockey, but you are the owner of the thoroughbred. If the horse breaks his leg, the jockey can go find another job, but you are the one who has to deal with a lame race horse. Let them be the experts, but don’t use that as an excuse to remain blissfully ignorant about those aspects of your business.

Secret #5 – Offer, Don’t Wait to Be Asked
In retail, this is called “upselling.” Amazon and Netflix have both done a great job over the years of honing this process: “We see that you were interested in this, and so we’d like to recommend that.” This is often important to do with clients. Part of your competative advantage is your expertise. Odds are, your client is not an expert in your field, so they are counting on you to identify opportunities that they wouldn’t know to ask for. If you are not doing this, then you are missing an enormous opportunity — for both yourself and your client.

The flip-side of this, of course, is to be professional, respectful and responsible about this. If you have a client who can barely pay your the bills as it is, then don’t offer them something that they are not in a position to do, unless you are willing and able to make special arrangements (delayed payment, a trade for services, etc.). When I have clients in this position, I will often highlight some possibilities, but let them know at what point in the future they will make the most sense. It gives me the opportunity to maintain a dialogue with them about it, but it also lets them know that I respect their current situation and understand that they have to prioritize their expenses.

All in all, WebWorkerDaily’s list is an important thing to consider if you are either looking to start a business or if you are struggling with some areas of your business. It’s easy to leap in and then later discover that some aspects are harder to handle than others. But it’s also helpful to recognize that some things just come with the territory. There may be techniques to help manage them a bit easier, but in the end, a new entrepreneur simply has to tackle things that an employee never has to worry about.

And while that might be discouraging for some people, for others, those types of differences can be the entire point to striking out on your own in the first place.

Alora Chistiakoff is an entrepreneur, blogger, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas.