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Ready For Launch: Preparing To Be Your Own Boss While Still An Employee

I’m now less than two months away from quitting my nice, safe 9-to-5 job and stumbling into the world of self-employment. You might think I’d be coasting along at my day job, waiting for Thanksgiving to get here, but I’m not. In fact, I believe I’m now working harder and providing more value to my employer than ever.

Why? Several reasons…


My employer has been good to me. I owe them my best as long as I’m working there.

I searched for employment in New Orleans for about six months back in 2007. Nobody would take me on. I was fresh out of college and didn’t have much experience, and any employer would have had to spend a few thousand dollars on an immigrant visa to hire me. I got turned away by virtually every web and graphic design company in town. Most of them liked my portfolio, but it was cheaper to hire local. I couldn’t argue with that.

But I kept searching, and eventually came across an open position at Loyola University. They took a chance on me, figuring I was a better fit than all the Americans who applied for the job. I’m eternally grateful for that opportunity, and I’ll continue working hard to reward their faith in me.

No regrets

I’m also working hard because I know I’ll come to regret it if I don’t. I’ve had previous jobs where I just coasted along and did the bare minimum to get by in my final weeks. That’s what everyone else did, so I did it, too. I was left with a bad taste in my mouth from those experiences though, especially when my former bosses would come through with great references for me. I felt like I had tricked them. They thought I was the bees knees but I knew I hadn’t given them my best. When you cheat someone like that and then they follow up with glowing praise, you can’t help but feel a little shitty.

One of my previous jobs was answering phones as a technical support agent at AOL in Ireland. Back then it was just a job to help pay my way through college. I would show up for work at evenings and weekends and do only what was expected of me, which wasn’t much. I would clock in, throw on a headset, take a few calls, help any customer who seemed nice, fob off the rest, welcome any distraction that came my way, then clock out and go home. My superiors liked me because I didn’t cause trouble and I cared a little more than most of my colleagues, but I doubt any of them remember me now.

Looking back, I’m aware of all the opportunities I missed out on at AOL. I could have gone into sales and worked on my selling skills. I could have gone into cancellations and learned how to turn irate customers into raving fans. I could have advanced to level 2 technical support and learned more about broadband technology. I could have applied to be a coach and built up some real-world leadership and management experience. Or I could have just stayed where I was but poured more of myself into the job, finding innovative ways to better serve more customers in less time.

At the time I’m sure I talked myself out of doing those things because AOL was just a paycheck to me. I didn’t really care about the company or the customers, and I didn’t see any point busting my ass for them. But what if I had? The same time would have passed anyway, but I’d be left with more skills and experience now. I thought I was looking out for number one (i.e. me) when I was taking it easy back then, but if I was really looking out for number one I would have taken advantage of every opportunity there and walked out much better equipped for life and business than I was when I walked in.

I’m determined not to let similar opportunities pass me by these last few months in my current job.

As you mean to go on

The last and perhaps most important reason why I’m working hard at a job I’ll soon be leaving, is because I believe in good work habits. Lots of people (like me at AOL) coast through jobs they don’t like just to collect a paycheck. They figure that they’ll someday find a job they love and then they’ll start working hard. But that’s like saying that you’ll only play hard when you make it to the NBA. The reality, of course, is that you need to play hard day in and day out to have any chance at making the NBA in the first place. The big leagues don’t owe you anything. You have to prove you belong there, and you do that by working as hard as you can at your job, no matter what it is.

Develop those good work habits, get better at solving problems, become remarkable at whatever it is that you do. Then you’ll be ready for your dream job when it comes along.

12 ways to prepare for self-employment while still an employee

So here are a few things I’ve been trying out. I believe these habits will serve me well when I leave 9-to-5 and start my own business. (Update: Yes, I realize these tips will not be relevant to everyone since we don’t all work in cubicles. No worries. Just take what you can use and leave the rest.)

  1. I don’t check e-mail until after 10am each morning. This ensures that I have at least two hours each day devoted to important (rather than urgent) work. It’s no coincidence that those first two hours of the day are usually my most productive.
  2. I’ve added a link to Effective E-mail Communication to my work e-mail signature, and every so often I’ll directly recommend that certain colleagues check it out.
  3. About six months ago I changed my outgoing voicemail message to say that I don’t regularly check my voicemail, and that people should e-mail me instead. Some folks persisted in leaving me voicemail anyway, so I stopped checking altogether. The new message light has been on for the past three months, but I don’t appear to have missed anything important yet.
  4. If I’m right in the middle of something and the phone rings, I try not to answer it. It’s a hard urge to resist and sometimes I feel like an asshole for ignoring it, but I’ve really bought into Jason Fried’s point about interruptions. I’ve also cut way back on the interruptions I cause for other people, opting to communicate almost entirely by e-mail rather than calling or dropping by unannounced.
  5. A note taped to my monitor: Am I being productive or just active? Am I inventing things to do to avoid the important?
  6. I track how I’m spending my time at work with RescueTime. The solo lite version is free.
  7. I have one big job list and one small job list. Everything I need to do goes on the big job list. Everything I need to do the next day goes on the small job list before I leave the office. That way I can hit the ground running every morning, rather than fumble about trying to figure out where to start.
  8. I ask myself every evening if I really gave it my all at work that day. Just stopping to ask this and evaluating yourself honestly is a powerful motivator to not suck.
  9. I ask “Why?” a lot more now. When a new work task comes along, my first question is whether it needs to be done at all. This isn’t out of laziness, but out of the realization that most tasks are created to keep people busy, not because they will result in something useful. The same goes for meetings. “Do you really need me in this meeting?”
  10. As much as possible, I try to devote a big chunk of time to each task and rip through it in one go. I’ve found that I’m much more effective if I can spend two uninterrupted hours on a task, rather than spending 30 minutes on it each day for 4 days. (UPDATE – You should totally watch this video: Jason Fried on why you can’t work at work)
  11. Not entirely related to work, but minimalism is also an important part of my preparations to become self-employed. Over the past five months, I’ve gotten rid of many personal possessions that didn’t provide much value in my life, and cut way back on my living expenses (turns out most of those are optional). As a result, I’m now saving an extra $1000 per month and I have a lot less crap distracting me from what I want to achieve. Most importantly, because I’ve learned to live way below my means, there’s much less pressure on me to earn huge sums of money right off the bat when I start my own business.
  12. I’m setting aside more and more time during the week for reading and study. I’ve been working my way through Chris Guillebeau’s AONC archives, checking out a few of Seth Godin’s books, and cyber-stalking several bloggers who have successfully made the leap to self-employment.

Your turn

Those are a few things I’ve been trying, but what about you? If you’ve already left Cubicle Nation and are off doing the self-employed thing, what am I missing here? For everyone else, what are your top tips for working effectively in an office environment? What work habits do you think would serve you well if you were to become self-employed?

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  1. Love your blog – this is the only useful information I found in a large search of “I don’t want to be at this job anymore” info.

  2. Hornets247 is still down sometimes, but still the best place for me to get to know the latest on the Hornets.

    Good for you if you have the discipline. That would really help you out.

    With your writing skills, you can no doubt find the perfect thing to write about. But yeah, there are plenty of e-books out there covering almost all subjects people are interested in. Just stick to what you know I guess and take it from there. The internet has this thing about going on tangents so who knows, the first branch you take to deviate from what you specializes in might be the one that would work. (I hope that makes sense.)

    I would also agree about clients being like bosses. So maybe that was the real reason why my attempt to work from home did not end up being as successful as I wanted to.

    Thanks by the way for accepting the Facebook friend request.

  3. Thanks for the comment, Bug. I hope you’re liking the updated Hornets247 πŸ™‚

    I’m pretty confident in my self-discipline, and I enjoy working hard on meaningful projects. I think the hardest part for me will be finding those meaningful projects. I have several ideas for products I could produce and sell online, but I think I’d be better served in the long run if I focus on my writing, and build some products (e.g. e-books or online courses) around that. But what exactly to write about? That will take some figuring out. It will have to be something that provides an insane amount of value to the reader.

    I won’t be doing much web design for other people. I’d rather try building my own websites with the potential to earn me passive income for a long time. Plus, I see clients as being kind of like bosses. You get to choose which clients to work with, sure, but then you have to do what they say and give them what they want or risk being fired. I’m looking for a little more freedom than that.

  4. First off, let me wish you all the best on your future plans Niall. Next, we’d surely miss you over at Hornets247. Although I’ve never participated much on discussions over there, I’ve made it my habit to read every latest post you guys have over there.

    You’re gonna need a lot of self-discipline if you are really serious about going the self-employed route. I’ve done it in the past with the whole SEO thing and the biggest problem I faced is the discipline to stick to a schedule. With no boss watching over my back, I tend to slack off a bit. Although I was able to work productively, I think my working habits were affected negatively by that shift…although it is still because of my lack of discipline. Haha

    By the way, what are you going to focus on? Web design?