one-on-one interview | jake olefsky

What would you like to tell us about yourself?

I never know how to answer open-ended questions like this. I’ll just let my answers to the following questions tell you about myself.

What is your profession?

This is a little hard to describe. Anytime I have to fill out my profession on a form I always end up writing something different. I have written: programmer, engineer, webmaster, website designer, website inventor, consultant. I wish there was one word that encompassed all of that, because whenever people ask me what I do, I never know what to say. In a sentence, I invent websites, build them and operate them.

What are the benefits and challenges of being self-employed?

The biggest benefit has got to be setting my own hours and not reporting to anyone. I get to work on what I want, when I want and I can take as much vacation as I want. I never enjoyed being told what to do, so working for myself has made “work” much more enjoyable. I actually enjoy work.

The thing I miss the most is collaboration with co-workers. It can get lonely working by yourself.

How do you stay current in your industry? What are you favorite professional resources?

I read all the daily tech news (techcrunch, slashdot, engadget, etc). Everything I do is documented on the web, so it’s pretty easy to stay up to date. I’ve always been a self-learner, so its easy for me to stay current.

Do you have a process for evaluating potential clients or projects?

I don’t take clients, so for me it’s just about what projects I want to work on. Whenever I get an idea, I put it into my logbook. When I want to do some work, I just scan through the list until something sounds fun, and then I do it. There are some things on the list that I will never do, and that’s ok. At least I captured the idea and can continue to evaluate it. Maybe someday it will sound like a fun thing to do. I try very hard to only work on things that are fun.

Can you describe your typical workday?

The first thing I do is answer all my messages. This includes emails, trouble tickets and messages posted on my websites. This takes several hours and is the most boring part of my day so I get it out of the way first. Then I read the tech news. Then I get to work. Hopefully this is before lunch. The rest of the day is spent working on my sites, programming in some way or another.

What tips can you give the Cyber Shy wanting to launch an on-line business or professional presence?

My two pieces of advice would be to do proper market research and know when to hire help. Often I see people trying to build an online business in a very crowded marketplace. If you have dozens of competitors before you even start, it’s going to be difficult. Try to find a niche that isn’t well served.

The other thing I see people doing is trying to do everything themselves without the proper training. Building a successful website takes a lot of different skills and years of experience. Instead of buying that “HTML in 11 Days” book, it would be better to hire a web designer.

Is there anything else you’d like to share with us?

Another open-ended question. Hmmm. I might as well shamelessly plug my websites. Visit for brain teasers, puzzles and game. Visit to organize your life with a powerful to-do list.

Jake's success is impressive and it's clear that he is doing something right. Here is what I am doing to follow suit.

I am logging my ideas for Thumbprint. I make notes of my ideas so that I can evaluate their feasibility immediately. [ Is there a customer for this service/product? Does bringing this idea to market line up with my brand values?] I know that, in the past, I have prematurely squashed ideas never to remember the initial inspiration again.

Being a power organizer in my professional life is something I am good at. However, striking out on my own has required me to put more thought into how I own and operate my small business. In order to maintain mobility and flexibility sans smart phone, I have begun migrating away from Microsoft Office for managing my e-mail account, calendar, contacts, projects, etc. To this end, I signed up for Toodledo. What's even better is that I was able to add Toodledo access to my Thumbprint iGoogle homepage. Organization, activate!

Thank you, Jake! We appreciate your time, all around web savviness and advice!

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