A Day Dream for a Day Job

The first time I ever talked to Peter was on the phone. He was interviewing me to work on a project already in development. I generally like interviews. It’s a chance to meet a new person, learn about what they do and show them what you’ve done. I was happy after talking to Peter. Not only because I was going to work with him, but from my answer to one of his first questions: “If you could do anything in life what would it be?”. I answered immediately: “I’m doing it”. Peter repeated my answer out loud. He was trying to come up with another question that would encourage me to be more descriptive. As we continued to talk, I realized Peter wasn’t only interested in my professional abilities, but was genuinely interested in my hopes and dreams.
In the Beginning…
Growing up I loved computers, learning new things, being outdoors and sports (like skiing, Mt. biking, and surfing). My love of computers turned into a love of software engineering and I wanted a life where I could progress as a engineer while working on fun projects with fun people, be heavily involved in my sports and learn new things.
After graduating from college I had some great jobs that helped progress my engineering skills, but the rest of my life was almost non-existent. I mostly just commuted to work and returned home very tired. Much of my time was spent doing work or recuperating from work, everything else was secondary. My life seemed horribly inefficient. I would go to work and work no matter what. Whether tired, stressed or burnt out - work, work, work. I despised this way of life, but it felt normal and maybe even respected. I began to get burnt out on life and software started to be a burden. So I decided to try something new.
Making the Change: Freelance
I moved from the bay area to Oregon with the plan of being a consultant. I did it without much research or thought of where I would find work. I was ready to make software a hobby if it didn’t work out. Being a flash/flex developer I immediately found that it was the right time to become a consultant. I have not yet gone looking for work and have been able to find great jobs from the contacts and friends I made while living in the bay area the last three years.
My life is very different now. I don’t commute (or drive anywhere) and I schedule 100% of my time. When it’s a nice day I can take a few hours and go for a bike ride or rock climbing. I can ski on the less crowded weekdays. I’ve started guitar lessons and took a marine biology class in Baja. I find that when I work, I am more focused and get much more done. And I love to work. I have to pull myself away from work to do other things, then pull myself away from other things to do work.
Living the Dream
When I told Peter I was living the life I dreamed, a chill ran down my spine. I still wasn’t sure if I would make enough money, find insurance or even how to make a proper invoice. Do I register a business name? Will I be able to communicate effectively remotely? Although these questions were stressful, I found the stress was insignificant compared to the excitement. I am having fun. Many things are new and unknown, but everything I am doing is in pursuit of a better lifestyle. Now that I’ve found a better lifestyle, my dreams have not stopped. They keep me going and doing new things. Here are few of them:
- Get Masters degree
- Teach
- Learn guitar
- Perform
- Complete Spice (personal software project)
- Win a XC bike race at expert level
- Climb Mt. Shasta in 4 hours
- Publish article
- Write a book
- Travel South America for 4 months (include lots of surfing)
- Climb a 5.13
- Surf all over the world
- Multi day big wall rock climbing trip
- Learn a new language
- …
Franky, if you have already made the leap, you know what I mean. For all of you with your toes on the precipice, peering hesitantly over the edge. Jump. It’s scary. It can be tough. But it is so worth it.


Aaron! Thank you so much for writing an article I couldn’t skim. No bullet points, no top tens… I’m refreshed! I was actually able to read something in paragraph form for the first time in what seems like months.
Great article - I really loved it. I’m living my dream, too, and often, when people talk about how hard and scary it is to go to freelancing, I wonder if I’m doing something wrong. “Maybe it shouldn’t be this easy. Maybe I’m forgetting something.” That sort of thing.
Thanks for showing people the good side of freelancing. It’s not all ramen noodles and having your heat cut off, people!
Excellent Post Aaron! It’s funny how cliche the whole “follow your dreams” thing sounded growing up, but when I compare what I’m doing now vs. what I was doing pre-freelancing (waiting tables) it’s really pretty exciting. The other great thing that you’ve pointed out is how freelancing truly opens up your ability to grow - you’ve listed getting a Masters degree on your “dreams” list, which is something that lots of people don’t even consider once they start the corporate ladder. I think this is one of the lesser thought about aspects of freelancing - so many people focus on the here and now “I can work when I want to” type benefits, when one of the most rewarding parts of what we do revolves around personal growth, diversifying one’s perspective, and taking on new risks that we’d otherwise not be able to consider. Thanks for the great article!
Aaron–what a beautiful post to get in my Google Reader the morning I quit my job to join the freelancing world. Your post is truly inspirational, and I took it as confirmation from the universe that I am indeed correct in making the leap. Thanks for the perfect post to start the first day of the rest of my life.
Best wishes to you, and keep up the good work!
Tiffany, you go girl!!! Congratulation and welcome. It really is better over here.
Glad you could come down and surf with us this last week Aaron. That late session was an excellent testimony to the day dream aspect of the day job, even if it did manifest in the form of night surfing…
Hi Aaron. It was awesome to read this. I meandered over from Naomi’s blog, and quit my corporate job on Friday. I was sick to death of the stress that wasn’t panning out to getting ahead, icky pay, and feeling like I was forgetting all the reasons I started working in the dot com world to begin with. The day job was quite literally sucking the joy out of the things I used to love and be so good at. I gave my two weeks’ notice, and the second my clients heard I’d have more hours, they started loading me up…it was like they were just waiting, and I had no idea!
I couldn’t have read this at a better time. So glad to hear the grass actually is greener.
Thanks for sharing.
To Susan:
I told you so.
Love, Naomi
Shane and Naomi–
thanks for the warm welcome. Not even a full day and I can’t believe how excited I am about the adventure that lies in store. Thanks again for your kind words of support!
Aaron, it sounds like I am following in your footsteps. Six months ago I also lived in California and was burning out from a programming job. Then I moved up to Oregon and decided to try my hand at consulting and custom software.
Fast forward to today and I am learning more every day than I learned in a month at my old job, meeting more people, and best of all… writing more software.
Thanks for all the great comments. Finding a community of motivated people also doing the consulting thing has been a huge help (not to mention keeping me surfing (the night session was awesome, thanks for the good times ;))
Aaron,
Thank you for your guidance and insights, reminds me that the young can share great wisdoms with those not as young!! I’m truly proud that you are doing exactly what you want with your life, that you are healthy, very active, and that you are my nephew! I will stay with my dream and move forward with such positive influences in my life.