Ask Prolly: How Did You Do It?


Ask Prolly: How Did You Do It?


I’m using this photo I took with my 35mm to introduce a new Ask Prolly post. Its significance is nothing more than to illustrate amount of time I get to spend on my bike as a result of my current job: this blog. I get so many emails from people asking “how did you do it?”, make this blog my job. A recent email from a reader asked this, after a long intro, which is very atypical. People usually ask how I get ads or something else irrelevant and catty. This email was different. And it’s something we can all identify with. How do you deal with a turning point in your life?

Check out more below.

Hello Prolly,

As I sit hear listening to the black keys I felt compelled to send you an email…

Let me preface by saying I check your blog almost every day and enjoy its aesthetic and the messages you represent. Part road, part fixie, part urban, etc… I enjoy the diversity. I have to admit, I don’t know a lot about you or where you came from, but I am assuming you blog full-time…?

I am currently at a crossroads in my life… I put all my eggs in one basket. I have been educating myself to prepare for medical school, but now face the dilemma of not being able to get accepted. My credentials just aren’t up to snuff, apparently. I just received my master’s in microbiology and have been searching for a job. However, something about finding a job in my field just doesn’t feel right at the moment. I want something more, I want to express myself, travel, create an artifact. I don’t want to join the rigamarole of a 40+ hour a week job. You seem to get the best of both worlds, you get to travel, hang with friends, and do what you love to do, but still get to support yourself by doing it. No strict hours. That appeals to me. I guess the long and short of it is this… how did you get your start in blogging and could you lend a fellow homo sapien some advice? Perhaps you know of some sources I could check out?

I consider myself to be creative and have decent skills with adobe, photography, etc… although my html skills are weaaak. I have friends that can help me with this, but I am not sure where to start. I’m sure you’re a busy guy and don’t have a lot of time for this, but anything you can throw my way would be much appreciated. I also realize that I need to pick a direction, find a niche. You did that with much success. How did you get to that point?

Either way I’ll keep reading your blog.


I replied to Jim with this:


Totally understood man. I went to Architecture school, graduated Chancellor’s list with thesis awards. Worked in construction in highschool / college, moved to NYC with an extended knowledge about high-end residential and highly conceptual work, had no problems landing a job. Worked at 3 offices over almost 8 years. Then the economy crashed and the arch. industry followed. I began the blog in 2006 and it’s stayed very much the same, content-wise. Alleycats, parties, architecture, bikes, etc. I use the tag line “Bikes, Music, Design and Bullshit” loosely but that’s what it’s about.

I used to wake up early, get a few posts in before heading into work, then check it and update it on my lunch break. I’d do the same at night. All I have ever done is post about what I’m interested in and I guess I hit a good niche. My first advertisers came in 2009 and since then, I’ve been building up a nice list of sponsors. Each and every one of them has really been a huge help over the years.

They’re the only reason I can afford my lifestyle. That and I moved the fuck otta NYC and its expensive overhead. Now I’m in Austin, where it’s cheap, warm year round and has just about every kind of riding you’d ever want. I try to wake up early most mornings, between 7 and 8am depending, schedule posts, go on a road ride, come home, work more and then go ride some more.

It’s safe to say that I’m one of the few people in the world with my job but it’s not easy coming to that point. Getting freelance gigs and being flown to events makes it even easier to scoop content.

My advice would be: hustle. Always be on the hustle. Do what you love and be humble about it. If you do start a blog, don’t expect instant gratification. Patience is key. Just like cycling, you’re not going to be able to climb the biggest hill or do a century without some form of training. You’ve gotta work for it. I see a lot of blogs get way too greedy within the first year of starting up. Self-promotion is one thing but to expect tons of free shit is corny. Don’t hit up companies asking for free shit, they’ll come to you if they like what they see. Don’t burn bridges, don’t over extend your welcome, etc. Just do what you love and do it well, people will follow.

Good luck!