Our Story

Welcome to HowDoYou Guide!

A lot of people like stories, though. That’s what this page is. Our story.

I’ve had a lot of jobs and a lot of interests. I have that “deep dive fixation” personality, and I also love trying new things. I’m admittedly not the best at sticking with one thing for a very long time.

However, I’ve gotten very good at getting good at things. And also, at explaining things to people.

Or so I’ve been told.

I also like exploring and consolidating information. Making directories. Putting information where it’s easy to find.

I started writing some sketches, and some parts of it were rather good! Good enough to think about getting it published.

And I got to thinking, how am I going to sell the book? What is the endgame? Do I sell it to a publisher, then go back to bartending while maybe promoting it?

Or do I keep the rights to the book and self-publish? Do I use the book to start conversations and open doors to new and interesting things?

But…

What’s the business about?

What’s it for?

What do I call it?

I went through whole other jobs in whole other industries (recruiting, finance, tech) while letting the idea simmer and working on ideas for the book.

I looked for a name for a long time but nothing stuck. Probably because I didn’t know what I actually wanted to do with it.

I really enjoy the site McSweeney’s, and I love how they can write about pretty much anything, but you know it’s their writing, and it will have a certain style, opinion, humor to it.

I love the idea of having a name, a platform, a vibe, that’s flexible enough that I could pivot to whatever good idea struck me. To post guides and also directories and also maybe some opinions. Maybe.

But at this point it was really just a vague notion of “I want to do a thing” and “I’m working on a book.”

I could write all sorts of guides.

I’ve had all sorts of jobs and interests, and at those jobs I was usually the person who wrote things down.

I’ve done tech and music and recruiting and personal training. I’ve volunteered in construction and horticulture. I’ve poked around in politics. I’ve taken lots of train and transit trips. There’s so much I could write guides on.

And also I just really enjoy poking around and doing light research. And sometimes other people might benefit from it.

Today’s obvious solution to the “how do we pay our bills” problem is to become a content creator or influencer. But, you need to be constantly posting and curating a personal brand, and that’s just not my M.O. I want the things I make to be worthwhile in themselves.

I don’t want to make a content mill, constantly churning out fodder to grab people’s eyeballs so they stick around long enough to watch advertisements. I want to write things of quality. Things you could send to your friend, keep in your wallet, sit down and read, come back to.

So the influencer route is out. How do you make ends meet doing things of quality, in today’s economy, without just being a cog in the brainrot of social media and its really enticing advertising revenue?

I poked at this for a while.

My first thought was to sell actual physical guides, on paper. And for big guides, like the bartending book, that makes a lot of sense. But a book takes a long time to write, and what if it doesn’t sell? And what can I do right now?

I also thought of selling little guides, based on the things I wrote. How do you try a new cocktail? How do you ride transit in Chicago?

I wrote a “How To Try a New Cocktail” guide and printed it on folded business cards. It looked nice, but… well… I really couldn’t imagine people paying more than a quarter for it. If that. It felt more like a free promo.

So, small guides as a source of income? Probably not. Unless I can sell bundles of a couple thousand to a bar or liquor store or transit agency.

What can I sell, especially while I work on the book (a book that’s becoming a more daunting task as time goes by)?

Stickers!

• Stickers are relatively inexpensive to print.
• You can sell them for a few bucks.
• Unlike t-shirts (which I’ve sold before), everyone buys the same size.
• You can pack a couple thousand of them in your bag to sell at street fairs.
• Worst case scenario, if they don’t sell well, you can send them out as free promos to get people excited about a book.

I printed out a first run of stickers, and they turned out… better than I expected. Really pretty. I designed them while I was hanging out in a cafe and thought, why not do coffee stickers too?

So I did, and I got my first wholesale customer. You can find my coffee stickers on the shelves at Plug Coffee in NYC.

People are buying them! So I guess it’s a decent idea.

I also got a professional logo* and that made everything feel more… real.

Right now I’m working on several small guides and a couple big ones (the bartending book, and a transit guide). The smallest guides are just a simple business card with things like how to order coffee and how to take a train to the airport.

While I work on the big guides, I can hand out the free mini-guides, start conversation, get feedback (so I can write better and better guides over time), and maybe people buy stickers while they’re at it.

Our two main areas at the moment are Bartending and Transit. But you’ll see other stuff along the way. Job searching, politics, gym stuff, music…

We haven’t yet reached our final form.

There are like a hundred different directions we might go from here, and we’re feeling them out.

Each new thing we do, we’ll try it out, see what sticks, learn from it, and keep our eyes out for where it takes us.

Enjoy the guides, pick up some merch if you like it, and watch for what we get up to next!