A Little About Me

I have always been a dreamer, never a doer.

In middle school I would jump around my room lip syncing angsty alternative rock songs (Taking Back Sunday, The Used, Brand New, etc.) while pretending to play the guitar I begged my parents for. Sometimes I’d take pictures of myself jumping off the drum kit I didn’t play or come up with band names for music that didn’t exist.

I had album covers, music video ideas, and theoretical shoe deals for my side gig as a professional basketball player. Unsurprisingly, I never made it as a rock star or an NBA legend (side note: I’m 5’6″).  With all my imagining, I never learned how to actually create things.

See, I’ve always been one of those people who dreams well, but lacked the follow through to finish anything. And while I think that imagination is an important tool for developing creativity, there does come a point where you have to actually make some stuff—it’s part of growing up I think.

Eventually, and this is a harsh reality, no one cares what you’re ‘going to do when you grow up’ because you’ve already kind of grown up. At first it’s scary, then it’s depressing, but most recently I’ve found it to be kind of exciting.

Cue ‘How to 20something’

I had the idea for this website after reading a tweet by my friend Abby who suggested that she would write a book about how to survive her quarter life crisis once she had successfully made it to the other side. I resonate with that because I think there are a lot of people, myself included, who feel like growing up is mostly just stumbling around.

I think that the 20s are a challenging time of personal growth because our pre-adulthood aspirations run up against the post college realities and potential doesn’t really mean anything anymore.

All of a sudden, no one cares what we’re going to do when we grow up.

So it just makes sense to me that there should be a resource of like minded millennials (don’t ya just vomit when you read that word?!) sharing their stories about the process. If you’d like to know more about us, check out the “About Us” page here.

Here are the steps I took to stop dreaming and actually build this thing: 

Step 1: Figure out what motivates you 

Personally, I care very deeply about what my friends think of me. Knowing that, I met with all of the potential writers for this website individually and told them about my plan and asked if they wanted to be a part of it. Most said yes and after they did, I committed to a timeline I really wasn’t sure I could accomplish. Then, when we met as a group I further overcommitted by telling them that I would have the website ready in a matter of weeks.

So I was motivated to follow through because I had attached my reputation to my deliverables. Had I not met my timelines, I would have looked like an idiot to the team who had committed to the project and following through for them was extremely motivating to me.

Pro Tip: The two biggest motivational factors for me are not letting people down and not losing money. More on that to come. 

Step 2: Get Skin in the Game 

After settling on the idea of building this website, I had about 2-3 weeks of intense desire to make it happen. During those weeks I ran the idea past several of my good friends in an attempt to verify that I wasn’t insane and that there was a chance it could work. Overwhelmingly, people said I should go for it—that they would actually read and enjoy writing about this specific phase of life.

So I bought the domain and a year long hosting plan. 

My wife, Brittany, was none too pleased about my seemingly sporadic purchase and I can’t say I blame her, but I knew it was something I had to do. By spending the couple hundred dollars it took to get everything setup on Squarespace, I forced myself into action because once again, I’d look like an idiot if I didn’t follow through. Maybe the title of this post should have been “shame your way to productivity.”

The money component has been really important because honestly, there were plenty of days when I would have rather played video games than work on this website. I’m not saying it’s always financial, but my experience with this website suggests spending some money on an idea is a really good way to make yourself follow through.

Step 3: Seek out accountability 

At this point in our story, I’ve paid for the website (a couple hundred dollars), created the bones of the website, paid for the logo (more hundreds of dollars), had a bunch of writers over to our apartment for sink beers (like regular beers, but chilled in the sink), and created a timeline for launch. Let me be honest here—this is the point in the story when the shine of a cool new idea really starts to wear off.

I’ve been working on this idea for months and to this point, had very little to show for it. I needed accountability from people outside the project. Otherwise, I was destined to let the idea fade into the abyss.

So I joined a mastermind group with some buddies who are all entrepreneurs in different industries. Once a week we meet up and talk about our goals for the week over beers (not sink beers, normal restaurant style beers). We also text each other every morning at 6 am to verify that we’re awake and working. If we aren’t, then we owe each member of the group $10. Once again, skin in the game.

As of this writing, I’ve only overslept once. I’ll probably write about this process soon because waking up early has really changed my life.

Where We’re At Now

How to 20something represents something very special to me. It’s been a project that’s taught me that big projects are sometimes just a bunch of little projects tangled up. Once you start untangling, it gets easier to pull apart the weight of it all.

I hope you can learn a bit from my journey and I hope you come back here often to learn from our other writers’ experiences. They’re really great people and I can’t wait for you to see what they’ve written.

Also, please feel free to leave us notes in the comments about this post or the direction of the website. We’re still trying to figure this whole thing out and we’d love to hear your thoughts. Also also, if you’re interested in writing for us, check out this page. We’re always accepting submissions, though we can’t guarantee all writers will get published on the site.