All posts tagged relationships

Momma Montessori


My parents put me into a Montessori school right off the bat.

I’m pretty sure they couldn’t afford it, honestly, but both of my parents came from backgrounds that emphasized education. College was a must. Intellect was a stated goal when raising children.

When we transplanted to Chicago and out of the “East Coast System” I think that paying for Montessori was partly a selfish parental attempt to prove they weren’t the ones with the dumb country kids amongst a litany of thirty-odd brilliant ivy-league-destined cousins.

The truth though?

It was mostly a belief in a non-traditional way of developing young minds. In 1986, no less.

It shaped me.

Learning to learn in the way that Montessori teaches you to learn had a profound influence on the way my mind works.


I remember learning French before I could read.

I remember my teacher pulling me aside one day and saying it was time to see if I was ready to read a chapter book.


I was the first in class to do this (or my 7 year old self I thought I was)…and I remember being proud. Even prouder when we were done and she bursted out with “you just read a chapter book!”

We took care of animals and learned math with our hands and had to clean up after lunch and snack time. Our days were spent solving puzzles and moving on to harder puzzles at the pace that made sense for each of us.


Montessori people can be spotted.

Their minds explore…and they have a refreshingly calm sense of the way their own mind works.


Mom began teaching. At the Montessori school they sent me to. The one I don’t think they could afford.

Momma dove into educating children The Montessori Way because she was a true believer.  She was setting little humans up to be great humans. She was also making it more affordable to give her son and two daughters the Montessori experience.

She’d have done road construction to make that kind of thing happen for us three.


Momma’s a child-whisperer. Momma turns kids into Rocket Ships of Goodness.

Today she runs the school that started me down my intellectual path. Down my emotional path.

Down the path that made me who I am today.

For two decades she’s given the gift I sit here and appreciate in a deeper way than I could ever articulate to thousands of children.

I know she doesn’t think her heart has room for anyone else when she thinks about me and my two sisters, but she’s wrong.

Her legend is in her capacity to deeply care about every single child that she has ever set eyes on, ever.

Her legend is how she makes her children the luckiest people in the world.

Our mother has the biggest heart.

We win.

My mother should raise the planet, from where I’m standing.


Tell me something about your mom?


Social Love, from Inspiring People

I’m not sure what this is.

I think I was pondering what became my About page and I realized I wanted someone else to write it.

So I asked them to.

A few months back I sent an email to a group of people I feel lucky to know. People from my past and present who have shaped me. People who inspire me, and people who are my foundation. People who make me laugh, people I’ve worked with…people I’ve dated.

Not everyone I emailed replied, which I expected, because when you read the email I sent them I’d imagine that a few were kind of confused or uncomfortable…

…how often do you ask people what they think of you?

It’s a raw thing to do.

The email:

I thought it’d be fun to set up a piece of my blog to represent the people I really dig, and their thoughts on my projects and writing. It’s narcissism on the surface, for sure, but it’s also my attempt to represent the breath of community I feel when I walk around various cities and spend time on the web. Some of you are bloggers, IRL friends, colleagues, or partners. I sent this to a list of people I respect and really treasure knowing.

Every person on this email is someone I’ve watched do something I’m impressed by.

Feel free to ignore. 🙂


They knew I might post what they sent me, so on some level this stuff is ‘best behavior’ kind of stuff when it comes to Who I Am; I know being a friend, family, colleague or lover to me isn’t always easy.

It’s not easy, actually.

Nevertheless, here it is, and it’s now my About Me Too page.

Below is a sample…check out this for more.

“Oh goodness where do I begin. I guess 21 years ago when I met you. Over the years you’ve been a constant source of love and amusement, a sounding board for my thoughts and questions, a politics/technology/social media bantering partner-in-good-fun and a run-the-streets-get-in-trouble-music-loving partner-in-crime. You are always the first to support and encourage your friends to live their best life and now you are living yours. You are very, very smart. Smarter than I think you let most people know…even me. You are a great dancer…I think one time some peeps mistook us for a professional dance troupe as we grooved our way into 2am. You are brave for so many reasons and I admire you. Our memories run deep and my love for you even deeper. You are my brother and my friend and our spirits will always dance.”

– Chalise, a garden fox and emotional genius, who is a best friend, sounding board, and spiritual sister –

“Dshan, I have so much love for you. You’ve got this ease about you, this way of putting your whole self and heart into the world, digitally and offline. I enjoy your laugh and your warmth. Thank you for sharing it as you do.”

– Gwen Bell – thought leader and author of Digital Warriors, who is in many ways a digital sherpa for me –

“I started reading Derek’s blog before I even really knew what a blog was. Years have gone by, and I still anxiously await each of his posts. His writing style is simple and moving; he writes at the heart of life. One of the sharpest ideafreaks I’ve ever met, Derek is a continual source of inspiration for me.”

– Nicole Antoinette, blogger and owner Shatterboxx Media, who is such a stupidly great writer and thinker that it makes me jealous often – –


There is more. Click here.


Make A Decision To Decide

Working on a web startup teaches you how to live deliberately.

It’s about making decisions quickly and taking action as a default, rather than the other way around.

It’s uncomfortable at first, in that it’s a deliberate way of being and until you live deliberately, you just don’t know what it’s like to do so.

You see the world differently in that you see it as one possibility after another, and you begin to challenge your own assumptions because you’re spending so much of your time trying to challenge the expectations of other people.

When you don’t take anything for granted and you decide to decide, you stop letting fear be an excuse to put the world off.

It doesn’t mean you’re not afraid to be wrong but it does mean you stop being afraid to fail.

Failing is actually something you realize everyone is doing, all the time, in small and big ways…and not only are you not judging them for it but you notice that the happiest people you know fail hard and fail often. The most successful people you know fail hard and fail often.

The people deepest in love fail hard and fail often, together.

When you stop being afraid to fail, and you decide to make deciding and doing your default, you also quickly realize that a lot of people are stuck.

They’re in a relationship they won’t decide about.

They’re in a job or career they won’t decide about.

They’re internally undecided about who they are.

Which becomes who they are.

You need to realize you’ll probably be wrong, but you won’t know until you decide and do. You need to know that waiting isn’t going to change things…and the things that do change while we wait are happening to us.

Letting things happen to you is very different than making thing happen to you. Making things happen to you is…well…

…well, it’s just better.

It makes you confident, and comfortable with a world you can’t predict. It makes it easier to know who you are, and to be who you are.

It becomes easy to talk about who you are, how you’re feeling, and what you’re doing.

It’s hard, too, so I get why so many people can’t break through the skin of their comfort zone to move forward. They can’t get into the habit of making a decision and taking some action, however big or small it may be, knowing that failure and missteps aren’t just unavoidable; they should be sought out.

That those missteps will be exactly what will make them happy or successful in the end.

I’m not on a pedestal.

I get stuck. I catch myself not deciding sometimes.

When I do catch myself though…I decide to decide and to do something.

You should too.

Image mine, bracelet & note courtesy of Emma, @maurer‘s daughter.

Loving Again And Again

We all have the potential to fall in love a thousand times in our lifetime. It’s easy. The first girl I ever loved was someone I knew in sixth grade. Her name was Missy; we talked about horses. The last girl I love will be someone I haven’t even met yet, probably. They all count. But there are certain people you love who do something else; they define how you classify what love is supposed to feel like. These are the most important people in your life, and you’ll meet maybe four or five of these people over the span of 80 years. But there’s still one more tier to all this; there is always one person you love who becomes that definition. It usually happens retrospectively, but it happens eventually. This is the person who unknowingly sets the template for what you will always love about other people, even if some of these loveable qualities are self-destructive and unreasonable. The person who defines your understanding of love is not inherently different than anyone else, and they’re often just the person you happen to meet the first time you really, really, want to love someone. But that person still wins. They win, and you lose. Because for the rest of your life, they will control how you feel about everyone else.

Killing Yourself to Live: 85% of a True Story by Chuck Klosterman

I love this, despite wholeheartedly disagreeing with Chuck’s conclusion that there’s a winner here. There’s no control forfeited to your template person, and I’m not even sure the person who shapes your perception of love is all that responsible for anything but their (hopefully) admirable qualities…the rest is time, place, and your internal self.

More than once I’ve tried to articulate something like this to someone who’s either never been in love or thinks that real love is only real if it lasts forever and supersedes any other relationship you have in the future…as if falling in love is only proven by its permanence.

It feels to me like a combination of fears, this perspective. Fear that this idea of love allows for the love you have today (or might have tomorrow) to fall short of forever. Fear that your standards for love should be so high that only one experience should ultimately meet them, and the resulting fear that the only way to recognize and defend the one you want to last is to make (and attempt to live by) a cosmic ultimatum.

There’s nothing unromantic about the idea that you have and will love more than one person in your life. It doesn’t undermine your chances at that forever thing…it doesn’t undermine your forever thing if you have it today. Chewing on this also lets you release your past with people, shedding that lingering ‘maybe‘ about exes in favor of you, today.

It’s also helpful, I think…the battle of love is a tough one, and at times it can seem like one of life’s cruelest illusions.

At times it can seem like a drug you can’t quit.

At times it just works, and seems like the fresh air you’re breathing as you navigate your life…an ether of support and happiness blanketing your world. I think the point is that you can trust the good and the bad…breathe deeply at both ends of the spectrum and know it’s all part of the process that doesn’t have to be black or white, one or none…

The people who shape your perception of love are your heart’s teachers. Letting them go is hard. Seeing how important they were shouldn’t be.


Find Me On Ophelia’s Webb Today

I was flattered to be a part of Ophelia’s Webb’s Pas de Deux Series and my post is up today, if you’re interested in another word vomit about love and whatnot. Seriously, this blog is a teacup full of emo lately. It’s like watching the Bachelor, but only the part where they interview him and he’s like “Gosh, love is so hard!”.

Anyway, a slice of the post:

I’m too much of a romantic or something. Maybe I just don’t like being wrong. I guess no one likes being wrong, but when things fell apart recently I think the hardest part for me was that the goodness didn’t win out.

That goodness is always what draws me in. It’s gotta be really special, you know? Special in a way that it seems crazy not to run at the world together, no matter how improbable that seems on paper. A goodness that seems more important than any hiccups or challenges could be, now or tomorrow.

So you take a dive.

Check it out here, and check out the perspectives on Love here.

Lightning Bolts Revisited

I sent flowers to a girl a lot of you know and plenty more of you have been curious about since I wrote about her shortly after we met for the first time. It’s pretty obvious I ended up caring about her deeply, although it really surprised me how many people invested themselves in the whole thing. Holiday reunions were peppered with questions and curiosity. I still get emails about that post, and in some ways it’s been tough to figure out how to share it all with people.

If you know her or if you simply read her last few blog posts, you’ll see the damage of her last relationship right on the surface and you’ll see a girl who didn’t deserve what happened to her…a girl trying to find whatever it is we find when our world gets torn apart and we’re left gasping for air.

You’ll see a gorgeous girl with a face-melting ability to write beautifully about her pain and confusion…a girl who falls asleep and wakes up with her heart beating so hard she can’t ignore it. A girl you want to sing about you.

I’ve struggled writing this post, mostly because I feel like I need to paint a picture we can both live with online, which is exactly how I said I’d never write. Fuck convention and forget what people want…write at the truth.

She had her world ripped away from her, and she’s just starting to surface with an idea as to how she might survive in a jungle she doesn’t recognize without him on her arm, without their projects as her projects, without someone who’s shaped her definition of true love.

It made her dangerous. We both knew it. I knew it. And I saw something in her that was worth the risk. I saw a goodness in her that I couldn’t and wouldn’t ignore. We talked all day and into the night, and for stretches that’s really all we had; I live here and she’s there. We agreed not to ask too much of it all, and to do our best to be open and honest and real…I still believe that’s the only way something meaningful emerges with a strong foundation.

And we had a pretty solid foundation, all things considered. We saw each other when we could, opened the lid on her pain and fears, sifted through my own fears and faults. She’s nothing if she’s not forthcoming, and she challenged me to be that way, which I want to be better at.

“You craft your thoughts…you say shit perfect. Stop doing that. Say it while you’re feeling it.”

There was the distance. The breakup. The room she asked for, to breathe and to grieve and to stand up without weights on her shoulders…it wasn’t easy to give her that but it was fair for her to ask. I gave her too much room at times, I think, and while she knows she did and said things that really hurt me, she did and said them from behind emotionally scarred walls. The distance made it all seem improbable, something I didn’t care about but also underestimated. Finding our foothold proved tough, aside from those moments when we were together in person and things were pretty great.

There were a lot of times when she wanted us to be an ‘us’.

I know that. She knows I felt that way too. In a different life, at a different time, that’s likely what I’d be blogging about right now.

In the end, though, things didn’t work out and when I last left Boulder I did so knowing it was time to actually walk away.

Walking away isn’t something I’m used to doing.

I operate from a deeply romantic stance on the world, maybe to a fault. Distance and circumstance seem to fade away in the face of an undefinable goodness that I like to think I have a decent sense for…a goodness I wait for instead of chasing it, and a goodness I don’t hesitate to chase when I feel it. It doesn’t happen often.

It saddens me, pulling my heart off the table and admitting some degree of failure. I’m sad about it, without question, but regret isn’t what I’m feeling. I’d have regretted not trying.

Things don’t always go your way, and in our case it really didn’t go the right way for either of us. I think we’re both bummed about it, and I still walk around with the adoration I had when I sent those flowers…adoration for a girl who’s going to make some lucky guy thank fucking unicorns that he’s got her attention. I still want her perch on the mountain, in front of all the women who look at her for inspiration, wings agape as she drops off the cliff and shows them how to fly.

So I stepped away when it was clear that was my only option.

I stepped away when the guy I’d promised I’d be to her, in order to remain the kind of guy who could actually be that guy to someone tomorrow, needed to be the guy who stepped away today.

How’s your heart, folks?

Soft Lightning Bolts

We grabbed coffee at the first Starbucks we could find, which to many is sacrilegious but in Seattle seems strangely appropriate. Plus she likes Venti iced coffees because Venti means huge, not large.

She walked away from the counter with a breakfast sandwich and scone, I walked away with a scone and order envy.

A minute later as she bit into her sandwich and called me out for wanting one too, I jumped up and got back in line.

This place was unusually homey for a Starbucks, as there was this fall sunlight dropping in through the musty front window, where she was perched on their cushioned bench along the wall, legs crossed, elbows on her lap. She was picking at her scone with one hand and her hair was deep and dark, backlit by orange yellow sunbeams as it fell around her shoulder. She was gazing lazily at the little boy a few feet away who was crawling on his father, a strong man clad in army camos.

She leaned to one side, and from head to toe kind of zigged and zagged in the way only a woman can. In the way that conjours up visions of a slender riverside reed or the rare soft bolt of lightning. The sun behind her froze time.


Just…I mean.

I forgot I was staring.

Her eyes caught mine and bashfully asked “whaaaat?”.

She shifted ever so slightly, almost embarrassed, and smiled as I just shook my head and broke my gaze to turn and blankly stare at the wall behind the counter.

I laughed a bit.

It’s funny how you can’t always remember those moments when she asks you “why do you even like me?“, but in the moment, as they happen, you know that’s why.

If I had to guess, that was a moment she’d never remember about that particular day.

And yet for me, it’s a moment I can’t forget.

How about you…whatchu got that’s unforgettable??

How Are Things Going?

“I’d love to make new friends, but who does that after they’re 30?”

I got that text from a friend I left behind in Chicago, a person I probably miss more than I even realize sometimes. Giving up the world I had in Chicago was a conscious (and consciously painful) decision I needed to make to give dream chasing a real shot.

Sounds all fuzzy and exciting and what everyone should do but that’s when you don’t analyze the real meat and potatoes of what makes life worth living, which is the people you spend it with.

Sometimes you can’t control the way people enter and leave your life, and sometimes they leave in drastic and painful ways, but when you’re wholly responsible for deciding to uproot yourself you carry around that weight a bit, no matter the reason you did it or what the result was.

My situation’s a bit unique, having left home to start a company. I’m in a new city (and country, eh?) and the reality is that lifelong friends are simply not something you can go out and pick up easily. Do people make new friends at 30 years old? Sure. Is it quite a lot harder than at 18, 23, 25?

Fuck yes.

I love what I do every day. I love working on a problem that’s got absolutely no roadmap.

Every single day is a mystery, every accomplishment that much richer because it’s like you’ve birthed it. The conversations you have are almost all based around your little company and ambitions. You learn so much…about yourself and other people and markets and technologies and you look around at the people doing the same thing and you learn from their accomplishments, ideas, and mistakes.

It’s thrilling.

It makes answering the ‘how are things going?‘ question a very difficult one to answer, because until things are decidedly doing so well you’re almost surprised by it all, you’re really just surviving. Things are going well because you get to be inside of your project and the world revolves around your ideas.

Things are also terribly frustrating and scary, because you have no cushion and you have no guarantees and you have no social life and you experience the thrills and rewards of a life you’ve chosen right next to the uncertainties and very real stress of building a company.

People here are amazing, which I think I’ve said, but probably not enough. People like Mac, Maura, Tony, Sonia, Tina, Jodi, Daniel, NoahBoris and Danny (and on and on, really) have literally shaped my experiences here, and have done so in only the way really open, friendly, giving, supportive people can.

You know how sometimes people have their circles and can’t find room for outsiders? These aren’t those people.

These are people full of life and friendship. People full of ideas and ambition and a drive to welcome people into their circles. People who matter because they care about other people.

My kind of people.

So, things are good. And tough. And exciting and invigorating and alive. The heart is still beating and every day’s a new day.

And yeah, I’m still crushing like a fool on this girl. More on that later, I’m sure.

How about you?

How are things going?

Boulder South Bend

When I was in Boulder I was very fortunately pushing Foodtree a step forward and I was very vulnerably seeing about a girl.

A girl who just quoted Nietzsche at me, by the way. Like Oh remember how I know everything there is to know about the Kardashians and throw on cute little dresses that you thought only people in fairy tales could pull off, and I spontaneously burst into song? Oh, I also throw Nietzsche quotes around casually. Also adorable babies think I’m adorable.

I was there, though, at the same time at which a large contingent of my cousins were in South Bend, Indiana, visiting my little sister and attending a Notre Dame football game. Against Stanford.

My family’s rooted in New York, where my parents met, my grandma lives, and I think at least a third of my first cousin’s reside. That’s a third of a pretty big number. Ours is a New England family, despite my having been raised in a suburb in Illinois. In fact, prior to my 26th birthday I would have been less disoriented blindfolded in Manhattan than in Chicago.

Alongside that, New Yorkers are notoriously reluctant travelers, always caught in the flow of the pulsing heart that is New York to the point at which anything less than LA or Europe seems like a waste of a plane ticket.

Nevertheless, my little sister is the youngest of our (massive) generation, and thus has a special place in everyone’s heart, and when one of the numerous ideas for gatherings pops up (most of which are purely speculative at best) involves her it takes on a much more realistic significance.

She’s in grad school, at Notre Dame. It’s cheap to go to Indiana…Katie married a Notre Dame grad who can help us get football tickets > pull out a laptop > flights are booked!

The execution part is usually not our strong suit, as a family, but my little sister is the magic sauce and it happened.

I missed it, and based on my last post I think it’s pretty clear I had a trip I will never forget.  Point in fact it wasn’t a choice, but a coincidence, and I’m grateful I was in the States during the family hang. I could call them easily, trace the Facebook updates and tweets (no data plan in Canada…another conversation), and generally feel closer.

I’m honestly not sure what my point is here. Maybe it’s that I’m intimately tied to the spaces my family makes beautiful. Maybe it’s that I just hope my family knows how much of my heart they fill.

Maybe it’s that I sort of feel like I traveled with my family two weekends ago, and I met someone I like along the way, and I hope you all might understand how great that is for someone who lives so far away from so many people who are important to me.

Where’d you travel last?

Flowers From An Airport

Four lanes of traffic.

Boulder, Colorado is a sexy little town with personality and one of the most crucial comforts of great small cities: a pedway. Room for humans to wander and stand still and shop and contemplate street vendors without the entrapment of a sidewalk and cars. That pedway crosses Broadway, and as she came into view on the other side of the street she just kind of bounced and gave a little wave.

Four lanes seemed like a sea waiting to be crossed.

I sent her flowers a few months back on a whim. I caught wind that her heart had been broken, and I’ve read her blog for years now, so the significance of a shattered heart was as tragic for me as it was for the forty bloggers who began emailing one another hoping to find ways to reach out to her in support. A boy should send her flowers, I thought, and I nearly missed my plane because it seemed so necessary.

The flowers included this note:

I will try to connect with you via back channels, but I just want you to know that you’re one of the most captivating and beautiful women on the internet. You will rock this, and your life is not over. It’s beginning. Much love.

Then here I was, twenty feet from her, standing there in the flesh with her gorgeous smile and deep, deep eyes.

I’m not sure how I felt so comfortable up to that moment…I carried almost no nerves up to Boulder after a day with Chalise in Denver.  I was walking to meet her from one of the most inspiring meetings I’ve ever had, and through my first 36 hours in the area I was massively most excited about meeting her. I was calm; incredibly comfortable that meeting her would be almost easy, because our conversations from afar were like looking in a mirror…

Looking across the street, all my composure disappeared. Took a fucking vacation.

The vision of her was so far beyond radient that I felt unprepared. I felt small, insignificant, and I felt insanely lucky that the light was changing and she was very obviously going to run and jump on me.

I picked her up in a feverish hug in the middle of Broadway.  She popped off to my side, laced her arm under mine, and we almost galloped down the pedway towards the cafe she was eating lunch with her friend at.

I spent last weekend looking at a girl I can’t see past.

Which is to say that I’m very simply happy to feel overwhelmingly in awe of this tender, insightful, sweet person who makes me feel like the person I am today is a better version of the guy I was before. A person fresh off a broken heart and someone who is impressively transparent about her feelings and thoughts and insecurities.

A window-shatteringly beautiful girl.

I think some people in my life and digital circle probably feel a little odd about this particular post. I didn’t give her a lot of context these last few months. Obviously I haven’t written about this, but I even kept a bit quiet with friends and family.

My own sister was a little off on finding out I was in Colorado for more than work. That I was meeting someone I considered significant in the heart department.

That was intentional, wanting to own the experience for myself. I think having been asked about my love life for the last few years carries with it some responsibility; the pool of love and concern around my happiness is deep and I have always thought it important to be sure about my feelings. We’re both internet people, and her story at the moment is especially dressed in her most recent relationship. I have always tried to respect people’s ownership over their own lives, and to write about people who were comfortable with it.

To say she’s alright with me writing about would be somewhat of an understatement:)

So yeah…unicorns and party favors and sparklers and smiles and cake and frosting and whoa.

This girl‘s in my head. Big. Time.

Check her out cuz she’s adorable.