Hi, I’m Benjamin Chait. After backpacking around the world, I spent six years in PDX before moving to SF. Say hello @benjaminchait (or email) and let’s grab coffee?


It’s never too late to start over.

It’s never too late to make the move.

It’s never too late to explore a new place.

It’s never too late to try building a better thing.

It’s never too late to start something new.

It’s never too late.

Six years west

Every morning I wake up and look outside my bedroom window at a view that still amazes me.

The days are long. This city is, for lack of a better word, hard. (Maybe all cities are hard? But in different ways.) My days start before dawn, taking Lyra for a walk around the neighborhood before the city is fully awake. We make it back to the apartment as the sun starts to burn off the fog; the pup is fed; and I head off to work. Work is work. Just as soon as I walk back in the front door, I turn around and take Lyra out for another jaunt. It’s dark early, being winter, so I’m usually wrapping up and starting dinner with the glow of the city’s lights outside.

It’s all a lot, but we’re settling in. The first couple of weeks were staying in a temporary spot; and the pup and I moved into our own spot in November. We’re living in (or perhaps it’s on?) Russian Hill. The first week had me sleeping on a couch; then I got a bed, but didn’t have anything for the kitchen. Last week was adding some lamps; next week I want to sort a bookshelf. And I’m grateful that Lyra is adjusting, and seems to be falling into a routine in our new urban spot. It’s a process. But it’s what I wanted.

I won’t lie: I’ve wondered more than once, why did I move here? I love the Pacific Northwest, and miss it. The wide open spaces, the pace of life, the lack of sales tax…and yet, SF gives me new opportunities, mostly important the opportunity to start over. And it’s still the west coast.

I’m a bit silly, and continuing to work in consumer financial tech – but this time, I’m in at the beginning, building something from nothing. It’s a risk, it’s a startup. If anything, I’m choosing what will give me the best opportunities to learn, and to grow. This is my chance to start from the beginning, in more ways than one.

I can’t say that SF is forever, but this is perfect for now.


Standing here, looking at an empty house which I no longer own. Most everything I own in boxes, much of it packed away in the recently-repaired car. Lyra pup following me everywhere, so sweet yet a bit uncertain as to what all is going on.

This is my last night calling Portland home.

I have so many memories from my time in this city. I remember the first few weeks, trying to get settled in a new place. Finding a job. Building a group of friends (it’s surprisingly difficult as an adult in a new city). I remember exploring new neighborhoods, finding new places to enjoy on evenings out or spots to meet up with folks after work. I remember finding our first apartment, and moving to our second. I have so many joyful moments, from celebrating accomplishments with those around me; to bringing home a pup; to buying a first house; to bringing home Lyra. Some of those memories are really, really great. Others, not so much. I’m still heartbroken.

Almost six years ago, I moved here. (Well, we did, together.) But, life doesn’t always work out in the ways you plan. Tomorrow, the pup and I hit the road to start our next adventure in San Francisco.

The Pacific Northwest is a special place. I am so grateful for all those people who came into my life. With whom I worked. With whom I could have hard conversations about life, love, and jobs. I am so so grateful for everything.



I’m happy.

This past year hasn’t been easy, nor what I expected. But at the end of the day, I’m living my life. And I’m okay with that.

I’ve spent a lot of time trying to figure out me. What do I want to be when I grow up, who do I want to be? I’ve been fortunate to have had a number of opportunities and decisions, and through all of that have made choices that kept me here. In Portland. I decided that I’d rather be running toward something new and exciting, than running away from something in my past. And in committing myself to where I am, to this place, I’ve also realized that I’ve been asking the wrong questions.

(It’s funny how many of the best lessons occur both at work and in my not-work life at the same time.)

Who am I to think that I’ll know what I want to be, some number of years from now? I thought I had to have a plan for my future, for what I’d be doing, for who I wanted to be. But instead, I’m focused on the here and now. I’m open to my future being unknown. If anything, I’m taking each day as it comes.

Instead, I’m trying to answer: What are those rituals and routines I want in my life?

My hope is that I’m growing and getting a little bit better, each day. I’m trying to eat healthy foods, and to take care of my own self. I have a bedtime, and a morning ritual to take Lyra out for a walk around the neighborhood. Don’t get me wrong, I’m not perfect. But I know what I’m striving to achieve each day.

Do right by those around me.

Do good work, at scale.

Make time for myself, and my family. Disconnect, take a walk with the pup and explore.

Look forward, never back.

Five years west

This year wasn’t what I expected.

The first part of this year was rebuilding. Lyra joined the family, the basement was fixed.

The second part of this year was personal. Tough conversations, and decisions which still feel raw.

The last part of the year has been sorting: what next?

I’m exhausted. But I’m optimistic, and looking toward the future.


I’m not sure where to begin with this past year. This past year has been a blur, including some of the highest highs and the lowest lows. This time one year ago, I felt everything was falling together just right; a few weeks later, and everything was falling apart.

The time since has been spent rebuilding.

Homeownership hasn’t been easy. It’s been pretty terrible, to be honest. From the very first rain of the season, we had standing water in our “finished” basement. It was only a few days until we removed the carpet, and portions of the drywall. We dealt with insurance; we argued with the seller; we spent hours with contractors, evaluating repair options. We got estimates, we signed bids, and then we waited. Months passed, and we tore the basement down to the foundation, waterproofed it, and began the long process of re-finishing. We’re almost there.

In February, Sarah and I brought home an eight-week-old pup we named Lyra. Neither of us were planning to raise a puppy this year; regardless of when, it’s a lot of work. Lyra joined us from Colorado, and though she’s a half-sister to Kippa, she is entirely her own, unique personality. She’s fearless, and fiercely loyal – the first night we had her home, she escaped from her ex-pen in an effort to be closer to her people. It’s different, this second time around. I’m not an expert on raising a dog, nor am I really all that better at training and caring for a small being. But I’m so incredibly grateful for the joy and excitement this little one brings to our home.

I could never have expected what this past year would bring. I’ll be honest: A lot of the time, I think I’d be happier if everything had been different. But I’m not going to try fighting what I can’t change.

I’m learning what matters, to me. I want to make a positive impact. I want to take something and leave it better than when I found it. My time is valuable, and limited: I’d rather spend it solving real problems, and helping make the world a slightly better place. I’m looking to grow, and to keep building skills and experiences.

At the same time, I’m learning how to take care of myself. Some evenings I just have to close my laptop and call it a day. I’m pushing myself to disconnect more often, or to be more deliberate about my use of technology on weekends and during evenings. My daily evening routine includes taking a long walk with Lyra, to get outside and to spend a few minutes in my neighborhood. This month, I gave up my parking pass to force myself to cycle again.

I’m learning how focus my energy, and how to spend my time on me. I’m learning when to say no.

After a year of challenges, and unexpected lessons, I’m focused on the future.

Four years west

This year started so incredible: my work was going well, Sarah began her Physician Assistant program in the summer and we purchased our first house. Everything was feeling really, really good.

Then, all of a sudden, it fell apart.

This fall was full of stress, loss and heartbreak. Work intensified. The finished basement of our house flooded, and is in disarray while we plan repairs. And we lost Kip.


You know, I never considered myself a dog person. Growing up, my family never had a furry friend, mostly because we’d be skiing or traveling or generally didn’t want the added responsibility. (Also, I’m betting some part of it was not wanting to clean up and maintain a house with a pet.) I had a cat after college, who found a new home when Sarah and I left the country. Once Sarah and I settled in Portland, her cat Taches joined us. But for years, Sarah had slowly, repeatedly suggested that we might one day have a pup.

The week before we brought Kippa home, I’m not sure who was more terrified: me, not knowing what we were about to get into, or Sarah, who was worried I wouldn’t be happy with a dog in our home.

I couldn’t have loved Kippa more. She was the best, and taught me the joy in small moments, every single day. She loved, unconditionally. She was a goof who always had fun. I miss that silly, floofy pup with her wet nose, floppy ears and fluffy tail snuggling up just to be…close. She’d sit between my legs, flip her head backwards with her tongue hanging out, and would be full of love.


I don’t know what to say. I thought 2016 was rough, and I never imagined 2017 would be so much more challenging. I’m grateful for my family and friends, and the love and support I have from Sarah. I’m cautiously optimistic as I look toward the next year.


We lost Kippa last week.

A few weeks ago, we were so excited to receive the keys to our first house; we’d spent the past few months looking, and found a perfect little house with a beautiful fenced yard for Kippa. We slept on the basement floor in sleeping bags that first night; Kip was so happy to have her “pack” sleeping with her that she kept waking up every few of hours, checking to make sure we were all still there and then snuggling beside someone else. Kippa absolutely LOVED her backyard, and spent hours rolling around in the grass and sniffing, playing and digging.

But a few days after we had finished moving, she got sick. We took her to the vet multiple times, and ultimately the ER. She was in surgery for multiple hours when we had to make the choice to say goodbye.

We’re heartbroken. Kippa delighted so many people during her life; she was loved so very much by all, and she herself gave so much love. She was our joy, and we were so so lucky to have her.

I wish we had had more time.



Today is thirty.

As I take a moment to think about where I am, and what amazing opportunities and experiences I have had thus far, I am humbled and thankful. Eager and excited. So incredibly fortunate to have an amazing partner, a loving pup and to be surrounded by incredibly people both at work and beyond. To have built a community here in Portland. 

I’m often reminded about how much I have grown, and myself changed. When I was eighteen and headed to university, I—like any recent high-school graduate—thought I knew everything: what I wanted to be when I grew up, what I was going to study and who I wanted to be. It only took a few short weeks of my freshman year before I realized how wrong I was; rather, how much I had to learn.

Fast forward to graduating college: I was fortunate to work in a job I loved, splitting time between Colorado and California. At that point, I realized how much I had changed in only a few short years, and began to recognize where I was spending my time and energy. I wasn’t working in politics; in many ways, I wasn’t as involved as I wanted to be. And then I found a great opportunity; being at the right place at the right time gave me a chance to participate, and to build a new set of friendships which I still have today. This was great, for a while, but I soon began to feel restless.

Eventually, I took a leap of faith and invested my time, money and energy in travel, and in myself. It was challenging, amazing, eye-opening. It wasn’t what I expected; then again, what transformative experience actually is? I started to pay attention to my heart.

And now comes my time in Portland. Our time in Portland. Sarah and I been here three-and-a-half years, and I love this place. The people, the coffee, the outdoors. And I begin to realize: I am who I a today, because of everyone, everything around me. And I realize, without a doubt, I am not the same person I was when I first arrived here. I’m learning empathy, and how to slow down. I’m learning the simple joy of coming home, to a pup who is adoring and excited and happy. A kitten who keeps to herself by day, but sneaks up to lie beside (or on top of) me every evening. I have a loving partner, who is incredible and drives me to be my best self.

And I think about who I want to be, should I one day grow up, and I realize: I am exactly where I want to be, and who I want to be.

Thirty on the thirtieth.

Three years west

The sun came out after a rainy morning, one last warm glow in 2016. Not quite cold, though not quite the warm California weather we were expecting. Rather, hoping. 

Looking outward, the past year has been rough. But personally, 2016 was good. Kippa joined our family, Sarah was admitted into (and accepted) a graduate program and we continued to explore and enjoy the Pacific Northwest. We’ve made new friends, and become more active in our community. 

I also accomplished two small, silly goals I set for myself one year ago: practice French and post a photo every day. (Being a leap year, I succeeded in both of these 366 times.) By no means am I fluent, nor a professional photographer; instead, I’m feeling more confident, and making practice a part of my routine. Small habits are hard to build, but I’m excited to have proven I can. 

I’m not quite sure what 2017 will look like. I’m more anxious today than I was this time last year. But I’m also fortunate to have friends and family with me in this journey.