Day in the Life

‘It’s about keeping your feet on the ground:’ A day in the life of Kristen Anderson, the CEO and co-founder of Catch

  • As CEO of Catch, an up-and-coming payroll and benefits platform, Kristen’s days tend to be pretty chaotic.
  • But it’s the little things – like brushing her teeth – that keep her centered.
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‘It’s about keeping your feet on the ground:’ A day in the life of Kristen Anderson, the CEO and co-founder of Catch

As people’s work days continue to take up new forms, the freelancer market remains a hotbed of opportunities for fintechs hoping to service the segment. 

Catch is one such company. Catch’s app offers its users a way to automatically put aside money for different savings goals, including vacation days and retirement funds. It also helps them find benefits they may otherwise have a hard time getting without an employer.

“Our users tend to have complex income stories, and need an ability to automate their taxes, get their retirement in order, and most importantly, access that high quality health insurance that so many of us depend on here,” said Anderson.

In addition to being a super young company, Catch is treading on new ground by being the first of its kind to focus so heavily on freelancer benefits.

That means there are a whole lot of tasks on Anderson’s to-dos, and a whole lot of unknowns on her mind.

But she’s found a way to deal with these things – by not belittling the routine parts of her day, and keeping a one-coffee-a-day mindset.

Here’s a day in her life:

Mornings: spending time with the little one, making coffee, getting going 

I have a 10-month-old daughter, who is a delight and a wonderful part of my life. She’s also my alarm, for sure.

So my morning starts with spending time with her and making sure that she’s ready for her day. 

My partner and I have a really nice little routine where we get our daughter up and give her her bottle in bed with us. It’s very sweet. 

And then we prepare her for daycare. My partner and I have a pretty steady handoff between getting everything done. We try to get to the office between 8:30 and 9:00. 

I guess there’s nothing particularly fascinating about my mornings, but it’s a really special time to spend with my daughter, since she’s in daycare for most of the day.

I would like to say I’m actually not addicted to coffee, but I do have a pretty nice coffee ritual every morning. Turning on the Nespresso machine, hearing that little buzz, and knowing the coffee is coming is a really important part of the day for me. 

In general, I’d say I have an inclination to moderate in my life – to stay in the range of what feels centered and normal.

So I’ll have one cup of coffee and never have two, let’s say. And that Nespresso routine is really important for me.

I also find brushing my teeth pretty ritualistic: I use an electric toothbrush, and I think there’s something to the timing of it that feels very organized and diligent – especially since sometimes a baby can throw everything into chaos. 

And you’re just like, ‘Okay, now I get my two minutes to brush my teeth.’

I think because work is so intense, and company building and growing and hiring and fundraising and all of those sorts of things are extreme, I like to keep what I can low-key. 

So the parts of my personal life that surround my day are usually mundane – that might be the best way to put it: Simple meals, regular exercise, going to bed at a fairly consistent time as much as possible, maybe even a nice glass of wine – all of those sorts of things are what really help keep me centered.

I’d say it’s about keeping your feet on the ground, when all sorts of wind can blow in different ways on any given day at the office.

Diving into the workday: filling buckets with boulders 

A CEO’s job can vary a lot day to day. I think on any given day there are large buckets of things that are always on my mind. 

One is our customers. That bucket can manifest in different ways. Generally, though, it is about understanding who our customers are, what they need, and how we can best support them.

That’s probably my favorite bucket. Our customers are fascinating. They cover all sorts of professions – everything from an in-home chef, to a hairstylist, to a tattoo artist. Our customers are truly interesting people, filled with unique stories and various passions.

The second bucket has to do with hiring. That’s where we need to figure out what people are needed next, how we’re thinking about the future, and how leadership in the company is being rolled out. These are the really big questions that affect our trajectory probably more than anything else.

I like to think that I have a lot of control of where this company goes. But the only thing I really can control is who we hire. Our team is really what moves everything forward day to day. 

As for how I like to organize my time, it really depends. 

I have heard some really interesting tips from other founders and CEOs on their methods. I think the one that’s worked best for me is keeping a monthly view of things, rather than a daily one. 

That means asking myself what it is I want to accomplish this month, understanding how important those things are, and then tying them back down to the day-to-day tasks. 

Sometimes you don’t have control over these things – but you can still figure out your targets and plan according to that. 

Right now, growth feels like the biggest thing that we need to put effort into. That means that I need to make sure on any given day, 30% to 40% of my time is spent on growth. If I’m spending five or six hours a day on legal or operations or some of those other things, then maybe I’m not doing my part to make sure that those big milestones are hit. 

There’s a framework called ‘boulder, rocks, and sand’. This framework gives you an idea of how to think about the massive chunks of your work, and then how to think about the smaller pieces in-between, enabling you to think about ‘fillers’. I think this framework helps us make sure that we’re speaking enough time on the boulders so that our time isn’t lost in the sand.

I think that framework sort of helps us make sure that we’re spending enough time on the boulders so that our buckets don’t end up full of sand.

Evenings and winding down: Un-working and re-working

When I was younger – you know, pre-baby – my workday would go until about seven o’clock, and then I would go home and shut off. 

That’s a lot harder to do when you have a small child at home. And I remember hearing from colleagues who had children and thinking, wow, it must be such a bummer for them that they have to spend this window around dinnertime with their kids, and then have to pick up work again after that. 

But now that I have a child, I actually find that I really, really love that. So I’m basically offline from 5:30 to 7:30. That’s when I go pick up the baby from daycare, and we have our nightly routine – you know, a bath and dinner and all that sort of stuff. 

She’s generally asleep by 7:20 on the dot. 

And then I pick back up again at 7:30. 

The mental break I get from this time helps me turn off my work brain completely for a couple hours. And I find it lets my thoughts process and marinade.

I even sometimes find that when I come back online I’ve solved a lot of work problems subconsciously.

And I think that’s been a really effective way for me to work in the last year or so since the baby was born. 

I really appreciate that time, because, especially as a CEO, that 7:30 to 10:00 window is usually quieter.

There are fewer people who need things from me during those hours, which means that I can chunk out things during the day because I know I have that two-hour window at night to crank through this work and get it done before I go to bed. 

It means that I can go to sleep feeling fairly accomplished because I don’t have that last bit of work hanging over me. 

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