For this episode of Finding My User Manual, I sat down with Joanna Montgomery, a founder and CEO who builds technology for parts of life where people aren’t rational, including love, grief, intimacy, anxiety, connection and care.

She’s best known for creating Pillow Talk, a connected product that allows people to send their heartbeat to someone they love. Used in over 80 countries worldwide, it has supported couples, families, hospitals and individuals navigating distance, illness and loss, turning technology into something deeply human and emotionally resonant.

I had the privilege of meeting Joanna towards the beginning of last year, and we immediately bonded over a deep love of authentic conversation. So when I was planning who to have in the first few episodes of this podcast, it was obvious she had to be one of them.

What struck me most about our conversation was how Joanna Montgomery approaches life with such fierce authenticity, backing herself even when it means closing doors.

Here’s what she shared.

Our User Manuals Must Be Vast Dossiers

When asked what would be on page one of her user manual, Joanna thought about it all weekend. The more she thought about it, the more she realised our user manuals are huge. “The front page should probably be a contents page”, she says.

If you just met someone and needed their manual, you’d look for the relevant bit. “Where’s the friendship section? Chapter three.”

“Our user manuals must be vast, vast dossiers.” To Joanna, thinking that what’s most important is on the first page is probably naive, and thinking that we can be condensed down into something small enough that the first page will hold enough meaningful information is not plausible.

Building Technology For Irrational Humans

Joanna’s business came about by accident. It started as her university project and ended up going viral on the internet, and she never set out to run a business.

She studied interaction design, which is fundamentally how we interact with technology. Over the four years she was at university, things shifted so fast. As soon as the smartphone came along, everything became about that device. It set the user manual for all designs, all technology, all products; but screens are so unnatural to us as humans.

Joanna Montgomery had a moment where she looked around the studio at what everybody was building, and it was all about a screen or an app. Something two-dimensional that either interrupts us constantly with notifications or forces us to schedule time to connect to somebody. She thought “this is very misaligned with how we actually interact as humans”.

That was where the idea for Pillow Talk came from. Rather than building technology and adapting humans around it, how can we build technology that is adapted around how we already operate? How humans have developed, connected, bonded and formed communities for hundreds of years.

We Just Want To Feel Connected

“I sort of realised when you’re away from someone, we either get interrupted by our devices, the notifications, the phone calls, the texts, or we have to schedule in time to sit down.” Joanna was Skyping someone one night and thought it was so bizarre – “this is the equivalent of coming home from work and sitting with a partner and saying, ‘shall we sit down at five o’clock and have a conversation?’ You just wouldn’t.”

The starting point was thinking, “how can I use technology to let us sit in the same room as somebody else and feel a sense of their presence?”

The heartbeat is so deeply personal, and everybody’s is unique. “There’s something about that connection that it has only come from that person you love, whether it’s a partner, a child, or a dying parent. It is them. It is the essence of them and their life force and their aliveness being sent to you.”

“We think we want gadgets, notifications, and FaceTime; we think they are adding to our connection with another person. Until you’re put in a painful, scary, vulnerable, terrifying situation, maybe you have a child in the hospital, or you’re on the other side of the world from your partner. It’s when you’re in that situation that all the noise falls away and you realise, actually, the only thing you really want is to feel connected to that person.”

Connection To Place And Moment

I asked Joanna about times she’s felt most connected in life. One of the first things she thought of was a connection to a place.

One of the first times she went to San Francisco, she landed at night, went to where she was staying, got up the next morning, and was in a taxi. They came up over the hill and she could see it all in front of her, the sea, and she had this full-body exhale. She was starting a new chapter, and it was so exciting for her. It was less a connection to the place and more a connection to herself, her growth, who she was becoming. She still always thinks about that moment and how profound it was, how she felt it in her whole body when she came over that horizon.

We’re Not Trees

Joanna Montgomery is a very transient person. She doesn’t really feel connected to any core place or have a place that feels like home. She lands where she lands. She’s lived all around the world and travelled a lot, and sometimes she likes a place, sometimes she doesn’t, but when she moves on to another place, she just doesn’t miss the other one.

“Home is really just where my heart and my feelings are at that time, and it could be anywhere in the world.”

Fleeting Connections

Years ago, Joanna was on a train from London to Newcastle. There was somebody across the aisle who was acting unusually. He had a notebook out and was writing the same dark sentence out over and over again, so she decided to talk to him. They chatted about various topics, such as the fact that he’d lost his job. When they got off the train, he said he really appreciated the conversation, that he’d reflected on what they said, and actually, he was going home to do things differently.

It would have been really easy for her to look the other way, but that one conversation, by his own admission, had completely changed the trajectory of where he was going.

A lot of people do that for us, even in really small ways. You just never know what your good mood or whatever energy you’re putting out into the world is going to do for someone else that day.

Young Jo

Young Jo was probably “pretty stubborn, and always pretty determined”. She was going to do what she was going to do, and was probably always quite driven, and always felt like she had something to prove.

Where does that come from? Joanna thinks a lot of who we are comes from our parents and how they encouraged us. She was always fairly encouraged, but always also probed to see, “could that be better?”

She was book smart. As far as her school and teachers were concerned, she was clever. She was in the top set and because of that, the system layers expectations on you. She was told she should be a doctor because that’s what smart people do, but she’s way too squeamish. So instead, she should become a lawyer, and apply to Oxford or Cambridge. Which also wasn’t aligned.

“A big part of being an overachiever sometimes comes from being good in the first place, and then everybody else layers their expectations on you, which makes you foster a feeling of self-pressure to constantly be more, better, faster, smarter.”

You’re Like A Balloon

Near the end of university, her project had gone viral, and she was bouncing around the idea of making it into a business. She had a meeting with someone at her university, bounced in energetically with her business plan, and was met with and exasperated “Oh for goodness sake Jo, you’re like a balloon, and you need to be just tied down so that you can’t float away.”

She remembers the crushing feeling. “Am I a problem? Am I too much? Am I trying to fly too high?” That was the first time anyone had articulated that feeling she’d sometimes felt from other adults throughout her life. That she was meant to stay contained where people expect her.

Somewhere along the line, Joanna stopped complying. She never felt like she didn’t fit in or didn’t belong, but she always had this feeling that she wasn’t meant to be in the lane everyone was trying to funnel her into. “I think as I got older not just as a as a child and a teenager but as an adult I just came became a bit more confident in that”.

Self-Advocacy

When asked, “What do you do now when you meet people like that?” Joanna thinks you just have to have a level of self-trust. She can advocate for herself in a way where even if she knows this person’s not going to like this, it’s going to close the door, it might blow an opportunity, she’s learned the hard way that she doesn’t want to work with people like that.

“We owe it to our previous selves to advocate for ourselves and stand in our own power. And we owe it to the people in the room who haven’t yet found that power, that voice, the courage to stand up for themselves. You can’t be what you can’t see.”

A Season Of Surrender

Right now, Joanna is in a season of going with the flow. She’s had some quite intense periods of work recently, and she’s trying to be a little bit more present, more expansive in a way that doesn’t feel like pushing, more like it’s unfolding.

It feels quite strange. For her, as a very disciplined person who used to be a competitive weightlifter, surrender is challenging. She knows she has to train a certain number of days a week, even if she’s tired, even if she doesn’t want to. To some degree, that discipline is part of her identity. She’s a person who does the hard things even when she doesn’t want to, because “it’s a vote towards her future self”.

The challenge in a period of surrender is finding the line between honouring yourself versus making excuses. Is her body actually telling her to rest, or is it just not convenient? That’s what she finds tricky about these periods.

The Box Under The Bed

The fun thing about a surrender period is there’s lots of time and space for impromptu hobbies or side projects. What has Joanna picked up? Falconry and woodturning.

She has a literal and metaphorical box under her bed of side projects, business ideas, prototypes of things she’s started to make and then not finished. “The nice thing about being in a sort of surrender period is there’s just lots of time to revisit those things.”

Self-Trust Over Self-Acceptance

For anyone on a similar journey, Joanna’s advice is this: “The pursuit of self-acceptance is not always the right thing. The more useful thing for a phase of life like this is self-trust.”

“Being able to trust yourself enough to move through it. Leaning into that intuition about whether something is right for you. When an opportunity lands on your desk, do you feel you’re expanding towards it or shrinking away from it? Do you feel a sense of obligation? Do you think you should do it because it would help someone out or because someone else might think more fondly of you? Just really sitting with: is this actually right for me now and for the person I want to become?”

One of the best pieces of advice she’s ever been given is: ” What would the version of yourself that you’re trying to become do?”

“Money is a big one. People have a dream, a goal, something they want to do. They want to start a business, and they get offered a job, a pay rise, or another contract. They know they don’t want to do it, but they’re letting the fear of what if this thing doesn’t work out pull them towards it.”

“Having the self-trust to back yourself and to move towards something hoping it will work out is one of the most helpful things you can try and cultivate for yourself.”

Listen to the full episode:

Connect with Joanna Montgomery

Website:

joannamontgomery.com

littleriot.com

Instagram: @joannamont and @littleriothq

Youtube: @JoannaMontgomery