A Hacker by Trade, A Caregiver by Choice: One CEO Finds His Work and Personal Life Are Deeply Intertwined

Caring Conversation — Robby Macdonell

Robby Macdonell is a husband, a caregiver, and the CEO of RescueTime, a time management app that monitors how much time you spend browsing certain websites or using certain programs, and it helps you identify data to ‘reclaim your day.’ A Seattle, WA transplant, he now lives and works in Nashville, TN.

Rajiv: What is your caregiving experience, right now and in the past?

Robby: It started about six years ago. My sister and I were both living in Washington State, and my dad was in Nashville, where he’s lived for several decades. He began having problems getting around, stumbling quite a lot. That time also coincided with a big dip in his depression, which he’d been suffering from for quite some time.

We knew it was getting to a point where dad needed more attention, but we weren’t quite sure what to do about it. Then one day I got a call from my dad that changed everything. He said he didn’t feel like he could be on his own anymore and he needed to move up and live with me or my sister. I lived in a studio apartment, so he moved in with my sister.

His issues are complex. He’s dealing with mental health issues, as well as an ill-defined neurological disorder, sort of like Parkinson’s that doctors still haven’t been able to pin down. Being up in the Northwest went well for a little while, but we all recognized soon that it wasn’t going to work out long term. My dad didn’t like being away from home and decided he was going back to Nashville to try and go it alone. Which, of course, wasn’t going to work.

My wife and I had been considering moving away from Seattle for a while anyway, so we decided that the timing was right to move down to Nashville to be closer to him. I figured that being nearby would be helpful, but probably not too overwhelming because, at that point, my dad was still getting around pretty well. But about three weeks after my dad returned down south, he had a stroke. The situation quickly changed a great deal from ‘How can I help?’ to ‘Wow, I’m in charge of a lot!’ I managed all medications and finances and became his social contact almost exclusively. 

We also had to find my dad a place to live that was safer than his home, so we moved him into a light-assistance senior living facility. That worked well for a few years until he got to a point where he needed more care. Then it was onto an intensive assisted living place where there were plenty of nurses and staff who could take care of the things that had just become too much for me to handle.

It was not an easy on-ramp as I’d originally anticipated — it seemed like every month there was a new challenge that I felt totally lost on. But that’s how it happens, I guess. I’ve learned so much since this all started. Compared to five or six years ago, I realize that the amount I’m capable of handling has grown exponentially. I’ve learned a ton about myself during this process, and aside from seeing my dad through everything, it’s been an eye-opening personal experience.

What is your professional background? Your field of expertise?

I’ve been working in software design and engineering, specifically user experience and user research, for pretty much all of my career. I’m currently the CEO of a company called RescueTime. We make software that helps people be more thoughtful about how they spend their time on the computer. I started out as Head of Product. Around the time I moved to Nashville, our CEO, Joe, a good friend of mine, was diagnosed with cancer. That was difficult for me to come to terms with — me moving to take care of my dad, and Joe suffering as well. He was sick for a few years before he passed away, which is when I moved into his position. I’ve been CEO now for the past 2 years. 

I wanted to be there for Joe as he was experiencing the most difficult thing his life had dealt him, but I’d also just moved away to do that very same thing for my dad. I think when it comes down to it, I did a decent job at being the friend I wanted to be to Joe. But living 2,000 miles away with my own set of challenges definitely made me think a lot about what I could have done if I were closer. Then again, I guess that’s why I moved to Nashville. To be there for my father. It was an intense time. I reflect on it often.

How have your professional skills and perspectives influenced or impacted your caregiving efforts?

Having worked in startups for my whole career, particularly early-stage startups, I’ve gotten pretty used to the idea that if something is wrong in the world, I have the ability to change it. So I went into this caregiving experience thinking that I’d be able to apply some of the same tactics that I use to when I’m trying to find a solution for some technical or business problem. But that’s not possible, really. I think it’s partly because caretaking can be so intense and complicated, that there’s no simple or clever hack that will make it meaningfully better. Ultimately, you know what’s going to happen, so at best you’re really solving problems short-term.

There are so many components to caregiving: technical, emotional, mental. And there are endless logistical links. There’s such a heaviness associated with ensuring the comfort and wellbeing of another human. I was really hoping when I went into all of this that I’d be able to better apply my professional skills, but as it turned out, I had to adjust my expectations. That said, I think my knowledge of user research helped me see things from multiple angles. For example: What does my dad need? Why? How can I make this easier? Better? How are other people in my family thinking about this? What’s the perspective of the woman who comes in to make breakfast every day? That’s all proven helpful. But to be honest, there’s no easy fix. You have to carefully re-calibrate what ‘good’ and ‘effective’ means to you and the person you’re looking after.

It’s the hacker in me that wants to say, ‘Oh, look at this. I can figure it out.’ And in many ways, that’s great. But in caretaking, I almost see it more as a fundamental flaw. In this instance, there isn’t a single solve. And often, it’s the journey to your end goal that shows itself to mean the most.

How has your caregiving experience informed your professional life?

My first reaction to this question is that my caregiving experience has made me rather paranoid in my professional life. I know that sounds unfortunate, but it’s true. Being a CEO is new to me. There are a lot of moving parts that you have to oversee as an executive, and for me, that’s been a big change. But one thing that I catch myself doing a lot is being overly vigilant about things. Like, ‘if I miss some information, it’s all going to go the wrong way.’ And I really think that’s because over the past several years, I’ve become trained from this experience with my dad. And I know that isn’t a positive thing. But after one too many times where I look away for a split second only to look back and find that my dad has fallen, it starts to get burned into your brain.

The positive spin on that is that I’ve gained a new appreciation for consistency and predictability. As RescueTime has grown, I’ve had to rethink how much I can take on, what I can handle. We’ve grown from about 5 people to 15, so it’s a bigger scale than before. I’ve realized that I can’t have my hands in everything. But that’s been very good for me both professionally and personally. At its core, RescueTime is about helping people make sense of their time to do better work. It’s easy to get one dimensional about that, but it’s also important to realize that everyone has different reasons for using the service. People have different demands on both their time and brain space, and therefore they use RescueTime differently. I’ve got a much better handle on the complexity of life now, I think, than I did before. And that’s in large part because of my caregiving experience, for sure.

What one piece of advice would you give someone who found themselves in similar caregiving situations?

One thing I wish I would have done differently is care for myself more — and start sooner! I didn’t listen to myself at all in those early stages. I wish I had started seeing a therapist about a year before I did. Paying attention to those early signs of burnout are so important, both for you and the person you’re taking care of. There’s no need in being overly prideful, as it adversely affects both the caregiver and the person being taken care of.

Communication is also key. I know for my wife and I, we both made a lot of sacrifices for my dad and for the situation. But it all happened fast and we didn’t exactly recognize just how much stress it would put on both of us. We made it a point to create a little ritual for ourselves that every Sunday, we go to brunch or coffee and just spend time talking about our week and what’s on our minds. When you have so much going on with your caretaking reality, professional life, and whatever else, it’s easy to sometimes let those other important relationships atrophy. It takes work not to. And of course, carving out this type of time may not work for everyone, but I think just acknowledging and recognizing that communication needs to come up in some very honest and transparent form is key. It really has been for us.

I also think adjusting your expectations for what’s happening and what’s happened is important. Recognizing that not everything is going to go directly to plan, and that that’s okay. Taking time and understanding to actively re-calibrate and get comfortable with that understanding that being a perfectionist doesn’t do anyone any good.

Interviewed: 11 October 2018, by Rajiv Mehta; edited by Julia Rubano

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