Growing From Multiple Hardships at Once, With Maddie Burton

Maybe it’s not typical for an interviewer to be so biased about their guests — but I love

Maddie Burton

. Maddie is the author of “On The Cusp,” a newsletter with thousands of subscribers that she began last year, after experiencing a series of difficult losses. Despite being a self-described “overplanner” — who was a financial planner for a living — her plans went “up in flames” when she finalized a divorce, lost her mother to cancer, and got laid off from work, all within a few months. Her story immediately resonated with me, as someone who went through several life transitions myself recently. 

Today, Maddie is the self-employed owner of a web design studio, and has reshaped her newsletter from “Your Five Year Plan” (about life going up in flames) to its current evolution, “On The Cusp,” about embracing the new and unknown. Her writing is thoughtful, meditative, and beautiful, and full of practical tips as much as profound, larger explorations. 

I hope my presentation of the conversation allows you to experience the same peace and serenity I felt speaking with her. 

Let’s start at the beginning. What was your life like before these big transitions that you went through? What kind of person were you? 

What’s interesting is, really it's been many years since I wasn't going through transitions of some kind. I lived in Chicago for a number of years before I decided to move out west to the Seattle area. I got engaged, planned a wedding, got married, bought a house. 

But I will say the positive and run-of-the-mill changes —moving, changing careers, getting married —somehow those experiences didn't shift the way I thought about life in the way that the really negative ones have. Even though the positive changes were just as destabilizing. 

I’d say before I was also much more achievement oriented, white-knuckling my way through life. More attached to some kind of certainty.

When you began facing these difficult experiences, what were your reactions? What were the thoughts going through your head? 

The divorce happened first, and I felt shame. Because I was, you know, “only” married for three years before we separated. I was in my mid-thirties when that happened. I didn't know of anyone my age who was getting divorced. 

There was shame around the length of my marriage, but also this overwhelming question of what more could I have done? Like, I tried so hard. Shouldn't that mean that it would be a success? This idea of tying my effort to the results? 

When my mom told my brother and I that her cancer had returned, that was really scary.

At that point, she was still going through the machinations of, which treatment path do I take? But within a couple of months, it became clear that the treatment that she chose wasn't working, and she went into hospice. It was overwhelming both emotionally and logistically. First, there was the emotional challenge of losing the person that I relied on the most, loved the most, and who I had assumed would be around for another couple of decades. 

Changing that, just that frame of reference, on how much time I had with her…caused whiplash. The other part of it was logistically not understanding how to be a caregiver for somebody. 

I'm lucky that I had a huge support system, so I was never alone, but it wasn't a role I was prepared for, especially with my mom choosing home hospice care.

As for getting laid off, in some ways, it felt like, of course this is happening. Like, this was the last thing that could go wrong, and so, of course, it did, right? (laughs)

Honestly, yeah. Like, what else could go wrong at this point? 

I just remember it was three weeks after my mom died. It was the day that movers were coming to move everything out of her house. And it happened that day, while I was technically off, taking care of this horrible, monumentally challenging task. So, yeah, it felt even more ridiculous, because of what else was happening.

You started your newsletter two months after these events. What was it like sharing your journey in public? 

It was emotionally vulnerable, but in some ways, it was useful that everything in my life had blown up because I really, genuinely felt like I had nothing left to lose. And I say that in a positive way. I felt like I could share because — what was the worst that could happen? Someone would roll their eyes at me? Like, I've dealt with worse at this point. So in some ways, it was freeing. 

Well, that’s interesting, because I always feel scared to share anything. 

Have you ever heard the phrase about change only happening when the pain of change is less than the pain of staying the same?

Yes. I work in sales, so we say that all the time (I laugh). 

Yeah, it's a cliche, but the pain of not having someplace to process these things was worse than any embarrassment that would have come from sharing them. Early on it was also helpful that I had some cheerleaders in my close friends. And when I shared my first piece, I had a few acquaintances reach out and say that they were so glad someone was writing about this because they also had an aging parent and were grappling with what it meant to be a caretaker for them. 

I knew I was on the right track when sharing these stories publicly was helping me make genuine connections with people who, previously, were more like “professional acquaintances” to me. 

In your work, you do emphasize the importance of connection, and interdependence. 

Being with my mom through her hospice care at home, and helping to pick up the pieces after she died….that really did stress the importance of connection.  I think we talk about “connection” a lot, but I don't think I truly understood what it was to be connected both to her, and also to all of the people in my community, and her community, that helped both of us through that experience —until it was happening. 

Actually, to your previous question, about how I was before —I probably moved through life a bit numb, at arm's length from even the people I cared most about in my life. And not even realizing that I was doing it.

There might be some people who, in order to deal with the pain of any kind of loss, numb themselves out. But my mom was just, you know, such an important part of my life, and as she went through hospice, it was so clear that I had a very limited amount of time with her left, and I couldn't afford to be numb. It was impossible to. I had to be present with her through that, as hard as it was. And I think that taught me a lot about connection.

What has it been like watching your subscriber base grow in public? 

I think I've done a good job checking in with myself, and that anything I'm sharing is first and foremost coming from me, and not from external pressures. 

I've done my best to kind of manufacture blinders for myself. When you have email subscribers and charts and graphs, it’s really easy to start responding to what other people want from you, what you think they might want. In some ways, I miss the days back when I had a food and travel blog, when I didn’t know who was reading it. It was probably only my mom, though. 

In one of your posts, you had a quote from

Bruce Feiler

that stunned me: “the essence of chaos is self-organizing.” That completely reframed the way I thought about life upheavals — that instead of being disasters, that they’re important agents for change. With that quote, for me, it’s hard not to see difficult experiences as spiritual. How do you see them, though?

Ooh, I think that quote came from a piece I did on creativity and uncertainty (linked here). I think if I have any kind of spiritual practice — it’s probably my creative practices. 

I started to really, viscerally understand that creativity —which had always been a part of my life — I had always loved writing and photography — that it actually benefited from uncertainty and chaos. That you could not only find beauty, like finding the silver lining in a thundercloud, but that actually, creativity doesn't benefit from sameness and order and rigidity. The more I began to understand that, the more excited I got about chaos. And chaos maybe isn't the right word, but certainly uncertainty, which was never a place that I liked to live before. 

So that leads me to ask, what are the thoughts going through your head now that you've emerged from this period of a lot of difficulty? 

I'm so glad that I've had the past year to process everything that happens, and it's such a huge privilege to have been able to have that time. But it's not a space that I'm going to live in forever. I'm going to carry memories of my mom with me forever, and I'll continue to write about her and she will continue to impact how I view the world and how I make decisions moving forward. I'll continue to look back on the lessons of my former marriage as I move forward into a new partnership. I'll continue to look backward at lessons from the career path that didn't quite work out as I work towards a new vision for my career. 

But I'm not going to live in the past. I feel better equipped to follow my curiosity and step into what's next. 

I can definitely see that in your rebranding from “Your Five-Year-Plan” to “On The Cusp.” You’re stepping into something new.  Now that you are in this place, though, do you ever get afraid of another series of — I don’t want to say disasters, but huge difficulties coming your way? 

Of course. There are ways in which I am self-protective or maybe just more thoughtful, more cautious. 

But I do feel confident now that there are a lot more things that I can get through than I did before. It would make sense that coming out of all of this loss, someone might approach the future with trepidation or fear. But it’s the opposite for me.

The scarier thing to me now is not living fully and running out of time. That is almost certainly informed by my mom's passing at 68, as she was beginning her retirement. She worked so hard for so many years to get to the place that she was in, and she didn't get to enjoy it. 

I think she was mostly at peace with it. But as someone who used to live for the future, whose organizing principle was taking care of my future self, and making my present self endure a lot of challenges for the sake of tomorrow, I do a much better job chasing down things that I want to do, and prioritizing them in the here and now. 

What would you tell someone who is going through a series of really difficult experiences?

I did a lot of work, both for myself and hopefully for the benefit of other people, thinking about the commonalities of the losses that I went through. And it dawned on me that the commonality was uncertainty. 

I tried to distill that into a framework that hopefully people find useful (linked here): it’s four strategies. It’s leaning into self advocacy — the idea that as hard as things are, you have agency. Leaning into interdependence, instead of trying to muddle through things alone. Then, adapting your mindset  and having a creative outlet. Among the four, I think when things are hardest, leaning on your community, that interdependence, is most important. All these things I’ve written about at length, but it was important for me to distill this exhausting, mind-bending experience into something useful.

Speak of interdependence — thanks to fellow Substack writer and friend Chris Anselmo for introducing me to Maddie. Want to subscribe to Maddie’s newsletter, On The Cusp? Click here.

What are your experiences with experiencing loss? Several difficult experiences at once? I’d love to hear your thoughts below.