Reflections on Facing Multiple Setbacks at Once

I had chills while editing, rereading, revising the conversation I had last time with Maddie Burton, author of the newsletter “On The Cusp” (original interview linked here). Maddie began her newsletter last year, after facing a series of difficult losses in quick succession: the end of her marriage, the loss of her mother to cancer, and getting laid off.

As someone who is a fan of Maddie on a personal level (I’m so proud to call her a Substack friend and ally!), I knew I would enjoy the interview, no matter what we ended up talking about. But what I didn’t know was how much her words would ring true to me, and shake my core. Something in me shifted after speaking with her. It’s likely because her insights are so sharp, so well-thought out — you can tell that she’s a writer who’s deeply clarified her thoughts on these topics (more on that below).

If you didn’t have a chance to check out the original conversation, you can read it here.

Check out 6 insights from my conversation with Maddie— and how they relate to the other stories of setbacks we’ve seen in the newsletter. 

#1: Life is profoundly uncertain. 

We all know intellectually that it’s impossible to predict the future. But it’s striking that the people I’ve met in my life who have been through the deepest pain and tragedy have all echoed this sentiment, that we never truly know what is going to happen. Andrew Gorbaty said it, for example, during our last interview when discussing how he got cancer at 28. 

For me, having not coped with loss on this scale yet, I just expect certainty in particular areas of my life, like expecting that certain people will still exist in ten or fifteen years. That continuity of their mere existence seems as natural as thinking…water is wet.

But Maddie’s story shook me when she described how her entire frame of reference changed when her mother died (“...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”). That broke me, thinking about that happening with my own family.

What struck me is that dealing with tragedy isn’t necessarily a fluke — we’re just lucky for all the times that we don’t. It might be cliche for me to then think, be grateful, but when I’m reminded how truly uncertain life can be, I cannot think of any other response. 

#2: Cancer is a part of almost everyone’s experience, whether you’ve had it or not. 

Through interviewing for the newsletter, I’ve started to see how common cancer is, beyond just the saddening statistics. I wasn’t expecting to write about the disease per se when I started this project, but through the more and more conversations I have (with more powerful stories to come soon on the topic), I keep seeing how many people’s lives cancer has affected: whether they’ve experienced it directly, or have a friend or family member dealing with it. 

It has repercussions on entire families, friends, workplaces, and communities. It doesn’t discriminate by socioeconomic status or what our lives look like on the outside. 

I find it tragic but also powerful to comprehend how many of us are facing the exact same issue.

#3: Speaking of communities — interdependence is crucial. 

It was interesting to me that Maddie stressed interdependence as her main suggestion to get through a difficult time. Not because it’s not important — but because any number of things could seem equally important, such as being kind to oneself, maintaining a positive attitude, taking care of one’s physical self, etc. And yet Maddie emphasized being connected to others — truly connected— as the main perspective-changer in her life. 

To me, that’s a distinct change from the way I normally think about hardship, which is: a solo experience. Something that happens to me. But looking at hardship through a broader lens — that it can be a catalyst to remembering how truly interwoven we are in the world —  makes difficulties feel less isolating. It’s why, at the end of the day, I’m doing this newsletter (and created wonderful connections because of it!). I’m doing it to remind us (and myself!) that even when we do feel alone in our struggles, we almost always are not. 

#4: Writing is a very powerful outlet to make sense of things. 

When I was speaking with Maddie, I was amazed with how well-ripened her insights were. 

Normally, I purposefully design these interviews to be conversational. I don’t want guests to feel like they have to plan what they’re going to say — I hope to just let them express themselves, and highlight their insights via the editing process later on. 

However, with Maddie, the truth-bombs were ready to go. I could clearly feel the results of how much time she had spent writing and analyzing and thinking about these topics. She has spent hours and hours and hours over the last year and a half writing about this topic every week. 

It reminded me how powerful writing can be to clarify our thoughts. 

#5: Self-kindness can help us achieve our growth goals. 

I know it’s impossible to prove cause and effect, but I strongly believe Maddie’s positive attitude toward her writing is what’s helped her grow and gain such wonderful traction in her newsletter. “I think I've done a good job checking in with myself,” she said — “anything I'm sharing is first and foremost coming from me, and not from external pressures.” 

I find that to be very inspiring, as a newer Substack writer. That success and growth in a project doesn’t have to mean slaving away and doing something I hate with the hope of reaching some future goal. In fact, Maddie has a brilliant framework for thinking about planning: reconceiving it as leaving “future gifts” for oneself, that do not come at the expense of one’s present self. 

As a natural overplanner myself, who is often resentful about always giving up present-day fun for the “future”— this was extraordinarily useful. I’ve implemented it a few times already, and have felt a bit more peace in my day to day because of it. 

And this point brings us back to the top: in that life is inherently uncertain. It’s good to plan, and look toward the future, but there are zero guarantees. 

To me, that is beautiful, scary — and freeing. 

Thank you so much to Maddie Burton for joining Celebrating Setbacks — what takeaways did you have from the conversation? Share below, and stay tuned for our next guest!