8 Questions for... Kim Druker Stockwell

Women's Survival Guide

Photo by Claudio Schwarz on Unsplash

I live in Boston with my husband, and though our three “semi-launched” daughters have flown the nest, I can’t help but miss the delightful chaos of our 20 years under one roof together. Now, however, I’m riding a fresh wave of creative energy—ready to do, make, and go! Life, it seems, is serving up a deliciously unexpected second act.

Over four years ago, I started Women’s Survival Guide with one goal: to motivate women (and myself) standing at life's crossroads. Midlife is a funny time—it often leaves you asking, “Now what?” and “Who am I if I’m not the role I once played?”

This little corner of the web is our shared journey from “now what” to an exhilarating “what’s next.” Through personal stories, inspiring interviews, and practical advice, I hope we can uncover fresh ideas, ignite new passions, and embrace a renewed sense of possibility. After all, our stories aren’t over—they’re just evolving.

When I’m not swept up on Substack, you can catch me painting at my studio in Boston’s SOWA arts district (450 Harrison Ave—pop in on First Friday!). I also love to cook, garden, and play sports, and I have an enduring affection for British humor and Japanese fiction.

1. Why Substack?

A friend of mine in Cambridge (MA) who is in the tech world was reading my blog, which was just a website I made on Wix, and suggested I check out Substack. He thought it would relieve me of managing the technical part of maintaining a website and my subscribers. He was right!

That was in Feb 2021. I brought the five posts I had already published to Substack right away. I liked that my work achieved a uniform and professional look. On Substack there are choices but not so many that it is overwhelming, design wise.

2. How long did it take you to find your groove?

I found my groove right away as far as publishing goes (every Sunday at 4:20 AM) and that was four years ago. But, it took me over three years to understand I need to connect with the community of Substack to grow in a meaningful way. Through commenting and reflecting on others' posts and then on Notes, which I honestly am just getting really into, I am enjoying the community far beyond my own work. It makes a huge difference! Duh.

3. How has it changed you?

The work is addictive for me even if no one reads it, though they do. I have a sense of discipline and responsibility to what I am trying to do, which is a good thing for an empty nester/midlife maven to have in her life.

4. What mistakes have you made?

Not getting involved in the wider Substack community for years.

5. To pay or not to pay?

I am still struggling with that. I work hard on my interviews and posts. I do not have a lot of paid subscribers. When I have a paywall, I think about how few people will read my work and then, what's the point? Also, I am trying to do something that isn't about making money. Why am I trying to charge for it?

I think what I may do is: stop having a "premium" level (paid), still allow for people to pay if they want to, work towards 5,000 subscribers and get an advertising gig (tastefully done) to offset my expenses.

6. What artistic and technical choices have you made?

I designed my logo on Wix. I like it, and others seem to, but it's in need of an update.

I am a painter, full time (www.kimdrukerstockwell.com). Artistically, I have not been able to integrate my art into my Substack. The two compete visually. At the suggestion of a professional editor, I will start using my favorite work as the basis for a new palette for my Substack and I hope to use the Little Women I paint in my Notes posts. That's the plan.

7. What’s been the effect on your writing?

The more you do of most anything the better you get and it's certainly true of writing.

8. In it for the long haul?

Absolutely. Women's Survival Guide will age with me. The focus will shift as mine does.

I like to bring in fresh, professional eyes every now and then to refocus my work. I am about to do that now.

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Kim Druker Stockwell