Joanna Guldin

Co-Host and Co-Founder of PILLAR Deployment Retreat

Service Member's Branch - Navy

Service Member's Status - Veteran - 6.5 years

What has been your military spouse career/entrepreneur journey so far?

In 2012 I began writing Jo, My Gosh! when my now-husband deployed to Afghanistan for a year. In 2013 we got married and I moved to be with him, giving up my teaching career because of licensure difficulties and began freelance writing for a variety of organizations and businesses. From 2014-2016 I grew Jo, My Gosh, continued freelancing, consulting, and working full-time in the military community while we saved for my husband's separation from the Navy. Then in 2016, I helped my husband open Swatara Coffee Co., an IRL coffee shop that we grew to two locations in 5 years. I began working for Military.com as a Social Media and Community Engagement Manager and worked with Becky Hoy to launch PILLAR Deployment Retreat in 2019. We Sold Swatara Coffee Co. in 2023, and in 2024, PILLAR Deployment Retreat celebrates 5 years and Jo, My Gosh! celebrates 12!

Tell us about yourself.

Joanna Guldin is the social media and community engagement manager at Military.com. She has worked in the military community for more than a decade, and her writing has been featured in national and international publications. She lives in Pennsylvania with her Navy veteran husband.

Tell us about a "typical" day in your professional life.

It's so boring! I wake up, feed our dog, eat breakfast, and then get to work on my to-do list!

If you've been stationed overseas, how did this affect your career and or business?

N/A

What has been your biggest military spouse career struggle and how did you overcome it?

At the beginning of military spouse life, I had really no template for how to freelance or network, so I learned as I went along. Looking back, there are so many things that I could have done to make my life easier... I just didn't know!

What role did mentors and sponsors play in your journey?

Wonderful military spouse entrepreneurs like Adrianna Domingos-Lupher and Krystel Spell were so welcoming, warm, and helpful as I began my freelancing career. They spoke my name when I wasn't in the room and continue to be treasured people in my life-- even now that I'm old hat at this freelancing game! PILLAR is grateful to have the support of USAA Life Insurance Company and USAA. They believed in our idea before we launched and have been stalwart collaborators and amazing people to work with over the past five years.

How does your career path differ from what you imagined for yourself?

I thought I'd be a teacher for 40 years! I do miss teaching because I truly loved it-- it was a dream career for me-- I've also had the opportunity to do some really cool things through my writing career. That includes actually being paid for writing (which was always a goal of mine, even as a kid), interviewing (and sitting next to!) Rob Riggle during an Army-Navy Game, being invited to and visiting the White House, and being invited on numerous trips and experiences because of my work with Jo, My Gosh! and Military.com.

How did military life (PCSing, deployments, trainings, etc) factor into your career decisions?

The hardest decision was to leave teaching and not renew my license. Because of my husband's career schedule (moves, C School, etc.) it just didn't make sense for me to renew a license in another state with the possibility of moving quickly after. We were newlyweds, too, and didn't have a lot of money to spend on a license that probably wouldn't be useful in a few months.

Have you ever had to geo-bach due to your career/entrepreneurship?

N/A

What resources have you found to be useful in your career/entrepreneur journey?

Networking with people online! I love that I can take my military spouse community anywhere. Those connections have been invaluable-- whether it's for moral support, brainstorming, or even finding new jobs, it's a community that isn't geo-located.

Final word: what are your top tips for other military spouses about navigating a career within the military lifestyle?

I'm so glad that I continued to work, even when I was technically unemployed. Because I was contributing financially to our household, we were able to bootstrap a business entirely ourselves (which gave us freedom to do things the way we wanted to, rather than being held to standards or schedules outside of our control). We had a very easy transition from military life to civilian life because I had an income and health insurance we could lean on while my husband was between the military and launching our business.

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