When work feels like a dead end
Welcome to Wisdom Wednesdays from Owl & Key
Each week, enjoy a quick guided reflection to help you unlock what's next and bring your Strategic Plan for Life into reality.
Let's dive in!
A quick note on today's post:
There are so many people in this community and beyond facing layoffs, career uncertainty and business change. So in true Owl & Key fashion, we want to share real stories of real people living through these exact experiences with intention - and what they did to move through it.
Erin Shems, one of our Expert Guides, was kind enough to share her personal, behind-the-scenes journey of when she hit that moment herself and what she did to move into her next chapter.
For those feeling really strong and stable in your careers and businesses - save this for future reference if you ever need it. But for those of you in a similar spot, we hope you find comfort, clarity and community through Erin's story.
Thank you, Erin, for your MANY generous contributions to this community. š
From Erin:
Back in 2023, I felt like my career was heading towards a dead end.
I knew something needed to change ā so I started doing all the things people suggested like...
Networking with other teams within the company,
Creating a new job description for a role that the team was lacking,
Taking on a bunch of āstretchā projects,
Volunteering for thingsā¦
Nothing was working.
If anything, I was running myself even further into the ground.
When It All Piles Up
During this time, my former employer (spoiler alert) offered a program for managers called Strategic Planning for Life (SPFL). I learned that Owl & Key wants to help others design and live what they call an Intentional Lifestyle ā a life based on who we are as individuals (meaning our values, purpose and goals).
It piqued my curiosity and between the constant shit show at work and feeling like my career was heading towards a dead-end, I knew something needed to change.
I signed up.
Little did I know, Iād be dealing with a ton of personal things before the course started and almost bowed out.
I was trying to find an assisted living facility for my disabled mother, get her moved in and situated, before leaving the country for two weeks for a trip of a lifetime with my husband. Take all that stress, multiply it by 100 with everything going on at work and voila ā not much gas left in my tank.
I decided to login anyway for the first session. As soon as I shared why I signed up for SPFL, I broke down in tears. What an introduction. It was hard just showing up that first time, but I stuck with it.
The Reckoning Moment
It appeared there wasnāt much I could do with my career ā nowhere to grow at the company, couldnāt land an interview, and the burnout was getting even worse.
Turns out, itās a bit like the scene from the Wizard of Oz, where Glinda tells Dorothy, āYouāve always had the power, my dear, you just had to learn it for yourself.ā
It was up to me to create choices and seek out other options. My employer wasnāt going to do it for me.
The Choice
After 7+ years of being a dedicated employee, I was done chasing the titles and climbing the ladder.
Many people are feeling this these days. Loyalty doesnāt pay off like it used to ā it doesnāt always end the way we envision.
I decided Iād rather scale back my lifestyle to spend more time with people I love, doing things I love, before weāre gone.
I needed to return to myself ā find home again.
Turns out, you donāt need ruby slippers to find it.
An Aligned Path Forward
Little did I know, the work I began in that SPFL workshop in early 2023 would have a direct impact on my walking away from corporate and a 29-year career to start something Iād never in a hundred years have thought ā founding TWO businesses (Ezippy Co. & The Recess Reset) ā but here we are.
While I no longer have the corporate paychecks, I also no longer have the annual reviews or the pressure to perform for shareholders.
I donāt sit through non-stop meetings, skip meals, or stress out about stupid things that really donāt matter.
While I do miss the paychecks (money does equal freedom in many ways), I donāt miss much else besides a handful of people.
By doing less, what do I have more of these days?
The ability to rest more, define what my days look like, more breaks, more autonomy over whom I spend time with, more room to write, create, and explore, more time to invest in relationships, and more freedom to build things so I can help others in the same situation I left behind.
Things that I didnāt think were possible are happening. For instance, I was on stage October 11 at the AIGA (American Institute of Graphic Artists) Design Conference in DTLA (Downtown Los Angeles) giving a talk about depression to a roomful of designers alongside my art director friend/colleague.

See the full LinkedIn post here. š
The Intentional Exchange
Yes, it requires sacrifice to make this leap: cutting back, spending less, traveling differently, eating at home way more, being frugal, driving older cars while I build something from nothing, but guess what?
Iām so much happier, healthier and actually enjoy the work Iām doing.
Every day I appreciate HOW I choose to spend my time and energy.
Even when life throws me a monkey wrench (radical acceptance has helped a lot here), I still donāt regret making the leap.
That Strategic Planning for Life course helped me close a chapter and start several new ones. I choose to do less in order to do more meaningful things that are aligned with who I am.
And thatās why earlier this year, I trained to become a certified Strategic Planning For Life⢠Guide ā so I could help others design and live an Intentional Lifestyle.
And hereās another cool thing I couldnāt have imagined doing a year ago:
Owl & Key is offering a new course called the Corporate to Entrepreneurship Program: Making the Intentional Leap and Iām co-leading it alongside Krista.
Program begins January 22, 2026 (we moved it to the new year so we all have one less thing in 2025).
Hope to see you there! New year. New you?
You got this.
Erin
Have questions for Erin or want to share what resonated? You can email her here: [email protected]. š
Other offerings for 2026 & beyond....
If you're a leader trying to be more intentional with your family, your team, your time and priorities in 2026...
- Connect with our founder Krista ([email protected]) to explore a 1:1 Strategic Partnership, Retreats, Programs and Workshops.
If you're a Community Member or in a current Strategic Planning for Life Class...
- Bring your reflections from this email to the next Community Call or Class session to share with your Guide or a friend.
If you or someone you love is interested in entrepreneurship and want to make 2026 the year of an intentional leap...
- Join us for this upcoming live program - kicking off January 22!
If you're a DIYer and just want to dip your toe into being more intentional going into 2026...
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