Stepping Back in Order to Move Forward – How I Decided to Bet on Myself
Guest Contributor: Erin Robertson
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Remember in the fall of 2020 when we started hearing the staggering statistics about how women were voluntarily leaving the workforce in droves? Politico.com reported that 863,000 American women left the workforce in September, 2020 alone.
*Raises hand*
I was one of those women.
In September, 2020, I was, like so many others, burned out. Which was odd, because in many ways I was exactly where I wanted to be. I was a Director level employee at a prestigious Napa winery with a loving husband, a young daughter, and a small wine brand that my husband and I ran together.
I had spent the prior 15+ years carving out a career for myself that I was really proud of, but most days I was exhausted, had trouble focusing, and felt at least low-level angry at one thing or another. Of course, the added stress that COVID had introduced into everyone’s lives didn’t help. Childcare hours had shortened (if they existed at all), we were completely cut off from seeing any of our extended family, and we were questioning if we even wanted to live in California any longer.
Even though I had fantasized about freelancing for the past decade, I had always been afraid to take the leap. While I relied on and enjoyed the stability of the regular paycheck and benefits, working full time for someone else began to feel stifling, and even more so since becoming a mother. I struggled with feeling like my time and schedule belonged to someone else. I constantly snuck out early, hoping no one would notice, or “worked from home” because I just couldn’t sit in an office for that long. (Sorry, former coworkers!)
Working full time for someone else had become unsustainable, yet quitting my job and having our family be down an income seemed impossible.
And then something happened. One day I had a particularly challenging meeting at work, and a lightbulb went off in my head - I was DONE. I knew in that moment that the next day I would resign from my job, with nothing else lined up. This was the moment that I was going to branch out on my own.
For the first time, the way that I was feeling (awful, all of the time) started to take precedence over the stability of a paycheck. I knew I needed to take a step back to clear the noise in my head and find myself again - the new version of myself who was now a wife and mother, who no longer had an egoistic attachment to job titles and big-name companies, and who was ready to forge her own path and bet on herself.
So now that I was ready emotionally, it was time to get down to logistics of how life would work moving forward as I embarked on the world of self-employment.
I took inventory of my situation.
On one hand, I am not wealthy, my husband and I contribute equally to the household expenses, and health insurance is a real and valid concern.
On another hand, I have 15+ years of industry experience and a robust network I’ve worked hard to cultivate. Our small wine brand, though nowhere near generating an income stream, was doing well and experiencing growth (even during the pandemic). I also had confidence and clarity around my own knowledge and abilities, and what value I could offer clients and our own brand.
Financially speaking, I had decent amount of savings that I knew I could live off of for many months. Crucially, I had an emotionally supportive husband who wants for me to be happy and succeed in the way that I want to for myself. (His attitude around me leaving my job was always, “Quit if you need to - we will make it work.”)
Fast forward one year, and a lot has changed. We have moved across the country to central Virginia, and have decided to, in addition to both consulting for small wineries, throw ourselves into making our small wine brand, Dogwood & Thistle, a financially viable business for our family. I took a few months off of working altogether (except on D&T) and focused on resting, resetting, and figuring out exactly what I wanted my path forward to look like.
I initially had a bit of fear that if I didn’t dive right into freelancing, or strike while the iron was hot, that I would quickly lose momentum and contacts, but I decided to trust myself, and trust that I would still be able to do what I wanted to do after a few months off. I’m so glad I did, because that time was invaluable to me, and when I did start working again it came from a place of genuine desire to be of service and contribute to the world in that way, not from a place of desperation and sadness.
Right now, I’m working freelance with a few select clients on DTC-focused sales and marketing initiatives. I’m able to take time to exercise, plan trips (COVID-style) and be present for my daughter on my terms, without feeling like there is someone watching my back and counting my hours.
If you are also feeling burned out and are thinking of taking some time off, I strongly encourage you to organize your life so that you can do it. Here are some things to be sure to have lined before you jump off:
Enough savings to live for 6 months to a year without bringing in any income. I know that this can be very challenging, especially if you live in an expensive area, but it is crucial to start developing this financial foundation.
Knowledge of your state’s unemployment laws. In some states you are able to file for assistance even if you voluntarily leave your job. Do the research, and don’t be ashamed to file for benefits if you can get them. You have paid into the system, and it is there to support you.
A strong understanding of your monthly spending, and of what spending you can cut back on during your time off. For me, the first things I cut out are new clothes, buying books, and eating lunches out. Side note – childcare is NOT something I cut out during this time. Our daughter continued to go to her pre-school every day so that I would have time to decompress and work on some passion projects. I have no regrets about continuing to spend that money monthly.
The support of your network, whether that’s friends, family, professional network, or all of the above.
The willingness to suck up the health insurance piece of it. There is no getting around the fact that the health insurance piece of this sucks, but at some point, paying for your own health insurance becomes less painful than staying in your current situation.
A strong enough professional network to feel confident that when you are ready to return, you will be able to do so. There is no shortcut to this. You have to have worked hard to build it for yourself over the years.
Have you made a similar life change recently, or are you hoping to soon? If so, I’d love to hear from you! Please reach out on Instagram or via email so that we can chat.
Erin Robertson is a wine industry sales and marketing pro with twenty years of working in the wine industry in various capacities. She holds a certification from the American Sommelier Association in NYC, and a wine industry focused Executive MBA from Sonoma State University. After living in Napa Valley for thirteen years, Erin is now living in Charlottesville, VA with her family. She and her husband run two companies together – Hally Wine Company, a full-service wine industry consulting company, and Dogwood & Thistle, a small wine brand making wine in Northern California, and soon, Central Virginia. You can connect with her via email at erin@dogwoodthistlewine.com or on Instagram @erin.e.robertson.
What We're Reading:
Here's what has piqued our interest this week in the world of wine and mindfulness.
Don’t Wait for the Weekend: Five Ways to Take Care of Your Mental Health at Work Today – Chopra.com
Oftentimes we search for meaningful work that fulfills us, or we strive for work-life balance trying to avoid burnout. These are admirable pursuits, however on their own they aren’t enough to support our mental health.
How We Get Hooked By Shenpa - Pema Chödrön for Lion's Roar
Shenpa is the urge that triggers our habitual tendency to close down says Pema Chödrön. We get hooked in that moment of tightening when we reach for relief.
It's Time For The Phrase "Working Mom" To Go – Romper.com
The mommy wars have long pitted working mothers against stay-at-home mothers but these are models that no longer hold up. Let's embrace the idea that all of us have work and care responsibilities
How to Be Mindful When It Matters Most – Shalini Bahl-Milne for Mindful.org
Finding your flow and living authentically comes from a place of mindfulness, explains Shalini Bahl-Milne—we just need to be willing to stay with both the good and the messy aspects of our lives.
NEW Episode: The Fine Line Podcast - Episode 26 - Christopher Russell
For the latest episode of The Fine Line Podcast: Balancing Hedonism & Health, the team speaks to Christopher Russell about his experience of pursuing mental health personally and professionally during his 40 years in the restaurant and beverage industry, as well as his transition to leave restaurants and become a full-time psychoanalyst.
The Fine Line Podcast is co-hosted by Lisabeth Danneels and Emily Gold. Even the sub-title (Hedonism & Health) indicates the commonalities with A Balanced Glass. Please check them out!
