From Blackboard to Bourbon ~ Overcoming Fear of Crazy Ideas and Beginner Mistakes

When I started teaching at 45, I made and laminated two signs that decorated my classroom for the entire 14 years of my second career. One was a large banner, adorned with hanging silver-painted Styrofoam balls, that stretched across the doorway into the classroom. It read, “Caution: Imaginations on the Loose.” The other was a poster that read, “A Mistake is a Risk You Take and Learn From.”

I’ve been reminded of both these homemade signs since I retired two years ago at 59. I let my imagination loose as I contemplated, and then did, a 70-day trip around the world as a first-time solo traveler. I let my imagination soar to a plan to move to Portugal before I turn 65. My loose imagination led me to start blogging for the first time three months ago. And I gave imagination free rein when I wondered if I could learn about the production of bourbon whiskey — my favorite distilled spirit — as an over-60 unpaid intern. After I successfully proposed my Midlife Reimagined Apprenticeship, someone on Instagram asked if it was a real thing or just something I thought up. I responded that it was something I thought up, and now it’s a real thing.

Isn’t that how it’s supposed to work? We give our imagination permission to roam untethered, we think up a crazy idea, and then turn the crazy idea into a real thing. Yeah. That’s how it can go, if we don’t let fear get in the way.

I sat on my “apprenticeship” idea for months, using the pandemic as a reasonable excuse at first. Then, I wondered if perhaps I really just feared no distillery would be interested in letting a 61-year-old female, arthritic, retired teacher work on a distillery floor. I’d done enough research to know that distillery operations involve heavy, dirty, potentially dangerous manual labor. There’s a titanium screw holding my right shoulder and bicep together. What if I couldn’t do the work? What if I couldn’t keep up? I have zero background in the distillery business, and any company agreeing to train a completely inexperienced newbie is taking on added responsibility and commitment of time and, therefore, money. What if I screwed up? What if I ruined some whiskey? What if I embarrassed myself?

I almost didn’t reach out to the CEO of Cleveland Whiskey, but when I did he was immediately receptive to my wacky idea. His company’s slogan is Whiskey Without Limits. How perfect a match is that?! Let’s hear it for Aging Without Limits…Midlife Women Without Limits…Retirement Without Limits…Authentic Living Without Limits. Yeah!

I can’t believe I almost let fear of my own wild imagination — and fear of rejection? — get in the way of this opportunity. That isn’t the way it’s supposed to go, but we know it is the way it sometimes does go. I talked about almost letting fear derail me in this week’s Reinvention Rebels podcast with Wendy Battles. Why do we let fear do that? And is it more prevalent among women than men?

Now that I’m in week three of my 12-week whiskey internship, I’m constantly reminded of my young students and my classroom Mistakes sign. I’m the only woman and the oldest person on the distillery floor. The guys there are terrific. They are patient and welcoming. My primary trainer is a fantastic teacher, breaking apart tasks in sequential, bite-sized modules using a straight-from-the-classroom I Do, We Do, You Do format. He gives descriptive feedback and encouraging praise, and when I f*ck up — which I definitely do — he lets me, then lets me figure out what I did wrong. A mistake is a risk you take and learn from.

Blackboard to bourbon Venn diagram
Working at the distillery reminds me of my teaching days in some ways.
(No…not the drinking part.)

Most importantly, he told me to stop being afraid. Not afraid of physical harm, but afraid of making a mistake and breaking something. Or looking stupid…or worse. (That ship sailed when I mistakenly headed to a garage door thinking it was the freight elevator. Or, when he explained a siphoning tool used after the filtering process. It’s called the “jack” but, based on how you operate it, I thought he added a second word — the opposite of “on” — after the tool name. So I later asked about using the “jack off” and…well…not good. I have not been summoned to HR yet, so I guess that is good.)

Despite these flubs, my trainer said he’d give me a B+ grade at my second week. He reminded me — as I’d reminded my students — not to lose confidence, because mistakes are how we learn. Of course I know this, preached this, as a teacher. But as a student, a true beginner, it’s easy to forget. I want an A grade.

As I wrote in this blog post, Tom Vanderbilt, in his book Beginners — The Joy and Transformative Power of Lifelong Learning, stated that being a beginner at learning a completely new and different skill requires one to become comfortable with being uncomfortable. You have to become comfortable with the discomfort of making rookie mistakes and looking like a dumbass. It’s gonna take a while to get that A.

I’m learning a lot and having a blast, but this is still new territory for me. The guys assure me that the mistakes I’ve made are normal and to be expected. But still… As a teacher, I was used to multitasking and doing 15 things at once. On the distillery floor, tasks overlap and procedures flow very quickly, too. I am still going very slowly, referring to my written notes, and going step by step while talking to myself (out loud) and reviewing a checklist in my head multiple times. I’m resisting the second-grade teacher need to label, color-code, and attach Post-it Notes to everything. I’m not yet ready for overlapping and multitasking. It takes me longer to empty a barrel, clean a tank, connect and disconnect valves and hoses. Just like my students, if I try to rush through a process so I look smarter than I am, I fumble. As I always told my students: “Slow down, and be sure to always check your work.”

Something I did get right the first time was flipping a bourbon barrel. Even empty they are heavy AF.

Having fun is also part of being a brand-new beginner. Vanderbilt is right. There is absolute joy in learning a new skill…in going from not knowing to knowing. Vanderbilt committed to learning five new skills: surfing, singing, drawing, juggling, and chess. I’ve committed to learning Portuguese, whiskey distilling, HTML 5 coding, and golf. My beginner golf lessons start next month. It’ll be interesting to see the reaction when I show up to my first lesson straight from the distillery and smelling like bourbon. I can’t wait.

Having Fun With More Teaching & Distilling Comparisons

💜Thank you to Canadian blogger Writer of Words, Etc for giving The Hot Goddess and my handy charts a shout-out! These are for you:

Taking work home takes on a whole new meaning as a whiskey intern.
An unrelated side benefit of being a whiskey intern at 61. Just saying.

What do you want to learn as a beginner? Has fear of making mistakes ever held you back? Has fear that your imagination was a little too out there ever stopped you from pursuing an idea? Isn’t turning your back on overthinking, and just giving yourself permission to go the f*ck ahead and do it anyway, simply amazing? A mistake is a risk you take and learn from. Give your imagination permission to fly free.

All images from retired_rewired_inspired.

If you enjoyed this please remember to Share, Like, FollowComment, Subscribe. (This is my “call to action” I’m supposed to include in every post. Thanks so much for your support!❤)


  1. Sounds like you are having lots of fun. Congratulations on being brave enough to give it a go. I do wonder where all the female fear comes from. We women overthink and talk ourselves out of so many things because we are afraid while most men seem to confidently jump into things without a second thought. Enjoy the bourbon!

    Liked by 1 person

  2. Excellent! I’m inspired. Right before the pandemic lockdown last year, I was on the path to learning to scuba dive with a goal of getting my certification. And then all the pools shut down. Time to get back out there. I’ve got work to do👍🏾👍🏾🤿

    Liked by 1 person

  3. Awesome post this week! I’ve been waiting to hear how the internship was going. There’s a chocolate place near by here, I wonder if they’d let me intern there. Looking forward to the next “instillment” of your blog!

    Liked by 1 person

  4. I am very impressed by this entire post. You inspire me! Believe me, I need it, especially these days…

    Did you know my mantra is If Not Now, When? This is something that I cooked up when I turned 50 a couple of years ago, and I learned, painfully slowly, how to let go of fear. So much so that I wrote a kinky blog under a pseudonym, then self-published a kinky book, then released it, then came out and let my pseudonym be known (but I still hesitate advertising it too much…)… and now I’m writing more books which I will release (eventually) – but probably not kinky ones. THEN, I posted selfies on social media (I never did that prior to turning 50), talk into video (ugh) on social media, and I continuously hurl my words out onto my blog on a daily basis (as you know).

    Seems fear, which is still deeply rooted in me, is taking a smaller space up within me. Oh, and the tarots have helped me to tune into my intuition better. Now, the only thing left to do is to get income in some way or form (and since we’re STILL in lockdown, it will have to come from this keyboard).

    So, thank you for inspiring me, and for connecting with me! I look forward to more fun and shenanigans… 🙂


    • Thank you so much!❤
      I love your mantra. So true, and so hard to do at times. Brava to you for your badass courage to go forth with kinky writings! Would love to read your work. And kudos for now writing more books and expanding. YOU are inspiring!💫
      I too am a social media newbie. I avoided it all until I was 59. Never blogged until 61. It’s scary, but making connections like this with you has changed everything for me.
      My confidence and boldness are growing — though I have my moments of overthinking and self-sabotage.
      Thank you for your comment, and your encouragement❤


      • My book is on my website on the book tab, written under my pseudonym. 😉

        I was a little obsessed with kink for a while, and when some of the chapters appeared on a blog (the pseudonym one) I got quite a bit of feedback both in comments and privately in email (I took it off since I released the book) which is why I crossed the threshold from discomfort to “just do it”. 😳🙃

        Liked by 1 person

  5. You’re just incredible! And I’m so glad those guys u work with sound so great. Although I can’t help but think that your presence there is actually also teaching them a bee level of respect for women!! You’re such a goddess 💖🌸💖🌸

    Liked by 1 person

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