Choices Over a Decade: the gifts and regrets

I started reading The Midnight Library this past week. It’s a book about regret and choices (and maybe more, but I’m not done yet). The main character, Nora Seed, has the opportunity to experience the lives she would have lived had she made different choices.

She’s made a LOT of decisions that she has deep regret over.

The story is fascinating because she gets to see what her life could have been had she decided differently.

We all have those regrets about some of our decisions, don’t we?

We make the best choice that we can at the time, but later we look back and wonder WTF we were thinking. We fall into regret and spend far too much time wondering what could have been.

So far in the novel, the glimpses into those “missed” lives aren’t at all what Nora imagined they’d be.

The story has made me ponder the whole idea of regret and the decisions I’ve made over the past decade as my life has changed from teaching full-time while coaching speech & debate and having my two teens at home, to being a published writer and running my own online coaching and writing business as an empty-nester.

Would I have made different choices? Would you?

I have regretted some decisions over the past decade, but even those have brought gifts and wisdom. And if there’s one thing I’ve learned over the past fifty years, it’s often in our challenges that we find ourselves and the wisdom and lessons we need.

One thing I am eternally grateful for is this blog and how it’s been a record of many of these lessons I’ve learned. It’s like a living record of my writing, lessons learned, and the paths I chose to take. It also helped me to learn to express myself and develop my voice.

Looking Back at my Life

In looking back at my own life as a writer/entrepreneur over the past decade, I like what I see. It’d be a different list if I focused on my relationships, health, or spirituality though they’re all intertwined in many ways.

  • Started writing and managed to finish several novels, land an agent, but ultimately self-published my work
    • The gifts: I learned that I can write and have accepted that I’m a relatively slow writer! I also really like being an Indie writer and self-publishing my work.
    • Regrets: None! This is definitely the right path for me.
  • Developed and grew a website for teen writers which I closed after several years.
    • The gifts: I learned that I can handle tech and build websites. I find the visual and strategic parts of that fun.
    • Regrets: Despite building up Where Teens Write to almost 300 members, I was terrified of marketing myself, being seen, and putting myself out into the world in a bigger way. What would people think?!? Rather than figuring that piece out, I closed it. I wonder had I stuck with it, what it could have become?
  • Left the classroom after teaching English & Creative Writing for 15 years (12 at the HS level and 3 at the college).
    • The gifts: It took stopping teaching to learn that I’m a teacher at heart. I LOVE working with and teaching clients both 1:1 and in small group programs. I really missed the students when I left. It’s funny – most people assume I left because of the kids, but they, in all honesty, were the best part of the job.
    • Regrets: NONE! Sorry (not sorry) SCHS – it was great while it lasted, but it was definitely time to go!
  • Launched a successful (with a waitlist) web design business so I could leave the classroom, work from home, and have time to write (bahahahahaha!). This is the one path that I wonder about – had I quit teaching and focused on writing rather than Entwine Web Design, where would I be? Would I have more books published? I don’t know, but even though this path feels like a bit of a detour, it still offered lots of gifts.
    • The gifts: I learned that launching and marketing a service-based business is NOT the way to get more creative time in my life. More importantly, I learned how to market myself and how to be comfortable with being visible. It took a LOT of work to get past my fear of judgment and what people might think. I’m now pretty much 95% over that. People will think whatever they think, and I have absolutely no control over it, nor do I desire to have any control over it. I’m going to do my thing.
    • I worked with incredible women who I am now honored to call friends.
    • I also learned that tech is not where I want to work – words and language and creating is my zone. I had that right by going into the classroom for my career, but I need to teach and work with people on my own terms, not those that the public school system demands.
    • Regrets: While the gifts were many, I didn’t focus on my own writing at all. That got pushed the wayside as I learned other important lessons around building a business, marketing, self-confidence.
  • Closed my web design biz to new clients and returned my focus to writing and teaching. I revamped my website and blog and started working with clients who have big ideas but need help getting them developed, structured, and created/written. So far, no regrets here.

I love it.

Looking Ahead

In my very first blog post ever, I claimed that I am a writer. At the time, I already identified as a writing teacher but wanted to claim my voice and identity as a writer.

I didn’t realize I would let that identity play second fiddle to my identity as an entrepreneur in the online world, a web designer, and a tech VA (of sorts).

Now, I’m OWNING that I am all of the above: a writer, a writing teacher and a book coach (that’s the entrepreneurial piece in me).

I always have been. I always will be. It’s where my heart is (though grading and grading and grading and grading some more made me forget how much I love helping people express themselves and find their authentic voice).

I’ve come full circle. And I’m excited to see where I’ll be at the end of the next decade, in the winter of 2031!

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