Starting Over: 5 Tips for Embarking on a New Chapter in Life

Milwaukee Central Library

Here's what I remember from Kindergarten. 1. Afternoon naps in public are not my thing. 2. Cracks on the sidewalk should be avoided at all costs. 3. To be an adult, I would need to develop essential life skills like getting out of quicksand and avoiding "the bad guys" who regularly tied non-spinach eaters to train tracks. 

For some reason, I thought a lot about trains. I thought jumping on and off moving trains would be an important mode of transportation in my adult life and that if I ever needed to take a trip, everything I could ever want or need could be contained in a bandana on the end of a stick. Never mind that, in actuality, I am the not-so-proud three-time champion of "the heaviest purse" contests at bridal showers. I remember all those thoughts, some really inaccurate things about Thanksgiving, and that Jimmy "James" Castens threw my ET hat out of the school bus window. 

Side note: I am sure his name was James, and he went by Jimmy. But whenever he was in trouble with the teacher, she would yell, "Jimmy, Jimmy, JAAAAMMMEESSS!" So, five-year-old me decided his name was Jimmy James. I can't remember my kindergarten teacher's name or anyone else in the class. (Shout out to Jimmy for having such a memorable presence.) However, I do remember what my kindergarten teacher called me. 

I was the lady of a thousand faces. No, I wasn't that lady because of my inability to control my facial expressions. (Whatever the opposite of a poker face is, that's my face.) I was the "Lady of a Thousand Faces" because I was always in the art or writing centers, telling stories in crayons. The faces were characters in my stories. 

At five years old, they were either slice-of-life vignettes with no clear point or epic adventures that seemed to have more "so then...and then...so then" than clear beginnings, middles, and ends. But then neither did Days of Our Lives, and my great grandma told us to play outside so that she could watch her program every day like clockwork, so it isn't like rambling stories don't have their niche. 

By fourth grade, I had learned that you could tell a story in words or with art, that photos were art, and that some people took pictures for a living. With that info, I decided that I was going to be a National Geographic photographer. At least, that was what I told everyone as I struggled to use my Kodak Disc camera with only 15 shots per disc at the Milwaukee County Zoo. I proudly told our chaperone that I was on a photo safari. I was distraught when the monkeys became entertained or the lion walked closer immediately after I had snapped one of my 15 available exposures. 

Maybe it's the oldest kid thing, but despite my ADHD and other quirks making me quite unconventional in my career, I played it safe. For as long as I could mark on paper, I dreamed of being a writer or an artist. I wanted to tell stories that mattered and make people think.

Majoring in art or creative writing seemed like something other than an option for me when I started college. Initially, I did what I was told to do and pursued a major in pre-physical therapy. Still, when I found it too difficult to succeed as one of 300 students in a lecture hall, I quickly changed course and settled on a Spanish major. 

Spanish was exciting because it meant traveling abroad, and while it was challenging for me, my Spanish classes were smaller. I could make friends to study with more quickly. After I graduated, I discovered that "Spanish" wasn't a job and that I really should have met with my advisor, who would have told me to combine it with something else. So, I returned to school, seeking to be a teacher. 

Teaching was an easy choice for me because I had been in education since I was a senior in high school. That year, I arranged an internship at the Curative Rehabilitation Center in the pediatric PT/OT gym three days a week and the child care center the other two. I was already comfortable working with small children as I had started babysitting and nannying for the neighborhood at ten. Yes, ten years old and in charge of nonrelative children; gotta love the eighties. (It really is a wonder any of us survived.). If I were to have kids of my own, I would have a schedule conducive to their needs. (I laugh out loud at my naivety as I write this). I managed to stay in the education field from the time I was 17 to the present.

That said, my more recent roles have been unconventional, and while they have filled my heart and soul to the brim with warm fuzzies, they have not precisely lined my pockets. Oh well, money isn't everything, right? Can't buy you love? Or happiness? Or does it? When you have enough to pay for basic life things like rent, energy, and food, when all your needs are met, you can decide which of your wants gets priority. 

As an educator, I have transferable skills. Still, I am up to my eyeballs in frustration with the bots that want me to list my years of experience in specific industries. If you are an employer looking to hire someone capable, look to a teacher. You will be pleasantly surprised by how much they have to offer. 

Talking about my new educational endeavor in this blog about living simpler might seem goofy. Still, it is part of that journey. My big reason for wanting an itsy-bitsy life (which puts less emphasis on stuff and more on time) is freedom. I want time and space to let that "Lady of 10,000 Faces come out to play again. Learning to be that lady again is part of my story, and so is having room for that kind of freedom in my life. 

Dear Miss Darling, 

If you've read this far, chances are some transition is happening in your life. You may be a new empty nester or changing careers. Perhaps you have a business you want to start (or ten businesses)? Maybe you still aren't sure what you want to be when you grow up, so you are trying to remember how you answered that question before anyone threw your ET hat out the school bus window? Whatever your journey, if you are ready to embark, grab some spinach and hop aboard for my five tips.

Five Tips for Embarking on a New Chapter.

1. Embrace All of Your Brand of Quirky.

This train is different from the ones everyone talks about. You might be laying down the track as you go because you are not like anyone else--and that's a good thing. You can comfort yourself knowing that others have stepped off the path before. All the great ones do, and you were never meant to be ordinary. The unconventional path you've taken has shaped who you are today.

What? You don't believe me. Listen, Darling, if you don't believe in yourself, the chances of convincing others is slim to none, so you had better fix that. Here's one way to spin-doctor your quirks. Make a list of things that are so 'Miss Darling' and then find the silver lining. Make that lining into an affirmation. Write it out. Reword it until it is something that you can read without cringing. There's no faking out your brain on something it's unwilling to chew on, so give it something to bite into. 

For example, here are a few things that are "so Lailah:"

• I have a lot of emotional baggage. Trauma is just "so Lailah."

• I am restless and fidgety. Not being able to sit still is just "so Lailah."

• I'm impulsive. Springing into action and putting some things on hold is just "so Lailah."

• I'm...lots of other things, you get the idea. Lailah is a hot mess.

Okay, it's time for the glitter of a silver lining and all it affirms. Here are those same Lailah traits in a more positive light. 

• Emotional baggage? Girl, please. That's not shit I am lugging around, it's my mf'ing toolkit. I survived so I could thrive with empathy, strength, and determination. My lines have been crossed, so I have had to think about where my lines are, and now my boundaries are in healthy places. I know I am not perfect, which is a gift because it means I am not afraid to fail. You seem the gymnast who gets that perfect 10, and you think that's amazing, but the really fantastic thing is how many times she fell and got back up to try it all again. Failing forward and being prepared to thrive through anything--that's so Lailah. 

• Restlessness: Yep, I am restless. I don't like to stay in the same place for too long or do the same things the same way all the time. My brain needs novelty and adventure. The irritation caused by a grain of sand makes a pearl. My restlessness propels me forward. My fidgeting helps me push against barriers and seek new experiences to grow and evolve. That is just "so Lailah."

• Impulsivity: Heck yeah, I'm impulsive. My impulsivity is just an extension of how my mind plays with ideas in real-time and space. I will take apart the radio to see why it isn't working. Is it really so bad if the radio was already broken? My impulsivity means I react with a clear head in an emergency. My impulsivity is sometimes a mistake, but it allows me to be spontaneous, to think creatively, and to find innovative solutions to problems, so Lailah!

2. Reconnect with Childhood Dreams: 

A funny thing happens to us as we grow. If you ask a group of preschool children to raise their hands if they can sing, every hand will likely rise. Fast-forward a few years, and the number of hands will decrease. Come to middle school, and you're lucky if any hands are raised at all. I already shared my childhood aspiration to be a photographer for National Geographic. 

I wanted to work there because I saw their magazine covers as striking, beautiful, haunting, and the best. The essence of that dream isn't Nat Geo (although, if you are at Nat Geo and hiring, please message me.) That dream boils down to wanting to take amazing photos and share them. It is a dream to make a living doing something creative. I have reconnected with that dream, and that's why, at 46, I chose to go back to school at Indiana University. 

Miss Darling, please remember your childhood dream. Even if it seems too impractical. Maybe you majored in something uber-practical like accounting, and you are so over your current role? If, in the 3rd grade, you wanted to be an astronaut, let's boldly go where no practical man has gone before and think about the ways that could play out in your life now--even as you approach that mid-life point. 

Am I suggesting that you be an astronaut? I suggest you consider if a spark is still there for you. Engaging with the space industry in various capacities can still provide a fulfilling and meaningful journey. You could take some courses in astronomy, volunteer, get a side job at a local planetarium, or become an advocate for space programs. You may find an accounting role at a company working with Space tourism or start a blog/YouTube channel explaining various aspects of space travel. Tap into your inner child and rediscover what truly brings you joy. Follow that joy!

3. Explore Transferable Skills: 

I mentioned earlier that it can be frustrating when bots or the people behind the bots don't immediately recognize all I bring to the table as an educator with decades of experience. Suppose you have any work experience in your background, even volunteer experience. In that case, you have some degree of skill that you have used. While each industry is unique in some respect, roles are often similar from field to field. Within those roles are skills that can overlap with other positions. Hiring a candidate motivated to succeed in a new role is worth considering. Still, it brings a wealth of experience and transferrable skills. 

As an educator, I have developed valuable skills, including connecting with people, communicating effectively, and adapting to diverse situations. These skills are transferable assets and can empower individuals in any career transition.

If you are (or were) a teacher like me, here are some additional skills you might be able to add to your resume:

• Adaptability: Educators often face unexpected challenges and changes in the classroom. This adaptability is valuable in the dynamic world of social media, where trends and algorithms can shift rapidly.

• Creativity: Educators are inherently creative in designing lesson plans and activities. This creativity can be harnessed to develop visually appealing and innovative content for social media platforms.

• Audience Engagement: Educators are experienced in engaging diverse audiences. They understand how to capture and maintain their students' attention, a skill crucial for creating content that resonates with social media audiences.

• Time Management: Educators are accustomed to managing multiple responsibilities, including lesson planning, grading, and extracurricular activities. This skill translates well into managing various social media content calendar aspects.

• Analytical Thinking: Educators regularly assess student performance and adjust their teaching strategies accordingly. This analytical mindset is valuable for analyzing social media metrics and refining content strategies based on data.

• Storytelling: Educators are skilled storytellers, using narratives to make lessons memorable. This storytelling ability is beneficial for creating engaging and impactful social media narratives.

• Tech Savviness:  Educators often use various technologies in the classroom. Their familiarity with technology, including multimedia tools, positions them well for adapting to the technical aspects of new software. 

Hey, hiring managers: Seriously, as a teacher, I had to use seven different grading platforms throughout my career, all of which needed to be more intuitive, but all were mastered out of necessity. Most teachers, especially anyone who taught online during the pandemic, have everything you need and more. If they say they've got this, believe them. 

• Community Building: Educators excel at fostering a sense of community within their classrooms. This skill is transferable to building online communities and promoting engagement among social media followers. They are often the most culturally competent people in the room because, despite what pundits would have you believe, they have a responsibility to make their classrooms safe and welcoming for all students, and they do so readily. 

• Problem-Solving: Do you need a staff member who can discern things quickly and think on their feet to encounter and solve problems? Call a teacher. Their classroom experience required them to spot and resolve student learning, behavior, and engagement issues. This problem-solving ability is beneficial for addressing challenges that may arise in any workplace. 

4. Write Your Own Story (and your own definition of success):

When I was a kid, I used to love to skip rocks. Sometimes, I found the really nice, flat stones, perfect for skipping, and even though I had what I was sure were the ultimate skipping rocks, sometimes even those rocks just plopped into the water without so much as a hop. Other times, I had a rock that everyone said would never skip, but it hopped, skipped, and jumped across Lake Michigan. 

Which throw was a success? Which was a failure? They were both successes. 

The only throws that were failures were the ones I let others talk me out of. I had no joy in setting the rocks down on the ground in a surrender of impossibility, but there was joy in every hop and every plop. 

My lungs were full of crisp air. I held the earth in my land. The coolness of the water lapped against my hand, and the fire of just one more try called to my soul. Moments like that are a perfect elemental balance of the presence of being and the persistence of memory. They are full of joy and nostalgia that never really goes away.

I can't begin to tell you how many well-meaning people I have rubbed elbows with over the years who don't think like me. They drove fancy cars and had big houses and vacation homes. They always looked put together and always had everything they needed in their purse. Their homes looked like pictures out of a Better Homes and Garden magazine. When our kidsreachedr the end of high school, they were taking their kids to tour all of the fancy schools and trying not to talk down to me when I said I wasn't pushing college as the next step forthems. 

My kiddos are twenty and nineteen now. One is in college and doing spectacularly,r and the other is already a homeowner and an amazing apprentice. More importantly, they are both kind souls who have already started to appreciate the love I have and the sacrifices that I have made to raise them to be the wonderful people they were meant to be. 

People around me tried to convince me that I needed to do things differently than I was doing them, and while their advice was well-meaning, it didn't mean much to me. Much of their advice was jarring and incongruent with my belief that children should be unfolded, not molded. 

I define my success as a parent in both my effort and how much I empowered them to have agency in their lives. I was cognizant of the gradual release of responsibility necessary to prepare a child to be an adult. I let go of the reigns incrementally until I couldn't hold on to them. That release was my success as a parent. 

It's no secret that my career as an educator was dictated mainly by my responsibilities as a parent. Those two decades were well spent developing and honing my skills while helping students appreciate languages and cultures and build literacy skills. That first career was time spent incubating for the next chapter of my life.

This chapter is where I break the mold I was cast into and finally allow myself to unfold. I will know I am successful at this when I have the freedom of time and movement in my life that I desire and I go to work to play every day. One day, someone will come to me and say that a story I told changed their life, and I will know that I made a difference. A successful life for me tips the scales in the favor of joy, no matter the external factors. 

Miss Darling, I would love to hear your definition of success. Have you found it yet? In a moment? Where you were? Where you are? Where you are going? 

5. Embrace Change with Open Arms: 

Life is full of uncertainties. Change is one of our only guarantees in this life. Everything is changing all the time, all at once. From the cells and atoms in our bodies to our minds, our relationships, our communities, and our earth, from moment to moment, everything is in flux. 

The uncertainties that come with change can flood us with anxiety. They can cause us to feel desperate to hold on to things we need to let go of or can make us paralyzed by indecision, unable to muster a sway forward or backward. Despite the trepidation, change has positive aspects. 

Suppose we only do what we are familiar with and comfortable with. In that case, we miss the chance to experience the rewards of growth and learning. Until this semester, I have had no formal training in art beyond a semester-long course in the eighth grade.

Despite my only experience painting being with paint by numbers, I did when I was twelve, ten years ago at 37 and facing my second divorce, I made a decision to go to a "paint and sip" by myself. I couldn't find anyone to go with me. I was lonely and sick of sulking at home. What happened from there was nothing short of miraculous for me. At 37, stepping out of my comfort zone gave me the courage to discover a part of me I didn't really know was there.

From that point on, I was hooked. I paint all of the time. I don't usually follow directions, but something unique happens every time I hold a paintbrush. Colors flow through me. I think in layers and blends. Like in life, sometimes I make a mess or stop just short of drinking the paint water, but the joy and the process matter most. 

Think of change not as an invitation to life and give it a bear hug. It's okay if sometimes you are holding on to dear life, leaning into your grief of who or what didn't turn the corner with you. The important thing is that you have a good grip and are along for the ride. There will be unexpected joys to be had and people to collide with. Your new purpose will find you just when you need it. If you lose your way, look for a penny from heaven or a rock shaped like a heart. You will find them if you look. A wagging tail on a dog and a good book will always point you in the right direction. 

I have to wrap up this letter now. Miss Darling, I do hope you write back to me. I would love to know about your story. Too often, I forget to ask the questions I really want to hear the answers to. So tell me your tales of change and growth or pursuing a simpler, more fulfilling life. 

Our journeys are ongoing like the "Lady of 10,000 Faces." Remember that you are the one holding the crayon in your own story. 

Please come back to hear more of my thoughts about how I am trying to find my way to my dreams. As I write, I am peeling back layers, nurturing the parts of my life that sustain me and getting rid of the things that hold me back. I am cultivating resources like confidence and learning to be minimalist to make that more straightforward to achieve. 

With love, 

Lailah

P.S. Adjusting to school again has been easier than I thought. I took some simple steps to organize my calendar. I take one assignment at a time and prioritize project steps the same way I do at work. So far, I have managed well enough. There's no big secret to the balancing act for me now except my passion for the content. 

Last week, I had my first big photography assignment. I want to share some of my favorite images from that assignment. 

I would love to hear your thoughts on my work.