Every Little Step I Take is Magic
What I’ve Learned From a Not-So-Linear Career
Lately, on my podcast Well…Adjusting, I’ve been chatting with a lot of folks about careers. One thing that keeps popping up is the struggle with imposter syndrome and how to keep believing in yourself, even when rejection just keeps on rejecting. Through all these conversations, one piece of advice seems to stick—every step you take, no matter how small or seemingly off-track, leads you to your next move.
There are no mistakes.
I really believe that. Looking back at my own (let’s call it winding) career path, every job I’ve held—good, bad, or downright sad—has brought me to where I am today. Where is that, you ask? Well, hopefully, poised for something really great. You hear me, Universe? I’m poised. Let’s go. Snapity snap.
I’m not saying I took the straightest, smartest route to where I am today. If anything, I’ve meandered, zigging and zagging from “college grad with no clue what to do” to “actor, writer, producer, podcaster—who maybe hosts too many podcasts.”
Let’s take a look at some of the jobs that got me here, shall we?
1. My first job post-college was at a Cheddars restaurant (think Bennigans, but in Texas). Sure, I had aspirations of greatness coming out of college, but I graduated in the middle of a recession. I had no idea what a recession was, let alone the fact that we were in one. I changed my major approximately 1000 times in college, but never to finance. All I knew was I couldn’t land a job anywhere. Even folks at the mall were making that “I’m not hiring you face” as they said, “We’re really looking for someone who has experience selling housewares.” But, somehow, my charm and wit landed me a job as a server at Cheddars.
There, I learned that I don’t have the ability to juggle 14 tables at different stages in the ordering process, and people aren’t happy when you drop a pitcher of water on their lap. I also learned that knowing what you do and don’t do is essential. If you’re in a job not aligned with your skill set, it’s time to move on, buckaroo. Also, don’t use a kitchen rag to wipe water off an old lady after spilling water on her. You’ll accidentally touch her boobs. She will not care for it.
2. Next, I sold sneakers at Lady Foot Locker. Humbling is not quite the right word for a work uniform consisting of a polyester top with green referee stripes paired with high-waisted khakis, but it’s pretty darn close. I quit after the regional manager told me I’d be pretty if I wore more makeup.
There I learned that I stink at sales. I don’t like upselling shoelaces, overpriced socks, or trying to jam someone’s size nine foot into a seven because the smaller size makes them feel better. More importantly, I learned that what managers think of you matters. Managing up may not be fun, but it can make or break your career trajectory.
3. Next, I moved to the glamorous world of temporary jobs. I’m not sure temp jobs are still a thing, but back in the day, there were agencies that would get you gigs covering for a receptionist or secretary who was out on vacation or maternity leave. All you had to do was find an agency, take a typing test, and call them every morning until they had worked for you.
There, I learned one of my main work philosophies: don’t be an idiot. At these gigs, I showed the most basic level of competency and was lauded like a queen who had come down from a mountain. It was a regular occurrence to be offered a full-time job. Speaking of which, my last temp gig led me to my next job at…
4. BLG & R&D Installers. That’s not exactly the name, but I’m fairly certain that all the owners of this company were connected, so let’s go with it. This job was at a shipping and delivery company for office cubicles. They brought me in for a week to cover for the receptionist, who I could only assume was heading out to catch multiple legs of an AC/DC tour. Her hair was huge and very feathered. Despite answering the phone, “CFR&D can I help you?” when the owner called, I was hired to be their bookkeeper. As I mentioned previously, I had no business or accounting training, but I did have an affinity for math, so the folks leading this company fired a sweet older gentleman named Ernie and replaced him with me.
There I learned: If you have an aptitude, you can learn on the job despite not having the credentials on paper. But you need your employer to see your talents. I also learned first, running your home bathroom renovation through your business bank accounts is frowned upon by accountants, and second, when you’re old, no matter how long you’ve worked for a company, they’ll fire you in order to bring in someone younger who makes less money. Remember, even if the bosses are nice, they’re not your friends. It’s business, yo.
5. When I couldn’t take that Staten Island contractor vibe any longer, I moved on to my next gig as the front-of-house manager at a barbeque restaurant in the city. You may be sensing a theme here: I was once again not qualified for this position, but I knew a guy who knew a guy, and I got the job. Less than a year after donning my apron, there was a fire, and the restaurant burned down. Yes, it happened after I closed up for the night, but I suspect the fire had more to do with their lack of profits than my closing up shop.
Things I learned there: Managing people is hard. You want people to like you, but you can’t be their friend. Sometimes you have to fire them or tell them they need to wear deodorant, which is not fun. Oh, and it’s always good to know someone. Connections beat an unsolicited application any day.
6. Post-fire, I was back at the temp agency. They placed me at Citibank on a long-term temp assignment. Then some lady quit, probably from boredom, and I was hired as their latest Mortgage Delinquency Specialist. To this day, I don't know what I did at that job. The quitter trained me by taking her giant desk blotter calendar and saying, “Each month, tear this off and write these tasks on the calendar for next month. Then do them, and you’ll be fine.”
Things I learned there: Sometimes you don’t even have to know what you’re doing to be employed, and if you spread out a lot of folders on your desk and say, “Woo. I’d love to help you with that pool loan report, but I’m swamped,” people will leave you alone. I also learned that coworkers and bosses will form opinions about you based on what you wear. It may not be fair, but it’s true. This job was in the mid-90s, and I never met a vest that I didn’t immediately put over some silky button-down. I called it business casual; they called it sloppy. One day, upon arriving at work, a coworker yelled out, “Hey, Robin. Who ironed your clothes? Stevie Wonder?” They gave me a denim vest at my going away party and said, “Don’t you just love it? We all agreed it was so you.” It was from Levi and was not, in fact, me. So, consider your wardrobe when you head into the office.
7. I donated my denim vest and moved onto the internal temp pool at MTV Networks. A stand-up comedy friend told me that if you could get into that temp pool, you’d work like crazy and get to wear shorts. “Where do I sign up?” I thought. I called the temp pool guy once a week (from my Citibank job while not working) until he brought me in for an interview. That temp gig led to my permanent gig as an assistant to the best boss I ever had. I thought I was going to work for him while I finished my acting program, then quit as soon as I got famous. I figured it should take a year, two max. Nineteen years later, I followed him to my next job…
There, I learned that Persistence matters and that sitting next to great leaders makes you a great leader. You naturally pick up the management style of those you work under, so choose wisely. Also, empowering people beneath you doesn’t make them a threat to your success. Instead, it lifts the entire team up. I can’t leave out that I learned the importance of signing up for the 401K. I missed three years of investing in my retirement accounts because I was sure I was about to be plucked from obscurity for my very own sitcom. Still waiting on that, Universe.
8. I followed that fabulous boss to a glitzy tech media company. We were bordering on co-dependence at this point, but when you get a good thing with good people, you go with it, right? Well, maybe. Maybe not. I realized I had locked myself in golden handcuffs, taking the money, taking the great boss, but perhaps not hustling quite as hard as I could have for my acting and writing career. The company was a hot mess, but also my safety blanket. Then, my boss/friend left me there, and suddenly, I was forced to reinvent myself. Luckily, I stepped into my role as a podcast producer. After six bosses and 7000 new initiatives (none of which we finished), I decided to leave corporate life and head out on my own in order to live that glorious, tumultuous, freeing, frightening life of freelance.
There I learned: When new bosses come in, they want to put their stamp on things. They don’t want to hear all the reasons why it can’t work. They want you to be quiet and do it. I also learned there comes a time when you can’t continue to sit and say yes to ideas that you’ve tried 14 times before with the 14 previous bosses. Sometimes, you have to believe in yourself and take a leap of faith.
So here we are today. I’m working out of my bedroom. It’s not glamorous, but I’m working for myself and making a living from my creativity. Did I take a circuitous route to get here? Maybe. But maybe everything I did at every one of those crappy jobs helped me get to where I am today.
Look, friends, my quagmire of a C.V. has taught me so many skills and insights that I’m using today. First of all, no one knows what they’re doing. Even the loudest, most arrogant boss washes their hair in the shower and wonders if their big plan for the team or the company is actually going to work.
If no one knows what they are doing, why not be bold and take big swings?
Just remember that as you go along, pick up every skill you can at whatever job you’re currently at. You don’t have to replicate the micromanaging style of that boss who made you want to quit every damn day, but you can take the best of their style and leave the rest.
Move on from a job if you become the toxic one. Treat people well because someday your intern could be your boss. And whatever you want to do, figure out a way to go out and chase your dreams.
Don’t be stopped by imposter syndrome or that feeling that your resume is too light. Let that hiring manager know you’re the perfect person for that job. Say it loud and proud, as they say at my kid’s school.
You got this.
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If you’re all jazzed up and want to hear more about a person on their career journey, check out the latest episode of Well…Adjusting. Kayley, is a freelance writer and audio producer joins to dive into the struggles of creative life—from battling rejection and imposter syndrome to overcoming the fear that paralyzes action. Lauren LoGrasso, host of Unleash Your Inner Creative, joins as our Expert of the Day to weigh in on how to build structure, find confidence, and give yourself grace as you navigate the artistic hustle.
We’re all in this together folks! Get that dream job.