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That Time You Hustled Like the Boss You Are--The power we let slip through our fingers



Twenty years ago, I was a waitress -- a title I didn’t exactly put out there for common knowledge. I was a decent waitress and satisfied that my performance almost always led to an average of at least 20 percent gratuity. I made a lot of money back then in a fine dining steakhouse. Some weekends I was able to pay my rent from just one night of tips. I was young with deep pockets for someone so young, and completely unaware of the growing power I possessed with each tip I earned.

At that restaurant, I worked alongside a team of some of the most hilarious characters I’ve ever known. Some shifts were so nutty that I can honestly say I have never worked with such camaraderie since. There’s good reason for that. The staff was comprised almost entirely of actors, dancers, and musicians, who, like me, pounded the pavement by day and dished out steaks at night. Maybe a few team members were professional servers, staples to the mechanisms of the restaurant, dedicated to a career of guaranteeing memorable dining experiences. The rest of us showed up for cash and, I suppose, for the company of like-minded coworkers too.

The steakhouse was across the street from the Winter Garden Theatre and brought in a slew of tourists. As Manhattan servers, we were often asked by small town guests (eager to take home a bite of the Big Apple) why we moved to New York. We would naturally respond with whatever career for which we came. Guests were often amazed. I guess they didn’t meet a lot of actors, dancers, and musicians in their towns. We were like aliens to them, strange creatures who looked normal but lived fantastic double lives, waitresses by night, dream hustlers by day.

That’s exactly what I was doing there -- living a double life. I worked my job and left it there at the end of the shift. I didn’t wear my waitress persona elsewhere, out where I was testing the credibility of my talents. Yet 80 percent of my income was earned through the tips of those tourists. And still, I never once called myself a waitress. That was just a job, never a career. The career was worth proclaiming to the entire world, even though in dollars it was worth almost nothing.

And I wonder now how more valuable I could be to myself today if I had just admitted then that I was a waitress?

There are two commonly argued opinions about how we view the circumstances in which we live. One is the belief that life happens by chance -- a series of events that occur without any meaning. And the other is the belief that nothing happens by chance -- everything is intentional. And while I find the idea of relying solely on chance to be rather depressing, I also don’t think everything merits a search for deeper meaning. Thus, I surmise that humans are too complex a model to be painted with such broad brush strokes. And what’s more, the world in which we live is equally complex. Yet we consistently box one another and ourselves into ideas, theories, and titles. Meanwhile, we’re a most extraordinary mix of colors and mediums, as complicated as the most abstract painting.

We needn’t look far for proof.

For all the pitfalls of social media, there is a definite upside. It’s easier than ever to have an idea and crack the right algorithms to get that idea in front of an audience. Hop onto any platform and you’ll find numerous influencers, bloggers, entrepreneurs, and thought leaders churning out content on the daily. It’s the age of the hustle like never before, except that the hustle we see is almost always a selected image extracted from a bigger, more complex person at work. Behind the pages we follow are legal secretaries, fourth grade science teachers, and sales reps. There are also quite certainly substitute teachers, consultants, and yes, waitresses on the flipside of your favorite influencer. To every hustle there is likely a side hustle, and sometimes that side hustle is the only way the hustle you see even happens. Few discuss how their magic actually takes shape because with each post, picture, video, and blog, the accounts you follow are fitting themselves into the box in which they think the light will shine upon them brightest.

I know because I do it to you. And how foolish am I to think it wise to discredit the work that allows me to do what I love.

My passion for language and written words is satisfied and made possible -- at the moment-- by hustles and gigs. The writer behind this blog is a marketing consultant by day. I do that work each day and then return here to give this hustle the regard and belief all dreams need. And to ignore what allows me to do that is to suggest that dreams and the careers born from them happen out of thin air -- like chance. We’re far too complex for such happenstance. So maybe the better brush stroke paints a deeper possibility: if we view chance as more than chance, but also opportunity, what we strive for just might come together with a greater impact.

Starting with an opportune chance we take on our audience.

One account I follow is a well lauded performer. She has appeared in numerous musicals, concerts, and cabarets to the delight of a loyal fanbase. Beyond her life onstage, though, she’s a music teacher and choir director, a full-time hustle she’s had in addition to her performing hustle for more than 13 years. Yet up until this December, she hesitated to showcase her job in the same way she shares her professional performances. What if it wasn’t up to snuff, compared to the work for which she’s known? But she finally mustered up the nerve and took a chance, inviting all her followers for the first time to see her student choir’s holiday concert.

I was present and heard several numbers of intricate choral work -- songs that sounded so polished they could have stood beside that of university choirs. But there were also two numbers in which her singers choked. I couldn’t help but think about her Facebook post. Would she ever be so forthcoming again? But to my surprise, when I looked around the audience, there was no awkwardness. Everyone was on the edge of their seats, waiting to see if these young musicians could push through. When they did, it was to the greatest applause of the night. That night I witnessed beautiful, complicated measures of music that marked the potential of a strong choir, but it was the complexity of human nature -- an audience rooting for singers who hadn’t yet made it -- that I took home from that concert. We love success. But more than anything, we love a good success story. Just as it’s foolish to discredit the work that goes into making our dreams possible, it’s foolish to discredit the best of human spirit, that part in each of us that celebrates the process people go through -- performers, athletes, business leaders, and of course, dream followers who wait tables -- to make dreams reality.

Back in the day, the title I preferred to shout from the skyscrapers was a title with very short legs to stand upon. Yet I wanted it badly enough, so I put it out there anyway. I suppose I believed in myself. But I didn’t honor the dream enough to acknowledge that nothing comes without work, especially the hustle and grind that separates dream followers from dream makers. In my inexperience, I never stopped to consider the greater success I could find if I embraced the freedom that comes from work. Would I have pounded the pavement harder had I been proud of the work that made it possible for me to hit the ground running? Would I be farther in my career if I embraced how good it feels to truly earn something? Where would I be today, if twenty years ago I valued myself enough to take the opportune chance of not giving a damn about how others would perceive me? What if I gave a damn instead about how I could inspire others to work for what they believed possible?

I know enough to know there is no shame in the process of becoming you. There is no shame in honest work. There is no shame in putting food on the table, contributing to society, and doing whatever is necessary to not settle for the life we do not want. Earning an income isn’t cheating on dreams. If anything, it grants dreams. Grit, dedication, and the will to push through the most mundane tasks isn’t unique to waiting tables or filing papers. For every dazzling aspect of our most wished for goals, there are a handful of dull orders to make those goals happen. And just as an audience’s gut reaction is to root loudest for the singers who choked, so too is the spirit of those rooting for you and me.

Who cares about titles and images? Imagine the followers and fanfare in store for us when we admit just how much we’re doing to get what we want.

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Dec 19, 2019

good one, you hustler, you!


Annie D. Stutley

the short story

Back in 2017, “That Time You” took its first steps—a blog that humorously and inspiringly chronicled the chaos of everyday life. It was a canvas for what I referred to as “gaffes with glory” (what others may call hot mess success tales) and also resolutions for how to tackle seemingly insurmountable challenges, plus personal victories within the daily hustle. I've never had all the answers, and truth be told, I still don't. Yet, I spoke the language of the Hot Mess and Walking Disaster, understanding that we don't need to have it all figured out or succeed at everything to truly grasp our purpose.

However, 2021 brought a drastic turn: I faced a Stage 3 cancer diagnosis and tragically lost my mother during my sixth round of chemotherapy. My path forward seemed impossible. Stumbling took on a whole new weight—it became a burden I struggled to carry in a place where trust felt elusive. “That Time You” evolved at that point because I evolved. Stripped of my plans and the future I had envisioned, I found solace in my one constant: my faith.

Since surviving cancer (and the loss of a parent for the second time in a two-year period), I transitioned into a full-time editing role and also poured my energy into contributing monthly to three different magazines. “That Time You” was put on a purposeful pause—two years for recovery, rediscovery, and revision. I'm gearing up for a relaunch. This time around, whatever I share with you will be rooted in the wealth of experiences I’ve gained over the past three years, because sometimes stumbling becomes an essential part of our path, forcing us to dust off our fuzzy socks and bravely venture forward, wiser.

“That Time You” lives on, on this site, and I do promise to continue to share my misadventures with meaning and celebrate blunders alongside triumphs. Yet, I’ll be chronicling the certain enlightenment amidst life's darkness—a testament to faith and, hopefully, a guide for uncovering God's presence in every situation, whether it's the mundane or the profoundly challenging.


Thank you for being a part of this journey.

Much love,


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