Mile Markers: The Successes We Don’t Always See Coming


Mile Markers: The Successes We Don’t Always See Coming

We all set career goals for ourselves – and once we actualize them, success is foreseeable. At first it sits on the horizon, but with time and effort, it gets close enough to reach out and touch. We prep for that goal and put in work, progressing along on the path as we pave it (probably hitting some potholes along the way).

Reaching a set goal is a huge moment for us. We look forward to it (and back on it) with intensity and pride. That moment is a roadside rest stop interrupting a tiring, tedious stretch of freeway. We start seeing signs for it miles out. We prepare for the moment when we pull in, put it in park, and probably overpay for a Whopper Jr. before motoring on towards our next goal.

It’s that sense of achieving something that wasn’t even
on our radar.


We all talk about this kind of success a lot. And it’s important to, because setting, reaching, and receiving support for major goals is critical to professional growth. 

But there’s another kind of success we experience, and it’s worth talking about, too. It’s that sense of achieving something that wasn’t even on our radar. Life throws opportunities and experiences at us in a flash – sometimes we process them so fast that we don’t see how pivotal, memorable, and formative those moments are until they’re in the rearview mirror. 

Let’s call these moments “mile markers”. 

I work at SpotHero, where we have women representing creativity, innovation, and leadership on every team. As their colleague (and in many cases, I’m happy to say, friend), I could easily fill you in on their big successes: projects completed, promotions earned, opportunities created, and awards won.

But as I was thinking through the story I hoped to tell in this article, I realized that while I was aware of these women’s’ monumental accomplishments, the ones that got them recognition, I didn’t know as much about their hidden pivotal ones: the little make-it-or-break-it moments when they changed course, shifted gears, or just put pedal to the metal and hoped for the best. 

I didn’t know anything about their mile markers.

As it turns out, they didn’t always know about their mile markers either. Or rather, they remembered these moments but didn’t quite register them as successes. These were simply times when they had to choose a path or shift their thinking. While talking about these instances of decisiveness and agility and initiative, many of my colleagues had lightbulbs go off, realizing that mile markers are major successes in their own right.

Here are some of my Women in Parking colleagues’ mile-marking stories.

Nicole Wylie’s mile marker was a mind shift. Early on at SpotHero, her charge was breaking ground in new markets and verticals, and she grew accustomed to being fluid, acting intrepidly, and rolling with the punches. But her back-to-back promotions to Director of Sales and then General Manager planted her in a highly visible role in our hometown of Chicago. These promotions were publicized accomplishments, but the mile marker behind the scenes was Nicole’s conscious pivot of her working style and ideas about what success looks like. She shifted from scrappy to strategic. It’s this mile marker for Nicole that created an environment for hitting big visible goals like growing strategic relationships, building a killer team, and joining the 2018 board of Women in Parking.

Michelle Jackson, as an early employee, had to take initiative as we blossomed from a handful of enthusiastic kickstarters to a larger workforce. Through her experience as a customer service representative, she started seeing connections between the issues she solved for parkers and the proactive support we should provide for parking partners. Michelle’s mile marker was overcoming a personal struggle before joining the sales team as an account executive: uncertainty, for the first time, felt a bit scary. She convinced herself she was ready to learn a new skill set, and thanks to this mind shift, she was able to take her career to the next level.

Every startup has it’s “wild west” period. Hallie Kolsen was one its pioneers. She kicked off her career by supporting sales operationally, but her interest was piqued by client-facing responsibilities. One of Hallie’s concrete goals in her role as account executive was to launch a new market, so she set to work and soon jetted off on her first client visit – where she closed her first big account. Hallie’s mile marker was realizing that she, a young woman early on in her career, already had the foundation for sales success due to an inborn ability to build authentic relationships. She realized she could use her intuition during the sales process, and by so doing, she launched twelve new markets and has succeeded in a series of new roles ever since.

Through incessant advocacy, both personally and from her managers, Bridget Boylan recently carved out a brand-new role on our sales team where she contributes unique value. Her mile marker was learning that self-advocacy isn’t entitlement or boastfulness – rather, it’s helping your internal champions understand your value and how you plan to contribute more of it. She compiled a “brag book” and communicated how she was qualified to meet a clear need. Today, she’s our first ever account manager.

As for me, well, 18 months into my parking career, I feel like I’m getting my footing. Those of us who have been in the workforce for a while know that it’s thrilling and humbling to learn a new industry’s in-and-outs. I’m proud to say that I’ve been able to hit some big goals – and experience many mile markers – while starting and scaling a program I believe in.

One thing that my colleagues and I are united on is that we feel that Women in Parking has helped propel us towards our goals. This community grows confidence, expands perspectives, and facilitates learning and advancement. And one thing we do really well, fellow WIP members, is celebrate successes: both the big achievements and all the unspoken ones in between.

SARAH BECHERER is Sr. B2B Marketing Manager at SpotHero. She can be reached at


Article contributed by:
Sarah Becherer
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