When “Near Wins” Feel Like No Wins

Well, long time no see. The past six months have been the hardest in my life. And while my insane hours and financial stress and physical exhaustion obviously have a huge part to play in that statement, the root of my struggle is a lot deeper than those surface triggers. It turns out, I’m not good at something and it’s really hard to stomach.

To provide some context, I’ll get on my high horse really quickly and explain that I am extremely goal-oriented. I thrive on receiving a challenge and crossing it off my to-do list in record time. Senior year, I took a chance and accepted my current job even though it wasn’t exactly what I had envisioned for myself- but it provided a foundational experience I would need to succeed in my future plans to advocate for educator and students. Even when running on fumes the first few weeks into training, I was mobilized by the excitement of receiving challenges and solving them as soon as I could. After all, up to that point I had never been hung up on ‘mastering’ something for very long. Well, if you ever want a check on your ego, take a high-stakes job that spells the words urgency and feedback with all caps.

At my current school, we have established a “near win” culture in which we can celebrate the near win but must thrive on always finding a component upon which to improve. Brilliant in theory and a great way to push performance from good to great. But, damn, it sure is hard to get used to. When I was first receiving feedback, I felt like I had been metaphorically reduced to a broken cog, doing nothing but disabling the wheel. I thought, “if I’m so bad at this, I need to go. I need to go do something I’m good at. It’s not fair to the stakeholders in this. They don’t have time to wait for me to get better and I don’t have the stamina to make all these gains this quickly.” I felt targeted and worthless. It didn’t feel like “near wins”- I wasn’t winning anything at all.

Fast forward a bit and I’ve grown- if not in strides towards mastery of my craft then at least in strides towards my mastery of openness. I’ve come to understand that the feedback comes from a place of caring and investment; my supervisor and my boss are invested in my success because they are invested in the success of the school as a whole. It took what felt like every ounce of my pride but I have arrived at a place of balance with my work life. I am far from a finished product, but in the re-birth of this blog as a resource for others, I wanted to impart some of the wisdom I have gathered during my “baptism by fire”.

  • Practice a 24-hour rule: when something disappointing/frustrating/hurtful happens in any aspect of your life, take 24 hours to emotionally process it. That includes the poker-face-still-at-work stage, the hysterically-crying-into-your-steering-wheel stage, the fury-driven-i’ll-show-them stage, etc.
  • Keep the venting off premises: And I extend this to mean, talk about your feelings to people that do not share your work environment. Everyone rejoices in shared struggle, but complaining or venting to co-workers, even when they may agree with you, only brings down the morale of the room. Everyone has stress at work, so drive home, pour a glass of wine, and let your best friend hear about it over Skype.
  • Articulate your concerns to a mentor first: There are cases where you are right to feel frustrated and sometimes those cases are affecting your performance to the point that you need to speak to your superior about it. The most helpful thing I have done this year is to practice articulating my concerns to someone who knows how the world turns. My mother is a self-made business aficionado and after she has listened to me shed a tear or 200, she will tell me what I should change in the way I professionally deliver my thoughts. I have felt so confident and calm going into hard conversations at work because I was able to articulate my concerns to highlight my frustrations without pointing the finger or coming off ill-aligned with the company’s values.



As twentyeverything’s, we have so much more to learn and that path will not always be paved. Let’s face it: we aren’t always good at this…..yet.

– Jess


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