A Good Boss Tells You When to Rest

This is a repost from a LinkedIn article I wrote in 2020. Photos are stock photos.

I am a Type-A, eldest child, only daughter, former USAF Officer, workaholic working as the most junior and as the only female developer on my team. Any way you dice my personality and circumstance, all signs point to a driven employee with something to prove and a chip on their shoulder, a desire for organization and proper leadership, and a tendency to have their self-worth intertwined with performance and productivity (don’t worry, readers-- I’m in therapy, it’s being handled... sort of). 

At home, I single-handedly got us the best house for our budget, and set-up a monthly budget so that we paid off $120k in debt (student and otherwise) in 2.5 years. At my job in Capitalist America, I elbowed my way into not only front-end code development, but also designing our team’s mock ups in Figma. I get such a high off solving problems and accomplishing challenging obstacles, that I don’t remember the blood, sweat and tears that came along the way. 

It’s a self-perpetuating cycle: new problem, work hard until resolution, experience dopamine release, confidence to tackle new problem, problem, repeat. I’ve gotten a lot better at asking for help, and I’ve gotten better at saying no. Because it’s never about pleasing any boss or being liked by others. It’s that I can’t stand the idea of me not knowing or not being able to do something. So if asking for help or saying no ahead of time saves me from feeling like I let myself down, then I’d rather nip any sense of discomfort earlier than later. That sense of self-protection extends to those around me-- growing up, I was the defensive and stoic guardian of one of my brothers, a person with Autism; and now as an adult, I swing between ensuring my diabetic husband’s health needs are met, and that my incredible team at work is confident that what I’m assigned, I’ll solve, because they work too hard to have any one person not pull their weight. Which brings me to why on earth this entire diatribe was even considered LinkedIn-worthy: ‘good bosses tell you when to rest’.Our team had a new project, and I was assigned to take the crude, rectangles-everywhere, whiteboard wireframe from my product manager, Phil, and mock up the true design in Figma. I balanced designing that assignment and front-end coding for another feature, and after about 14 consecutive days of long days straddling two worlds, my design had been nit-picked and approved, and my code branch for the other feature was merged. The mock-up looked like a colored, detailed clone of the crude wireframe my product manager assigned me. I met every requirement, the design matched his vision, and it utilized our component library and would be simple to implement. The team was happy with my creation, and we were ready to move forward into development. 

But I was haunted: I despised what I designed, and I was exhausted from using both my ‘code brain’ and my ‘design brain’ on full engine blast in the short period. Everyone was satisfied and I was mentally fatigued, I had the right of way to wrap up and move on to the next assignment.

So if I checked all the boxes and received approval, why did I turn to my team lead to express disappointment in my work? Why couldn’t I just take the win and move on? And the group who went through the design process was tired, too. We wanted the next thing. 

Because though I had drafted several iterations and nit-picked my designs ad infinitum, the design wasn’t good enough for me, and if I’m not proud to put my name on it, I didn’t want my developer peers to put their name on the product, either-- they deserve better. Furthermore, I had just designed the mock and executed the code for that mock for another feature. The excitement around the design and feel of that product was palpable. A product received with enthusiasm compared to a product received with a nod of approval feels different, especially when I shared the sentiment.

I went to Craig, my Superman Supervisor and Guru of Guidance in All Things Software, and I leveled with him:

‘Craig, man, I hate my design. I was so locked into meeting what was desired, that I didn’t consider anything beyond it. I’m not proud of this. I know we green-lighted it, but I’m not walking away feeling good about what I’ve done. It feels like our dev team has the skill set of a Ferrari, but my design is that of a Camry.’

Suspensefully, I watched Slack show that he was typing, and then pause when he stopped, and then appear when he continued. I assumed that he had a lot on his plate, and he would say something to assuage my disappointment and encourage me to try better next time so that we could tackle the rest of the project board. But alas: 

“Approach it from another angle. Take a break. Go for a drive. Step away and do what you need to do. You’re in-between assignments now so this is the time to do it. But rest and walk away.

You can accept what has been done and we’ll be fine. Or, maybe do a mock up ignoring everyone. Just make something using your own constraints and see if the inspiration hits. If we end up with some boring scrolling box, so be it, but at least you have something in the mock that we can point to and say that's the real solution, why can't we get there? There really isn't much room for free thinking in [this basic utilitarian feature], BUT I think just accepting that fate is probably wrong, and we'd be doing ourselves a disservice if we didn't go "how about....this?” If it gets rejected, it gets rejected, but at least there's a version we are proud of even if it's not implemented.”I sat with his response, in a bit of disbelief. I had been grinding long hours everyday for a while, I knew how many to-do’s we had on our project board, I knew that any more time on this particular part of the project flow was going to force Craig to act as a shield for me when someone above his pay grade started asking questions about timelines and deadlines. I knew that any new mock-up I created was going to force the team to do another round of nit-picking and approvals. Craig knew all of this, too. But he believed in me, we had an approved back-up, and if the quality of what I rogue-created was to be such an improvement, it would be worth the wait.I thanked him for the opportunity, and I shut my laptop at 2pm on a Wednesday.

I hopped in the SUV and made a beeline for the local foothills of the Rockies and played my music and watched deer and birds and I didn’t think about anything related to that d*mn mock-up or the pressure of the corporate hierarchy or anything having anything to do with work. I grabbed coffee at a mountain cafe, I watched trout rise in the mountain-fed rivers. I came home, ate dinner, and hung out. As I headed to bed and thought about how I’d take a crack at the new design in the morning, inspiration came in gale force. I scrambled to my laptop, threw on my blue-light glasses, and cranked out my own interpretation of what my product manager wanted. Not only was the new mock up significantly better than what I mocked up prior, but in the surge of inspiration-fueled energy, I learned new tricks and tools for Figma, elevating my ability to design future mock-ups with increased improvements. Phil was up late, too. I could see his mouse move around on the Figma board, starting with the previously approved design and over to my ‘go for it’ design. My heart sank a bit. I waited on his Slack message to tell me to stop, that we had an agreed design, to just move forward. I saw notifications light up on Figma. There were three comments from Phil on the new design -- two that nit-picked certain details, and the final comment: ‘This is the one’.The following morning, Phil messaged the group about the new design. It was quickly approved, with a short discussion about various spacing and pixels. Everyone was much more receptive, much happier, and had a greater sense of pride towards this new design and its future place in our product line.

While in the Air Force, I received countless hours in both leadership and followership training. There are hundreds of thousands of texts about leadership and design and software development out there. And with the post-pandemic remote-or-office debate, there seems to be even more texts out there about company productivity, communication, and outcomes.When Omnilert hired me, they trusted that I could produce high-quality results with a desirable work ethic, and do so remotely.

When I accepted Omnilert’s offer, I trusted they’d be the culture I had come to know during their hiring process. A smaller company with room to grow and roles to tackle, a close-knit team that inspired one another by nature of its small size yet great talent, and a manager that didn’t just manage but mentored, who gave space for his devs to build something, break it, and build it even stronger. A manager with a style of leadership that didn’t just dictate the standard, but led in such a way that the team rose and created an even higher standard. A manager that welcomes individual self-evaluations and is willing to extend a deadline so that the product reaches a higher quality. A manager who recognizes that hard work is necessary, but also, so is rest.  A good boss tells you when to rest.