Procrastinator perfectionism & Optimism as a double-edged sword
My belated reflections on product management 6 months into my first rotation

It’s been a while since we last talked! I’ve procrastinated on writing this for various reasons (see learning #3 for the main reason). But I’m learning to go against my perfectionist tendencies and just get my imperfect thoughts out there.
So here goes it: nuggets from my first six months in a rotational product management program. Delivered straight to your internet door. 📩
What goes up must come down
You know those first two weeks of freshman year in college when it feels like someone just hit the refresh button on life? It’s a new chapter, and suddenly we have the freedom to write whatever story we’d like. You mean, I can have ice cream for dinner? Indeed. Life is good.
But then: the not-so-fun parts of college begin to creep in—the midterms stress, the homesickness, the loneliness, the club rejections—all chiseling away at your idealistic image of what college is supposed to be like.
Enter the same story, aged a little with a wrinkle here and there.
Six months in put me just past the honeymoon stage of early grad PM life. Alas, the shininess of the program’s promises has worn off leaving me to face off with the reality of being a young new grad in a large tech company.
It went a little like this:
From I’m going to learn fast, move quick! → To I’m blocked. I don’t have access to XYZ team’s dependent data. Guess I’ll have to wait for Sally to get back from vacation.
From I’m going to solve problems X, Y, and Z → To I’m just going to solve X. Y isn’t prioritized by leadership to be resourced. We don’t have the right technology in place to solve Z.
From I’m going to develop and apply all my technical design & data analysis skills → To I’m going to develop my stakeholder management, triad partner collaboration, and communication skills.
Most tragic one yet, from New grad? Attend this development workshop and receive a free Uber Eats voucher! → To You’re on your own! Get your own food. Gone are the golden days.
It’s a classic coming-of-age tale. Girl starts work with an abundance of optimism and naivete. Girl struggles with various obstacles to ship a feature. Girl must come to terms with the limitations and characteristics of big organization and limitations: bureaucracy, politics, and dependencies that can hamper velocity and autonomy. But in the process, girl becomes woman. A working woman, I might add. Aheh.
What goes up, must come down. Innocence lost, but wisdom found.
Get comfortable with the “yes, and’s”
Surpise, plans change! Your team becomes understaffed after a staff engineer moves teams, an unexpected dependency is discovered setting back the timeline, and you’re asked to share aloud thoughts on a strategy or design you’ve never seen before on the spot.
As a fastidious planner, I would be aghast if I wasn’t given the heads up for these things — I need to plan for it! I’d exclaim.
But product management is a continuously running five-act play of improvisation. It involves taking what you’re given and running with it time and time again.
I’m learning to get better at this skill. Curveballs are expected and normal so best to plan for them by keeping flexibility in mind and brandishing the courage to march forward even when things don’t go to plan.
Procrastinator perfectionism (my worst enemy)
I‘m gonna put this off until I have the right information to get started.
I’ll hold off on committing until I feel more confident it’s the right decision for me.
Famous last words.
I tend to wait for the perfect conditions before I start anything. But in doing so, I hold myself back because the perfect conditions tend never to arise.
When these feelings surface, I try to step back and remind myself that now is a good time to start. Perfect won’t happen right away. In fact, it may never happen. But that shouldn’t hold you or anyone back from striving towards something that’s still really great. Almost always, something is better than nothing.
Re-defining self-worth
From the moment I entered the workforce, I began tying my worth to that defined by the corporate world. If I didn’t perform well against the PM competencies, I felt inferior like I didn’t belong in this role at this company on this team. In retrospect, this sounds silly.
For starters, Growth Mindset ™! Anyone and everyone can improve with time and deliberate effort. It’s good to be self-aware about where there’s room to grow.
But most importantly, your self-worth should not, I repeat, should not, be calculated by measures of capitalist productivity. Life is much grander than work. Remember that you play many roles beyond an employee or a coworker. How would you calculate your self-worth if being a good friend/daughter/son/plant mother/cat father/home cook/part-time student/etc. was the judging criteria?
You are doing the best you can given your circumstances that only you have visibility on.
Optimism as a double-edged sword
In many situations, optimism is great to have. When you’re optimistic, you tend to persevere.
I’m often told that I’m quite an optimistic person. I cherish my optimism more than I deplore it. However, every quality becomes a weakness when taken to an extreme. At its extreme, optimism means seeing everything as an “opportunity to learn” and taking on additional work that I probably otherwise shouldn’t. Other times, it means not being critical enough to question the viability of an approach since I’m optimistic what we have will work.
Over-optimism leads to an overestimation of the benefits and an underestimation of the costs.
I’m practicing pausing, debating with myself, and pushing back more often. When it comes to countering the opportunity to learn, I think about being intentional about the work I take on and correspondingly setting up the right boundaries to protect my time to do what’s best for my growth. When it comes to plans and ideas, I’m trying to get better at playing devil’s advocate to help the team arrive at the best and most accurate solution.
Being more assertive
When I started the role, most of what I worked on was drawn out for me. My projects had already been scoped and my training sessions were pre-selected. I was essentially working off a script written with my name on it.
A little bit of passivity is normal when you first start a new job at a new company. After the first few months of onboarding though, you’re expected to take the reins of your job and write the stories that will give your career your happy ending.
If you want a fulfilling rotation (and career!), be assertive. Identify what you want to do and make it happen.
The PM Diaries is a new outlet of mine to document my career journey. But secretly, it’s a forcing mechanism to surrender my thoughts to pixels & paper and produce something I could call my own, all at a sunk cost of $5/month. Here’s hoping that $5 stretches further for you than it does for me.☺
~ Kaci