The Legs of My Stool Are Wobbly

A few years into my career, a good friend suggested I make a “Praise” folder in my work inbox where I could collect nice things bosses, colleagues, and clients said about me. These weren’t necessarily extravagant compliments, but a thoughtful comment above your basic “thank you” qualified. I collected items with some regularity. While I didn’t refer to the folder often, I reviewed it when I needed a boost of confidence or a reminder that I was doing good work and was respected by my peers. So when I started a new job 18 months ago, I dutifully created my new “Praise” folder. Then I waited. Over a year into my new job, the praise folder’s contents are scant — and I could use its support more than ever.


I’m in the solid middle stretch of my career. After 15 years of employment, I’m now working at a company widely recognized as a market leader, in a position people might consider enviable, yet in some important ways I have never felt more unsure of myself. At a time in my life when I assumed I’d feel settled and certain about my abilities, I have been doubting my skills and intuition like I am just out of college. My work sense of self is a stool built on expertise, praise, and culture, and right now all of its legs are wobbly.


In former jobs, I got to bring a lot of my creative self to work — and a good idea could go from mere thought to approval to implementation in a very short amount of time. I worked at businesses that basically flew under the radar of industry news; direction and scope could be changed and mistakes were easily corrected without a press release or public fuss. In my current job I have influence but little control, and my creative self is much more constrained in part because of my role and in part because of the ungainly amount of work it takes to execute almost any idea, no matter how small. Everything requires buy-in from multiple teams, to say nothing of the legal considerations and optics due to the scrutiny that comes with being a public company. Minor mistakes can become headline news. It doesn’t feel like a safe space to experiment and fail, and the lack of opportunity to get things wrong means my risk muscle has shrunk and destabilized my sense of my own judgment.

I’ve always loved being praised and feeling like I’m ticking things off my list (sometimes to a fault). The part of me that relishes affirmation and relies — maybe too much — on external motivations misses the forward momentum that this fuels. I spent the vast majority of my career working a boss who praised me early and often; we had an easy rapport and I drank up his approval. My new boss is kind but significantly more restrained with his feedback in a way that makes it hard for me to differentiate between what is explained by his style versus my performance. I’ve had to learn to survive on less praise and rely on my inner sense of motivation and sense that I’ve done something well. (Admittedly some weeks this is easier than others. I’ve also taken to doling out compliments very liberally in the hopes of creating a more praise-friendly culture).

Culturally, I’m more at sea than I’ve ever been. I’ve always worked at small businesses — mostly very small business of fewer than 25 people. It took some time to learn the ropes of these jobs, but they were small machines and before too long I could discern what was required of me and become competent in core areas. This was great for basic comfort and allowed me to get more ambitious in my larger thinking and projects. In one of my most recent positions I was responsible for managing the voice and identity of an entire business. The challenge was exhausting and thrilling.

My new workplace, however, is a giant, tens-of-thousands of people machine with layers upon layers of teams, identities, products, countries, priorities, disclosures, and responsibilities. It is more like a city than a traditional business in its complexity. My piece of it is small and narrow, and a “stay in your lane” culture means it isn’t easy to learn through involvement in other team’s projects. Nor is there a strong sense of being on a single team with a shared purpose, of pulling together in the same boat. It’s acknowledged to be an environment without a strong culture of mentorship. My role, and the roles of many other employees, is classified as “independent contributor,” and this is as much a feeling and a state of mind as it is an HR classification.


It might sound strange to say given all of the above, but overall I actually like what I’m doing in the day to day quite a lot, and I’m really happy to be in my industry. I love working with other creators, which in many ways is the core of my role. At some abstract level, I’m even grateful for the opportunity to learn how an organization like this functions, but I’m struggling with how long and steep the learning curve seems to be. Ironically, the last time I had the trifecta of expertise-praise-culture in the workplace was also when I was feeling stuck, stiff, and a bit bored. Confidence and security, which I find myself yearning for today, can so easily transform into ruts.

I happened to start my new job shortly before coming a parent, and kids have a way of intensifying and clarifying experiences. My job now matters both more and less than it ever has — more because of money and stability, more because I need it to remember my identity outside of being a mother, more because I want to model a certain kind of relationship with work for my daughter (a topic for another post, no doubt). And less for all the obvious reasons, primarily that nothing matters as much as my family, not even close. While being a parent hasn’t directly contributed to a less stable work self stool, it has made the wobbliness more intense.

Even though I know better, there is a part of me that assumed my career would be a simple upward trajectory. The last couple of years have reminded me that most careers — and certainly careers that involve any amount of risk — have ups and downs, zigs and zags, restarts, and unexpected changes. A year and a half into this position, the legs of my work stool are beginning to feel more stable in some areas, although I’m not sure I’ll ever develop the sense of confidence in this role that I’ve had in others. In the meantime I’ve gotten more comfortable speaking frankly about my frustrations to colleagues, and I’ve found that I am far from alone in my feelings. This has been hugely validating and has taken my concerns outside the realm of the personal, where they’d been hovering as I questioned what my problem was and why I didn’t feel a greater sense of confidence and direction.

One benefit of being an independent contributor is that I’ve been able to largely set my own priorities. Once I got comfortable with the basics of my job, I found the sense of self-direction exciting and fun. There is something freeing about the ability to set your own agenda and handle all the big decisions even if your fiefdom has a population of one. While I don’t receive heaps of feedback from colleagues, I have heard lots of nice feedback for the creators I work with. I’ve always liked enabling people to be more successful at what they’re already doing, no matter what job I have, and in this one I find  a sense of pride and purpose in being a friendly, responsive, and helpful human who can help outsiders navigate the machine more easily.

I’ve also concluded that while the culture of this company has evolved for legitimate reasons, that doesn’t mean it serves us in every area — and one where I think we’ve lost out is emotional intelligence. Public scrutiny and a complicated team structures may make decision-making slow and arduous, but we can still bring more humanity to our communication, priorities, and spirit.

My new approach to work satisfaction is to bring as much of my own personal culture and values to my work and my professional relationships as possible. I’m trying make adopt a tone of lightness and play in meetings (which tend to be all business) and a more informal, direct tone to interpersonal conversations (rather than worrying about being wrong or not having all the information — which is practically unavoidable). I now have four unsolicited emails in my Praise folder. I’m glad to have them, but I’m trying not to hold my breath for more.


Image: Louise Bourgeois, Arch of Hysteria (1993)