Infatuation Passes, Love Lasts

Infatuation Passes, Love Lasts

I've been through a few companies in my career up to now. Sometimes a new job fits like a glove. You know that feeling as soon as you start. It's everything you've been wanting, everything you've been waiting for. Other times, it may not fit at all. The conversations you're a part of create a cognitive dissonance, the work isn't exciting, and you just feel like you don't belong. Then there's that funky in-between, where there's something great going on (you just know it), but it isn't all coming together like you'd want it to. All the pieces are there for it to fit, but you keep struggling to put the pieces together. It can spark frustration (why isn't this working!?), self-doubt (what do I keep getting wrong?), and sadness (I want this to work so badly...).

I recently hit my 1 year anniversary at Jane App , and in reflecting on this last year, I thought I'd have an interesting story to share. So here I am, writing to y'all about that funky, awkward, in-between.

Honey-what?

People love asking when you start a new gig "so how's the honeymoon?", usually assuming it's all butterflies and rainbows. Well this wasn't my experience at Jane. Although I quickly had a deep appreciation for every human I met (and we've got some friggin great humans at Jane ??), I had trouble wrapping my head around how to make a positive impact (and I was itching to make one). I had taken on this role as a career stretch opportunity and put a ton of pressure on myself to prove that I could do this, that I'm worthy to be here. Little did I know the number of "firsts" I'd face (or as Brené Brown would call them, FFTs ), and the stress it would create. The first time I was stepping into people leadership, the first time working for founders, the first time I had to manage the breadth of working across multiple HR functions across an entire company scope, and the first time building a People Operations (HR) function from the ground up. I had come from a previous experience that I was thriving in, with a strong team structure, a highly encouraging manager, and a very manageable scope. I was suddenly filled with self-doubt and very little structure to support my insecurities. Nope, this wasn't a honeymoon.

Reconnect to Your Purpose and Values

So a few months in, I took a moment for one of my favourite activities, journalling. I poured myself a glass of wine, grabbed a pen and paper, and put my head and heart to work. I was seeing myself move through all the roles in the drama triangle . I knew I needed to ground myself in my "why", reconnect to my purpose in joining Jane, and, most importantly, ensure my values were aligned. I've gone through an exercise similar to this in the past when the "glove didn't fit", and unfortunately my values weren't aligned, and I had made the decision to leave. This time around at Jane, they were very clearly aligned (that was a relief!). But I still had a whole list of struggles, and I didn't know how to get past them...

Choose Your Struggle

I'm a big fan of "harmony" (I'm a Type 9 Peacemaker after all). I'm constantly searching for it. I'm also consistently reminded that life's much more complicated than simply being in a state of "harmony". In the process of working through my struggles at Jane and trying desperately to make it all just go away, I was suddenly reminded of a passage a friend read me from Mark Manson's The Subtle Art of Not Giving a F*** :

If I ask you, “What do you want out of life?” and you say something like, “I want to?be happy?and have a great family and a job I like,” it’s so ubiquitous it doesn’t even mean anything.
A more interesting question—a question that perhaps you’ve never considered before—is what pain do you want in your life? What are you willing to struggle for? Because that seems to be a greater determinant of how our lives turn out.

Looking back at each of my experiences, I was reminded by the struggles I faced at every company I worked along the way. The good comes with the bad. There's no flowers without the rain. The light comes with the dark. You get it right? So if I'm going to work for a great company like Jane where we put the human part first, where we give people voice & choice, and where my values are so aligned, then I can also accept the struggles that come with stretching into a role without much structure, working with creative founders (which can be challenging and can make you better), and managing the entire breadth of a People Operations function. These are struggles I can choose to accept.

Get Out of Your Own Way

A clear theme in this story has been my struggle with self-doubt. I found that the more I thought things through, the more I'd spin into cycles of uncertainty, worry, and frustration. Clearly, "thinking it through" wasn't working for me. I knew I was getting in my own way. I thought the answer was that I just have to "change my mindset", and that belongs to me, it's no one else's responsibility. I then reminded myself of what I preach to my coaching clients, that the world moves through conversations. I realized that I was concealing my insecurities out of fear of not seeming confident, and being good enough for others. I knew that I had to reveal , to connect, take ownership, and get out of my own way. Through vulnerable conversations with my manager, my team, my peers, and trusted people in my network, I learned to calm my inner critic and get back to what I came to Jane to do - good work with good people.


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One of Jane's values is "Love Jane". I remember reading the value before starting and thinking "well that's intense, I'm supposed to just "love" the company?". Through my onboarding period and my first few months, the value wasn't sticking. I was too caught up on my insecurities. I was starting to wonder if I would ever live up to Jane's values. In the end, it was through the ups and downs, the failed honeymoon, the struggles of working through the drama triangle, that I came to love Jane.

It may not always be comfortable, the grass may look greener on the other side, the infatuation, passion, obsession we hope for might just not happen. But if I've got one piece of advice for y'all, it would be to stick with the discomfort a little longer (as long as your values are aligned). It might seem like a challenge at the start, even scary, but it's worth it when you get to the top.

Su Ganguly (She/Her)

People and Talent Lead

2 年

This was so beautifully written Phil Di Loreto! You have always been an employee driven people leader.

Oliver Campey

Customer Onboarding at Clio - Customer Success ??

2 年

Really great article Phil Di Loreto You are a real treasure!

Phil, you hid your "struggles" well - my impression was you came out of the gate strong and had an immediate positive impact at Jane. It's been a privilege working with you over the past year.

Michelle Sadden, Prosci?

Senior Leader | Business Operations | Human Resources | Communications | Strategy and Growth | Caretaker to neighborhood squirrels

2 年

Thank you for sharing your journey. Taking on a stretch position can be exciting and scary at the same time and self doubt can be a loud voice. Some of the best career experiences I have had involved teams who gave me the room to try new things without fear. It sounds like Jane.app is a great place to do that.

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