5 Things I Wish I Knew Early In My Career

I spent this past holiday weekend with close friends who have three teenagers. I know when you hear teenagers, you think you know where this is going, but truly you don’t. They are three of the coolest teenagers I’ve ever met, so I was simultaneously taking copious notes and wholeheartedly grateful for friends who experience every parenting milestone before me and share the goods. Our "nieces and nephew" are smart, curious, interesting and interested in others around them. 

They have their entire lives and careers ahead of them. I was so excited for them and their collective potential that I found myself giving a TED Talk at every turn. They humored me, even asked insightful questions, but to be honest—even I was tiring of the Rachel B Garrett Career Boot-Camp Intensive Weekend by day three. So on that day, I decided to chill the F out, ride a lawnmower tractor (when in the suburbs!) and get curious about my need for a career monologue. 

It comes down to this: I don’t do regret anymore. That said, seeing these fresh faces and wide eyes, I wanted to give them all of the answers to the test. The secret shortcuts. The map to the landmines. All of the stuff I needed to figure out by failing and failing hard. Ironically, by spoon-feeding it to them, I would be robbing them of the opportunity to truly learn the lessons. Instead, I’ll distill them into themes I wish I knew when I was just starting out in my career…and we can see what happens from there.

1. We are in a time of inequality, but you can work to change it. 
Growing up a privileged white girl, I was taught (and believed) we fought for and won equality on many fronts. My dad was an entrepreneur and on both sides of my family, self-made relatives were evidence to me that the American Dream was alive and well. What I neglected to see at the time was that all of these relatives were white men. When I, along with colleagues and friends, began to experience both overt and subtle gender discrimination in our early careers—even with our feminism primers in college—we were still nothing short of shocked. While I’m glad nobody sat me down to definitively tell me what was possible for me and what was not, some middle ground advice would have been helpful. I have a lot to learn in this process, but so far, my approach with my daughters and in my workshops has been, "Let me teach you the tools to advocate for yourself, be a leader and create your life with your choices…in the context of our patriarchal culture fraught with institutional bias." I’m fighting for a world where I don’t have to say things like this, but if you’re a woman, that may mean something as simple as smiling while negotiating and working through your discomfort with self-promotion, so you gain greater visibility in the organization. And for the professionals of color in my workshops, it’s listening to what they need, supporting them with the tools, and providing a safe space to talk through the inequity so they can be the leaders and change-makers in their organizations.

2. Growth is the new perfection.
You’ve heard me say this many times, but perfection is unattainable and is a pointless goal. Growth is the goal. It could look like a world where every failure and mistake is an opportunity to learn, or where there are no wrong decisions, or where we seek out roles that constantly challenge us to learn instead of settling in where we get comfy and stuck. I wish I knew or trusted this idea throughout the first part of my career. I was doing the same kind of digital marketing work over and over again—building new websites and digital experiences. I was hungry for growth, but it felt messy and uncomfortable. The opportunity to focus on growth also allows us to move at our own respective pace to get to our destinations. When growth is the goal, we need not compare ourselves to others in their own (often faster) processes, on their paths. Apples and oranges, friends—and not worth the time comparing. 

3. Follow your curiosity. 
In college I changed my major five times. FIVE TIMES! When I look back to that time with compassion, I realize there was an epic four-year battle between my curious and practical selves. I was prone to epiphanies (still am) and would let my new intrigue lead until my practical hammer came down to redirect my course. When my 5th and final major was chosen—Psychology—the exact same as my first, I secretly wished I was majoring in some kind of writing, but thought, "What are the chances that I could become a writer?" It seemed foolishly optimistic and full of myself. What I didn’t realize at the time was that a creative writing or journalism degree would have been a solid foundation for any number of careers—just as my psychology degree proved to be. And I could have spent all those college years solidly practicing a craft I love and have only late in life given myself the time and space to pursue. 

4. Nurture self-awareness early and often.
Do your early due diligence to figure out who you are and what’s meaningful to you, and continue to ask those same questions as you change. Be courageous when what’s meaningful to you is not the popular thing. It’s what makes you, you! The earlier you develop this honing device, the greater clarity and confidence you can have in your decisions. The clues about who you are also may come from the most unlikely of messengers. I had an eye-opening moment in college, when I made a joke that something (I can’t even remember what) went against everything I stood for and one of my jackass guy friends (there were a few) commented, "You don’t stand for anything." While it felt like a gut-punch, in my sophomore year of navigating my social world, he wasn’t wrong. It prompted me to ask the questions, "What do I stand for? What’s important to me?" And that was another moment when I became involved in feminism, an ongoing thread in my career. 

5. Humanity over hierarchy.
Early in my career, I got hung up on the differences between my VP’s and me. At the internal networking events I stayed with the people at my level and when I did break through and talk to more of the senior leaders—I’m not going to lie—I said some stupid shit. There were a few leaders along the way, with strong emotional intelligence, a clear generosity and a will to take their time in de-icing me—and those are the mentors and memories that stick with me. There was power in knowing I made a connection and saw above the fear that was holding me back. Sometimes I’ll spend a moment wishing I was able to do that more often early on, but I’m also grateful to have learned it in my career at all. I love how as a business owner, out of the hierarchy altogether, I’m able to see how unimportant hierarchical pretense is when it comes to human connection. We all want to be truly seen and heard—and if you can do that with the person next to you, your title is the last thing on anyone’s mind in that moment. 

With at least three decades of career ahead of me (I’m planning a late retirement—if at all!), it’s a wonderful time to distill the lessons down to a plan I can follow and change over time. Most importantly, just as I no longer allow regret, I also practice releasing judgment for my younger self—especially when she changed her major yet again in her senior year. She/I/we were confused. But now, with greater clarity and confidence in who I am, when I address her with compassion, the lessons follow and I savor them as they come into focus.

The Pleasure You Can Find In Presence

If you’ve been following along the last couple of months, you know I’ve been delivering a series of corporate workshops with a leader in my field who has become a mentor and friend. I’m learning so much in a compressed period, it feels like I’m either getting my Masters, in the first 90 days of a new job, or both—at the same time! Yes, definitely both! 

I’ve learned new rituals and tools to ready myself for each workshop, and I’ve put in multiple hours of prep for each and every one. I know it won’t always be like this, but this is where I am right now, and I have released any judgment I once had about what my intuition is telling me I need right now. Because the truth is, it’s working. I’m standing in my power and my confidence, and my audience is moved. They feel inspired to lead as WHO THEY ARE after our sessions and that is why I do the work. 

That said, all of the prep and the focus brings a certain level of intensity to my life that can be at odds with the peace I often seek. It’s finally 65 degrees and it feels like I’m still weighed down by my puffy coat, except it’s as heavy as a fur and I don’t even wear fur. As my biggest workshop to date approached for the senior most women in a financial services firm, the pressure hit a fever pitch. I found myself wishing it was over—mentally traveling to a moment in the future where it would be done, so I could remove my coat. 

The morning of the event, in my smartest emerald green dress, I stepped onto the subway nearly two hours early. A seemingly random—but not random at all—memory struck me. I was brought back to my 2014 New York City Marathon training, the culmination of which shifted the course of my life. During one of my five weekly training runs, I ran into a friend who’s completed several half and full marathons. I told her my training was going well, but I was so nervous about the race. What if I fall? What if I can’t make it? What if…? What if…? She put her hand on my sweaty shoulder and said, "You’ve already put in all of the hard work! The five months of training is the hard part. The race is your reward!" It was just what I needed to hear back in 2014 and…in that moment as I was on my way to train a room full of powerful women leaders. 

The race is your reward. 

I’ve done the prep. I know my content. I know who I am. I know why I’m here. Now, I can be present. I can enjoy every moment of my reward. I will take in the pleasure of being exactly who I am, serving just who I want to serve—contributing my part to a problem I see in the world. What else is there, really? 

By wishing it was over, and getting through it just to tell myself I did it, I almost missed the best part! Instead, I stood in front of a room full of rapt faces, opened with one of my favorite stories about my girls, and breathed in every single possibility that exploded in the 90 minutes that followed. 

Find The Clues To Your Next Career Move

Ten years ago, I was in a Digital Marketing role at a large financial services firm. After a successful career building websites and digital experiences, I had a stomach churning feeling that I was ready for my next move. I knew I wanted something different, but I had no idea what it could be. I felt stuck, disappointed and like I should have this figured out already! 

In that space of uncertainty, I decided to get involved in the many other activities available at my organization. I became active in the company’s women’s leadership development and networking group. While in the network, I connected with powerful, female leaders at all levels of the organization. A year into my work with these incredible women, I became pregnant with my first daughter, which sparked the idea to create a Workplace Flexibility event. We invited the most senior female leader in the organization at the time for a keynote speech, with a follow-up panel conversation about the organizational needs of working parents and the direction workplace flexibility was headed. I worked tirelessly to coordinate the event details and promotion on top of my day job. I was LIT UP by the process, the momentum and the excitement that grew with what seemed like a movement my colleagues and I were building. 

The day of the event I was 9 months pregnant and feeling my strongest pregnancy symptom—EMOTION. I pinned the lavaliere mic on our keynote before her talk and walked to the back of the room to take in what I along with my co-conspirators had created. A standing room only, packed audience. An energy that was hopeful and supportive and HUNGRY to know more. Our speaker started her talk with a heartfelt working parent meltdown story in which her overwhelm had caused her to forget something for her son’s class. In that moment where priorities came into the foreground, she chose to spend the extra time doing right by her family instead of attending the senior level meeting to which she was already late. 

I looked down at my growing belly, riveted by her words and taken with the intense energy of the room. I felt more alive that day than I had in many years of my digital career. Something shifted. All the clues for my next move were right in front of me, but I couldn’t see them. I was fearful for how I was going to juggle work and family in my own life. 

After my daughter was born, I started a new Digital Marketing role that was part-time and flexible. I knew it was a safe move, but also that it was the right move for me at the time, given my priority shift. I was able to work with great people, use my strengths and years of expertise AND control my schedule. My friends who were struggling to stay afloat would remind me often that I had the dream situation for a working mom. And for the most part, that was true. But there was something nagging at me throughout this time. It showed up when I mentored some of my colleagues and coached my friends through their career challenges. It was there when I presented to a room of employees and felt comfortable being myself, sharing stories to demonstrate my point. Or when I obsessively read articles about the disparity between men and women in senior leadership roles and the gender pay gap. When Anne-Marie Slaughter’s Atlantic article, "Why Women Still Can’t Have It All" appeared in July 2012, it rocked my world and was all I could talk about for days. All the clues were there, but it took time and space, supportive people and running a marathon (yep, best rut-busting tool out there!) to get me to trust the evidence and build a case for my career transition. 

When I work with clients who are seeking clarity about their next step, I say, "It’s OK not to know right now, but walk through your life with an openness to finding the clues, and when you find them, notice how they feel in your body." If you’re stuck in your head, listen to what your body is telling you with butterflies, or fireworks or flow. 

My clients create a list of past projects, programs, conversations and brief moments when they felt ignited, curious and alive. And then they open their eyes to the moments they brush off in their every day life as "silly" or "nothing." They know those moments were something and by acknowledging them and giving them space to grow—who knows if that something can turn into THE thing. 
 

A Thank You To My First Mentor

When I was nine years old, my mom returned to the workforce after a 13-year career break. Financially, we were struggling, so my parents decided to forgo finding an afterschool babysitter. Instead, I became your stereotypical eighties latch-key kid, walking home from the bus stop on my own, with a Papa Smurf keychain that said, “Don’t Lose These Keys!” and an afternoon that was a blank slate. 

Having grown up to that point with a stay at home mom, I struggled with all of the new-found freedom at first. In the first few weeks, I called my mom two or three times an afternoon—and you can guess how this went over with her employer. She had to cut me off, limit me to one 5-minute conversation and then I was left to figure out how to fill the rest of my afternoon. 

Then it happened. I found myself an inspirational mentor I could check in with five afternoons a week at 4PM, Eastern Standard Time. 

Oprah. 

I was riveted by her energy, optimism and belief that anybody could be anything and that anybody could get through anything. 

I was taken by the confidence and authority in her words—even when she didn’t look like anyone else I saw on TV. Already at nine, I was aware that my body was bigger and different than most of my classmates, so to see someone standing in her power simply as herself was a tremendous relief. I was grateful to know that this was possible. 

My relationship with my mentor grew over time. On the days her show was a bit sensational for my taste, I simply used it as background fodder for snacking and homework. But the days when she dug into the human experience: resilience, persistence, empathy, compassion, finding courage to stand in your convictions—I was hooked. 

I leaned most on that personal leadership foundation built during my mentor sessions in the initial weeks after my parents died in a car accident when I was eleven. I went to therapy and had the unconditional support of my extended family—but it was the Oprah Kool-Aid that truly kept me going. I’d seen first-hand how people could survive the most horrific tragedies and live to talk about it on the show. I often thought about how I would share my story with Oprah, and how she might grab my hand and tell me that I was brave. In that moment, when the rest of my family was reeling in grief and had no clue what to say to me, in my mind, Oprah knew how to be with me and I would feel in my bones that I was brave. I believed it. And it was that belief that started so small and grew to become all that I am. A survivor and someone who knows with every cell that anybody can be anything and get through anything. 

Looking back on that time now with my coach training, I know my conversations with Oprah televised in my mind, were my pre-teen version of visualization that kept me in the space of explaining my resilience, my compassion for myself and my belief that I was going to make it through. I remember keeping it to myself thinking I was either just a super fan or a little crazy—but that was actually quite an insightful strategy for an 11-year-old! 

Now that I’m in the business of helping people step out of their fears and into a life of their design, I call on my early training often and I’m certain that these were the days I first fell in love with this work. I’d be lying if I said I gave up on my mentor conversations. When I’m struggling with something in my business or in life, I picture myself in Oprah’s Santa Barbara backyard, filming our Super Soul Sunday episode and somehow, I always find my way back to being both brave and truly seen.