What I Wish I'd Known Ten Years Ago: Lessons Learned on My Path to Leadership

They say hindsight is 20/20. So when I recently sat on a panel that asked what I wish I’d known ten years ago, it got me thinking about how my own professional journey might help to illuminate the paths of others. Ten years ago, I was technically in the same role as I am now: VP of marketing. And yet, the role and how I operate in it is wildly different.

​Lesson 1: Don’t get hung up on job titles:

It’s not about the title; it’s about what you’re doing. Does the position bring you joy? Is it satisfying? Titles can indicate possibility, but they don’t dictate the reality of any given role. So much of it is about the place you’re at, the people you’re with, and what you bring to it.

Ten years ago, I was in New York and at a career crossroads. I was in the process of negotiating a new position that offered me an interesting opportunity for growth with a larger global company. When I gave notice, my current company made a counter-offer — a first in my career. Instead of getting angry or frustrated about my departure, they posed the question many employees long to hear: What would it take for me to stay?

Lesson 2: Get internal clarity before you seek external change.

When asked what would compel me to stay, I realized I hadn’t really even considered this option. Their question forced me to get clear about what I was seeking. What did I value? What did I need to be happy? To thrive? If I couldn’t answer that for myself, how could I expect any employer — whether my current one or a new one — to deliver?

It can feel a lot easier and more comfortable to run to another employer instead of figuring out how to grow in the position you’re in, but that isn’t always the best path to career advancement or personal fulfillment. Back then, I just assumed my employer would not be willing to provide me with opportunities to elevate my career, only to realize that the duty fell on me to speak up for myself and voice my desires and expectations. My employer is responsible for telling me how our expectations may or may not align and what I need to do to get to where I want to go. But it’s a dialogue, and we shouldn’t assume they just “know.”

Lesson 3: Be your own best advocate.

Because I had another opportunity in front of me, I got bold in a way I hadn’t previously. But you don’t have to wait. You never know the answer to what might be possible in any given situation until you are brave enough to initiate the conversation.

In hindsight, if I had been willing to confront my boss sooner, before I was already halfway out the door, I could have saved myself an enormous amount of time, energy, and stress. These conversations require a level of trust and bravery, but, as I discovered, the short term pain is well worth the long term gains.

After some difficult-but-honest conversations, I ultimately decided to stay in my current position on the condition they would invest in me doing an executive MBA program. For two years, I poured my heart and soul into that training, which opened the door for me to become COO of that company and later take on other positions and responsibilities I otherwise never would have imagined. And this all came to pass because I finally pushed myself to be brave and ask for what I needed.

Lesson 4: Initiate crucial conversations early and often.

Don’t avoid the difficult conversations; embrace them. The longer you wait, the harder it is. Do what you need to emotionally prepare so that when the moment comes, you can approach it with poise and confidence. The more often you do it, the easier it gets – and your relationships will be stronger for it.

Sometimes you can have all the conversations in the world, but someone still comes to you with an amazing offer that’s hard to pass up. Over the years, I moved from one exciting opportunity to the next. It was not unlike “dating around.” Breaking up and moving on to a new prospect can be very seductive. And just like with dating, experiencing diversity can help clarify what you do and don’t want in your position.

When I was finally asked to consider what it would take for me to stay, I realized they were asking me to commit to a real relationship, rather than simply dumping them for the next exciting thing. To answer that question truthfully, I needed to get clear on my core values:

1. I wanted a place that valued both marketing and me. Knowing I could be offered a seat at the table moving forward was important to me.
2. I wanted to operate in a culture of learning. Training programs, coaching, and deep conversations in everyday exchanges signal it’s an environment that is looking to develop the whole person.
3. I wanted work with a purpose. I need to be doing something that matters, something that makes it worthwhile to go to work in the morning.

A huge reason why I landed at XL is because it ticks all of these boxes.

Lesson 5: Align values and expectations.

Even a company with the best intentions or the most success in the marketplace may not be the right fit for you. Define your values and cross check them against your current or prospective employer.

XL Construction – Sonoma Academy

Even once you land at a company you love, in the role of your dreams, your work is not done. That’s at the core of embracing a growth mindset. Yes, you’ll accumulate a lot of knowledge (and hopefully a bit of wisdom) over the years, but the learning never stops. If you’re flexible and approach every day as an opportunity to grow, your ability to expand and advance — often without ever changing companies or roles — is limitless. Someone else’s journey is not your own, so the more you mindfully forge your own path, the happier and more fulfilled you’ll be.

Lesson 6: Commit to a growth mindset.

Getting the job is just the beginning. You don’t have to follow some linear career path you read about or saw someone else follow. Make your own way through insatiable curiosity and perpetual improvement.

These lessons brought me full-circle: from a position as the VP of marketing to another position as the VP of marketing. Along my winding path, I’ve had the opportunity to oversee not only marketing, but IT, customer service, HR, and business development. I got an MBA and challenged myself to get clear about who I was and what I wanted — and then ask for it.

Accumulating those skills allowed me to return to my heart and soul — marketing and communication — with a totally different skillset and mindset. It’s the same-but-different position that I never would have recognized or imagined ten years ago.