Here’s the one sure thing to expect when you level up

Tosca DiMatteo
Oct 21
9 min read

My desire to level-up my life in many areas started at an early age and still hasn’t stopped.

I often felt less than and left out because I did not fit any 'standard beauty' image. I wanted to feel unconditionally loved and accepted.
I witnessed career paths with self-imposed limitations. I wanted to believe in bigger.
I used to joke and say; “I need to make friends who have awesome vacation homes.” The Truth? I wanted to BE the person with that second home.

My desires have led me to learn a lot about how to level up and navigate change.

After all, leveling up means something within you must level up first.

Here’s the funny thing about leveling up, honoring what you want, and saying yes to the change you’ve been dreaming of – you are going to hit resistance along that path one way or another. Even if you were the one calling it in for yourself – the discomfort and the resistance will come.

Case In Point #1: A new kind of love

After my cat Bianca passed away in 2019, my husband lobbied for our next pet to be a dog. A DOG? I do love animals, but a dog is a whole different lifestyle kind of commitment. You aren’t putting food and water in an automated feeder and stepping away for 3 days. And what about my dreams of big work opportunities that take me around the globe where I can extend trips and see the world? And what about potty training and behavior training and walks, like every day, multiple times a day? You catch my drift? How would we figure it all out? Do I want this change in lifestyle?

Case In Point #2: A new job

In 2008 I moved to Manhattan to be with my boyfriend (now husband) and took a job based in Purchase, New York. I moved without all the details in place – from where we would live, to what the commute would be. What was important is I got that job! Before the first day of work, Ryan and I did the first leg of the commute together. We walked to the subway, took the ride a few stops to 125th, and walked to the Metro North (train) platform. We didn’t even do the rest of the commute, which would take me to White Plains, where I would then get on a shuttle to Pepsi Headquarters. Tears bulged in my eyes on that train platform. THIS IS A LOT. This is a long commute. Is this actually going to work? Will I be able to have a life outside of work?

Case In Point #3: A second home

Recently my husband and I had an opportunity to purchase a second home in rural Vermont. It was a place we knew, a place we fell in love with, and an area we became fond of. We crunched the numbers and there was possibility. As we edged closer to a purchase becoming a reality, you would think I would be getting more and more thrilled. But that’s not what happened. It felt daunting. Another home, hours away, with harsh winters! A home with grass. Grass that needs to be cut! And weeds that need whacking. A generator for crying out loud that needs to be serviced. And on and on. This felt unnerving. How would we figure it all out? Would I actually like this change in lifestyle?

The Difficulties in NEW

In all of these situations, excitement of the possibilities drove me to the options that ended up before me. My intuition, my desires, my life experience all led to the crossroads and new destinations that I found myself in.

And each time, the closer I got to the reality of these things, a whole other part of me took over. Instead of these things feeling exciting, they felt completely daunting and overwhelming.

The closer I got to execution, the more daunting the change felt. The questions moved from openness and possibilities about the future I was pursuing (like how amazing it would be to feel unconditional love from a puppy) to fear-based statements like:

I will have to give up my dreams.
I will have to take care of a whole second home – it’s going to be so much!
I will waste hours of my life commuting, and I will hate it.

When things feel daunting and overwhelming – here’s my council for how to find your solid ground…

Normalize your fear of stepping into something new

Our nervous system craves knowing what to expect. Because when we know what to expect, we will be more adept at keeping ourselves safe. When you accept that it’s normal for your red flags to start going up, and your ‘what if’ questions to run rampant, and your limiting beliefs to infiltrate your mind, I hope you find solace that this is part of the process. (for more on this tune into Ep. 30 on The Unlock Lab Podcast)

When you know you are running up against something that is a ‘first’ for you, has a new level of uncertainty, or is a new kind of experience there are ways to prepare yourself. You can do this by creating some rituals / structure to keep you grounded. This can range from a morning cup of coffee with yourself, to a journaling practice to get out your thoughts, to signing up for a class to move your body.

Grounding helps you to keep your mind clear, and your heart open. And in times of change, keeping an open mind and heart is exactly how you will get through with more clarity and ease.

Gather data, identify the truth, brainstorm what’s possible

When you're close to taking a leap, and up-leveling your life, not only will your own mind start playing tricks on you and feeding you lies (hello inner critic), but other folks who are even more afraid of change will project their shit onto you as well.

WHAT? Second home?! We are about to be in a recession, save your pennies!

WHAT? You don’t want a dog – they are so much work!

WHAT? Long commute, you’re gonna hate that!

The antidote to feelings of fear and the worries of the unknown are to look at the irrefutable truths. If you have a hard time like discerning the truth - you can also imagine all of the possibilities – beyond the worse case scenario that you are feeding yourself. If you have a hard time doing this, grab a trusted friend, mentor or coach to help you see what is actual fact and to create a list of possibilities.

Let life unfold, don’t try to figure it all out

When we're afraid and unsure of what the future will bring, we try to grasp onto the wheel and find a sense of control. We often do this by over-planning and having all the answers before moving forward. But it is in the allowing of the path to unfold, which is where you will discover the truth. It’s where you will find the clarity, and it’s how the magic can come in.

I was waffling for a long time about the dog idea, but all the while Ryan was in full-on search mode. Many months later, a picture from an adoption agency stole our hearts and 8-week old Siena was in our arms less than a week later. We didn’t have time to over think. We focused on the most urgent things; get the crate, the collar, the leash, some food and go from there. It’s now five years later and we have learned about being the guardian of a dog with each step we take. And I am grateful for having a new family member Every. Single. Day.

The Opportunity in Something New

When we choose to level up and allow for change, this is where our biggest growth will come from. It’s when we expand our heart and mind, and it’s where we learn the most about ourselves. Pay no mind to judging whether those new pathways turn out GOOD or BAD, when we give ourselves permission to step into the unknown, we give ourselves permission to truly LIVE.

I’m writing this with just under one of month of owning a second home. What I can tell you already is that I’ve settled into pure joy for all that is accessible and available to me now – the walks in nature, new community, and expanded creativity. The details – like how to maintain a hot tub (yes hot tub!!), replace a sliding door, and keep animals out of the trash aren’t stressing me out, they're keeping my brain fresh.

As for that job in Purchase…after 6 months of the multi-leg commute, I decided to go the route of driving and parking in the city. It certainly wasn’t all roses, but it gave me more control over my schedule. I’m not gonna lie, it was a challenging time in my career, and I learned a lot of lessons in logistics, company culture change, and moving to a new city. I wouldn’t trade it in for the world for what it taught me, for the friendships I made, and the experiences I gained.

We can tell ourselves a lot of horror stories about the unknowns that are ahead – but we can make the choice to allow new stories to take center stage about possibility, growth and opportunity. As leader, you have an incredible opportunity to help others do the same.

Applications to Change Leadership

As a leader, not only will you be asked to step into the unknown, you’ll have to bring others along for the ride with you. As such, it’s important to ask yourself a few questions about what’s happening in your internal world:

Is your own mind riddled with fear and doubt?
Are you experiencing feelings of overwhelm and a sense of doom?
Are you resistant to the vision, or the roadmap for getting there?

If you've answered yes to one or more of these, rest assured that’s absolutely normal. If you want to level-up as a leader, moving out fear and doubt is the first step and this will require an internal investigation. Dig deeper into what’s going with these starter questions:

What am I telling myself about the results we’re being asked to deliver?
What about the situation frustrates me, and why?
What's not in my control – and how is that impacting me?

From this new understanding of your internal dialog, you can choose the narrative and the intentions what will serve you and your team. There's a difference between begrudgingly moving forward and choosing to find the hopeful road in the journey ahead. I’m not saying wear a mask and a happy face – but rather find a pathway that others would like to follow you on.

Being forthcoming in your own feelings will go a long way to help normalize what others might be feeling, and create trust in your leadership at the same time.

Change leadership means you support your team to feel hopeful about the future. This is about bringing in optimism and possibility to the table, along with the realities of the challenges ahead – because again no one is telling you to paint a picture of pure roses. Optimism and hope must start with you truly feeling this way first. To help you discover possibilities, here are a few starter questions to consider:

What 5-10 positive outcomes are possible (even if you don’t think they are likely)?
What personal and professional growth opportunities does this situation present?
What am I excited to learn on this journey / project / initiative?

The Moral of the Story

Leveling up requires change. Pursing bigger dreams means entering unchartered territory, and this will inevitably bring up fear and doubt; aka resistance. Whether you are choosing to say yes to the love of your life, saying yes to a new job, or leading an audacious change – this is my love letter to you to stay the course of your uplevel. Trust the vision of what got you here. And lean into the growth that comes with it. Find acceptance that the uplevel will come with its challenges and that you got this, no matter what.

Leading Change Authentically

Here are three ways I can support you in finding more ease in upleveling:

Leadership Development Series: Masterclasses on staying grounded and resilient during change.
The Unlock Lab Experience: Facilitated group conversations to re-invigorate team engagement for the tall tasks ahead.
1:1 Leadership Coaching: Customized and efficient support to lead change and reach your career and business goals.

To start the conversation, schedule an exploratory call with me here.