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1 Scary Convo and 3 Ways to Find More Freedom

1 scary conversation and 3 ways to find more freedom

Today I’m pulling you into a haunting conversation that I had many years ago about my funeral. Creepy, right?

It was. But it was a sobering conversation where I received some difficult but necessary advice I needed to hear that stays with me even now.

And it shifted how I approach my job, money, and, life, ultimately resulting in more peace and a delicious taste of freedom.


Many years ago, I was working at my first employer after college. It was an exciting time. I had a salary, my own desk, and even a key card that got me into the building. I felt like I was walking on air every time I came to work and I felt honored at all the responsibilities that were given to me.

Before too long, those responsibilities and the to-do list that came with them grew and it seemed like I never had enough hours in the workday to get everything done.

So I started taking my work home with me. I spent my days at the office, and I spent my nights on the couch in front of my computer, chipping away at my never-ending to-do list in the hope that, if I worked long enough, I could cross off that final item.

After many months of this, my manager pulled me into her office for our quarterly review. She asked about the job, how things were going, how I liked my time at the company so far, and more. She also asked how many hours per day I was working.

I felt a sense of pride when I told her that not only did I put in a full workday, but I worked many hours at night to get ahead… but her response was not one I expected.

I was shocked when she told me, “Jessica, you need to stop that as soon as possible.”

She must have seen the confusion on my face because she continued talking… it was the first time I ever heard of the concept of burnout.

But what stuck with me from that conversation was the picture she painted about my funeral.


She said, “Think about it this way… when you get to the end of your life and all your days are done, what do you want it to say on your gravestone? Do you want it to say “Good employee?” Or do you want it to say “Loving wife, mother, and friend?”

Do you want there to be a crowd of people who loved you surrounding you as you move on to the next life? Or do you want no one to show up? This is the reality of what you need to consider when you spend all your waking hours working for a company to whom you are just a number.”

It was jarring, but she was right. I was giving all my time and energy to a company that I was expendable to, and I was not giving time to the people who loved me, or even giving time to myself.

As a result, I made three shifts that ultimately changed my life and gave me the beautiful gift of more freedom.


The first thing I did was I immediately quit working beyond my agreed-upon hours… so at 5 pm, I was done. And I started using my nights and weekends to invest more time in myself.

Instead of spending my evenings doing work for my employer, I started spending my evenings doing “work” that would make me better.

Some examples include focusing on my health (I joined an intermural kickball team, I did workouts in my apartment gym, I walked trails with friends, etc.), taking classes (I started with a free financial course, and have since invested in some paid courses, as well), and spending time with people I love (friends, family).

It’s no big surprise that I immediately felt better, but as the months passed, I started worrying… what if my employer realized I wasn’t working as hard? Would they let me go? What if I couldn’t find another job?

That scared me, so I started doing something else with my free nights and weekends.


The second thing I did was start working on my finances so I would not have to depend solely on my employer for money.

I realized much of my stress came from either working too hard or feeling like I wasn’t working hard enough and then worrying that my company would lay me off as a result.

In both cases, I was worrying about aspects that were directly tied to my employer, so I decided to figure out a way to stop relying solely on that employer for money.

As mentioned, I started by taking a free class about retiring early. I learned a lot, but I realized that pouring money into my 401(k) would help me in my retirement, but it wouldn’t help me stop depending solely on my employer right now.

So I started learning how to create enough financial freedom in the present that I didn’t need my employer anymore… and I did this by asking other people who had done it, signing up for courses, reading articles, and working through any free resource I could get my hands on.

(Podcasting was not big at the time, but I can assure you, if it was, I would have been listening!)

So I learned about different assets I could invest in now that would pay me now so that I could have other forms of income beyond just my paycheck.

And the most incredible thing happened: once I had investments that were generating money, any fear and anxiety I had about losing my job evaporated. It made work so much more enjoyable because I could put in my hours and then enjoy my free time without fear. I knew that, even if my worst-case scenario of being laid off happened, I would be fine.

I cannot tell you how freeing that was.

Through this, it helped me with the third and final shift I made.


The third and final shift I made was that I had a major mindset shift. Before the conversation about my funeral, my identity was deeply attached to my job and my role as an employee of that company… and I didn’t even realize it.

That is a dangerous mindset to have because, if the job goes away, then you don’t know who you are. So not only are you facing financial hardship, but you also find yourself in an identity crisis.

Your job is just a job and, though it may be hard to hear, you are expendable to your company.

Once I realized I was just a number, my identity that was previously wrapped up in “Jess the Program Manager” suddenly became “Jess the woman, the friend, the human,” etc.

I didn’t want to die and be remembered as a Program Manager for that company. I wanted to be remembered as the girl who defined her own schedule, who spent her time the way she wanted to, who got to travel and work on the things she loved or take time off to be with the people who meant something to her.

I’m not saying don’t work hard… nothing meaningful comes without hard work. What I’m saying is to be intentional with where you put your efforts.

Do not forget that if it makes sense for a company to let you go, they will. So it’s wise to remember that and use it to prepare mentally and financially in case that ever happens to you.


Even if it seems grim, think about your funeral.

What do you want to be remembered as? What do you want your life to look like? And what changes do you need to make now to make that happen? The new year is right around the corner… are you living how you want? If not, how can you start?

Investing in myself and my finances gave me peace of mind and freedom I never thought was possible, and it positioned me to spend my days exactly the way I want to.

For me, a big part of that meant making time to prioritize my finances, and to figure out a way to help them grow without me needing to constantly spend extra time managing them.

The biggest thing I did that helped across the board was start organizing my money… I knew I was making good money, but I didn’t realize where it was going and I wasn’t ‘storing’ it strategically… in other words, outside of my 401(k), I wasn’t investing in anything that I could use now if I needed to.

The way I got organized was by creating a financial dashboard, more commonly known as a budget. This gave me the information I needed to see where I could cut expenses, what I needed to put in my Emergency Fund, and how much I could afford to invest.


If this sounds like something that could help you, grab your free budget calculator.

It’s what I’ve been using for years and it is my favorite financial tool and, in my opinion, the most powerful of all.




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