We’re excited to introduce you to the always interesting and insightful Jessica Tolar. We hope you’ll enjoy our conversation with Jessica below.

Alright, Jessica thanks for taking the time to share your stories and insights with us today. What do you think matters most in terms of achieving success?

I love this question because it can vary so much depending on whom you ask.

When most of us think of success, money comes to mind. Maybe not a specific number – maybe just ‘a lot’.

But the reason we think money = success is because many of us subconsciously equate money to happiness.

That’s really what we’re all after at the end of the day, right?

However, in my experience, no amount of money will ever make you happy.

I learned that when I finally hit (what I thought was) a critical salary goal I’d been chasing for years.

It’s what you DO and CREATE with that money that matters.

Money is simply a tool we can use to create fuller and richer lives… in the non-monetary ways that count.

A critical piece many overlook is that money can give you more freedom, and more freedom can grant you more happiness.

Because freedom empowers you with self-sovereignty.

You get to decide what you do, when you do it, where you do it, with whom you do it, and for how long you do it.

And it’s an incredible way to live.

I do believe a certain level of financial wellness is needed to achieve this.

But, more importantly, I believe to be ‘successful’ you must first realize that money is not what makes you successful.

It’s what you DO with the freedom that money gives you that defines your success.

Jessica, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My name is Jessica Tolar. I grew up in middle-class America, went to college, worked in tech for 10 years, bought a house…

and then quit my job and moved to El Salvador.

A couple of financial scares during my corporate career woke me up to the realities of the financial system and scared me just enough to pay closer attention.

I got serious about investing during that time, and evaluating what I really wanted out of life.

And I realized I didn’t want to climb the corporate ladder. I wanted to LIVE.

I did not want to live a life where I had to trade time (literal moments of my life) for money.

And investing was my one-way ticket out.

I learned that if I did nothing with my money, the value would continue to decline over time due to inflation, whereas if I invested, I had a much greater chance of growing that value.

And it worked. And it was INSANELY empowering and freeing.

And, as a result, I want to share it with others, which is why I founded this business.

Investing has this stigma around it. It usually brings to mind a bunch of old white guys in suits – which I have nothing against (heck, I’m married to a white guy who will eventually become an old white guy), but it’s a little intimidating for some of us to try to break into the space, especially young women.

My goal is to make investing more fun, easy, and approachable.

And the reason I love doing this work is because I believe a world where no one HAS to do work they don’t love to collect a paycheck and where, instead, everyone spends their time working on what fills them with the most joy and purpose is a world that will finally know peace.

And I believe the fastest way to get there is through individual financial independence and freedom.

So, it’s my mission to help you define a practical plan that empowers you with the confidence to exit any situation that no longer serves you so you can move into a new chapter of your story where deep purpose, contentment, freedom, passion-based work, independence, and presence intersect to create a fuller and richer life.

I offer one-on-one consulting, two-on-one consulting, and a DIY go-at-your-own-pace online course to help you get there.

What’s a lesson you had to unlearn and what’s the backstory?

I had to unlearn the generally-accepted definition of ‘success’ in the United States, which is to have a huge house, fancy car, nice clothes, a pool, and swanky vacations.

I was very much on this trajectory and it wasn’t until I bought a second, bigger house with a new salary I’d acquired working for a company I did not like that I stopped to think: “What the heck am I doing?”

I’d just agreed to pay two mortgages (because I didn’t sell my other house) and basically further secured my position in the rat race. Financially speaking, I’d figuratively put myself in a jail cell, locked myself in, and threw away the key.

Why the heck would I continue working for a company I did not like? Well, because ‘I had bills to pay.’

And why did I have all these bills to pay?

Because I bought a bigger house which increased all my expenses. Not only did I just add a second mortgage, I added all the bills that come along with that (electric, water, internet, maintenance, furniture, etc.) on a larger square-foot house, plus property taxes, etc. – you name it.

So I had to unlearn society’s definition of success and decide for myself what success is – and, for me, it’s freedom of time and location. The freedom to do what I want, when I want, where I want, with whom I want, for as long as I want.

And working a 9-5 job I didn’t like to pay two mortgages wasn’t it.

Can you tell us about a time you’ve had to pivot?

Once I unlearned society’s definition of success and defined my own, I had to pivot in life – and it took some planning.

It wasn’t like I just decided one day that life wasn’t for me, quit my job, and moved to the tropics.

I knew that the transition would take time and money, and so, my first step was to save up 6 months’ of living expenses for emergencies.

Once I did that, I started investing to allow my money to grow as much as possible.

Once I had both my emergency fund and a nice little nest egg also in my investment account, it gave me the confidence to walk away from my corporate life so I could take some time to figure out what was next for me.

Literally ‘buying’ myself some time to just pause and reflect on what I needed was priceless.

And it led me to El Salvador – a place where I feel I can truly LIVE. A life among nature, by the sea, surrounded by mountains, where I don’t have to pay an arm and a leg to survive. And it’s a beautiful way to live.

Contact Info:

• Website: https://www.jessicatolar.com
• Instagram: https://www.instagram.com/jessicatolarinvests/
• Facebook: https://www.facebook.com/jessicatolarinvestments
• Linkedin: https://www.linkedin.com/in/jessicatolarinvests/
• Other: Investor Prep School: https://jessicatolar.com/investor-prep-school