Finance Advice I Wish I Gave Myself in My 20's


There’s a lot of life lessons to learn when entering adulthood, and knowing how to handle finances is one of the important. 

Math was one of my favorite subjects in school, but those were just hypothetical numbers, and didn’t translate to financial situations.

Real life money management skills, and forming healthy money habits, just wasn’t taught in school. For me, they weren’t taught at home, either.

I preface this article with a little information about my background.

I grew up in a small town, lower income family, living in a single-wide trailer. My father was disabled, which prevented him from having a job. My mother never graduated high school and worked an entry level job on an assembly line. They had no short-term or long-term savings, and not even a retirement fund. Talks about money were non-existent, except “it takes money to make money, and we don’t have any.”

I saw the look of stress and worry on my mom’s face, and heard her every morning being physically sick from working 60 – 80 hours a week trying to make ends meet and provide for my brother and myself. They were good parents, always putting their children first.

I just knew I didn’t want to live like that, barely holding on to life paycheck to paycheck. 

And so, at the end of my 20’s, knowing where I came from, I looked back at some of my accomplishments. I became a licensed insurance agent in multiple states, and top salesman for the company I worked for. I was a certified personal trainer, eventually becoming fitness club supervisor. I played in a band, and took it from nothing to being studio recorded, featured on nationally syndicated compilation CD’s, and playing large festivals in multiple states. I was the first person in my family to ever attend a college.

These are all things I should be proud of. But as I sat there thinking about things, penniless, I also wondered what happened. What did I do wrong? 

I thought I was smart, but when it came to life skills and managing money, I knew nothing. 

Everyone’s situation and background is different, but if I could turn back time, this is the finance advice I would give myself.

Entitlement Doesn't Pay Off

I entered the workforce as green as they come, but eager to prove myself. I took a job in the insurance sales field, working under licensed agents, and within a couple months I was a top salesman. The company took notice and offered an opportunity for me to become licensed, with them paying for the course and exam fees. 

I said yes and passed all exams for life, health, property and casualty insurance. I also received reciprocal licenses in other states. I could officially stop selling under other agents’ accounts, and have employees selling under my license. I was known as the “junior” agent since I was so much younger than my peers.

After being with the company for almost a year, I tried to get a promotion outside of sales, with a lot of support for my co-workers. The word going around the rumor mill was that I would get the promotion. Then the manager brought me in for what I thought would be my congratulations meeting, and instead I was told that corporate headquarters decided not to choose me.

I was shocked and upset. I felt entitled, like they owed the promotion to me, not even considering the other candidates with more tenure, experience and qualifications. So when I was told they didn’t choose me for the job, I looked at my manager and said “Then you can tell corporate headquarters that this is my 2 week notice. I’m quitting.”

I expected that hearing my answer, they would reconsider their decision, but that didn’t happen, and I soon found myself without a job, and without a plan. 

I needed money, so I took the first job (and a pay cut) I could find. Shortly after, I got laid off due there being a lack of work. I asked, how can I get “fired” when I’m doing a good job? Within a couple weeks they called me to ask if I’d come back, and I said to my manager “Didn’t you just lay me off? Clearly you don’t value me, so no, I won’t be coming back.” and I hung up the phone.

Those were my first 2 jobs, and thinking back, I made some pretty dumb decisions. In the end, I only hurt myself and my finances. A sense of entitlement doesn’t pay off. The world doesn’t owe you anything. You don’t always get what you want, but if you want something, you need to work for it. If only I knew that back then.

Pay Yourself Rent

When I got my first job, I still lived with my parents, and well, I took full advantage of it. They didn’t charge me rent, so when I got my weekly paycheck, I considered it to all be “my money” that I could spend on whatever I want.

It was selfish of me to not help my parents out, and got me in the mindset of spending money on the wrong things.

When I decided to move out on my own, I was totally unprepared. Suddenly a large chunk of my paycheck was going towards rent, which I wasn’t used to, and didn’t know how to adjust my lifestyle.

Had I been smart, I would have set up an account, or at least a box at home labeled rent, and paid it each month. This would have taught me how to live on less each month. Also, since I’d be paying myself, I would have a nice little nest egg saved up, which could have helped me with actual rent when I moved out, or if I had an unexpected expense or emergency (which I did).

Don't Buy on Impulse

I couldn’t wait for pay day. Why? Because that meant I could spend it.

When I was in my 20’s, money seen was money spent. I had a spending mindset and not a saving mindset, not understanding the future impact and consequences.

Each week, I’d cash my check after work, then say to my brother “Let’s go to the mall.” It became a tradition. Most times we went without looking for anything specific, just whatever might catch my eye. 

I spent a lot of money on things without any lasting benefit, or caring if it was on sale, or if I had a coupon. I see it, I buy it.

Most times, if I had just made a list of things I saw, or told myself to wait until next time we went to the mall, I probably would have changed my mind and not bought them at all.

Impulse buying is not only costly, but also a hard habit to stop, which I learned the hard way.

Learn to Cook

When I moved out of my parents’ house, I could no longer rely on my mom’s home cooked meals. Growing up, my brother and I also weren’t really allowed to cook. To say I was lacking experience in that area would be an understatement.

What does a single person do that doesn’t cook? They dine out. I spent the first half of my 20’s most days buying lunch at the cafeteria, ordering take-out, fast food, or going to a restaurant.

It doesn’t seem like much money when you do it, but just spending $10 – $15 a day on food when I could have prepared a meal for half that, would have saved me thousands of dollars a year.

Multiply that over the years, and I discovered it had a huge impact on my finances.

Save for Vacation Before Taking One

As I mentioned earlier, I grew up in a lower income household. That meant we couldn’t take vacation, or at least nothing outside a day trip. I didn’t get on my first plane until I was an adult.

When I got out on my own, I felt like there was so much for me to see and experience. I wanted to travel the U.S. and abroad.

So I did. The problem is, I did it the wrong way. I planned my vacation dates and location, but I did no financial planning. I just told myself, I am going “here” on these dates, no matter what. I would justify it by saying the money doesn’t matter, I’ll pay for it later once I get my tax refund, or when I get a bonus.

Since I didn’t have the money saved up, and couldn’t pay it off when I returned from vacation, that meant I had to borrow money, and pay interest, which made the vacations more expensive and more difficult to pay off.

On top of that, borrowing money also meant when on vacation I had to ask myself “what can’t I do?”, limiting my options since I couldn’t pay for it,  and not being able to fully enjoy the experience.

Vacations should have been a reward for being responsible with good money habits, which would provide motivation to continue those habits. Instead, they rewarded my bad behavior, and put me deeper in debt.

Have Proper Health Insurance

When you’re young, you feel invincible. Health insurance is for people who are already sickly, or for older people. At least, that’s what I told myself when I was in my 20’s. 

“Look at me. I’m fine. I’m healthy. I have enough bills to pay. Health insurance would just another bill, and a waste of money.”

And then it happened…I had to have emergency surgery.

I didn’t have the money to pay for it. I thought to myself, it’s no big deal. The hospital will forgive it. Besides, they can’t get what I don’t have, right?

I couldn’t have been more wrong. A few months later, the letters and phone calls started coming from a collections agency. The ironic thing was, the collections representative was one of my old acquaintances from my first job. It was fun to catch up, but as much as I tried, I couldn’t talk them into forgiving my debt.

It completely destroyed my credit, and I suddenly had a huge bill I needed to pay. It took the rest of my 20’s to settle the debt and repair my credit.

I thought I was saving money, but not having proper health coverage ended up being the most costly mistake I made.

Invest in 401(k)

I vividly remember the day when the company I worked for first brought in a finance manager to discuss investing in their 401(k) plan.

At the time, I knew nothing of investments, except my father warned me not to invest in the stock market because I could lose everything. I thought this was the same, just some guy trying to take my money.

And then he tossed out the word “retirement.” 

What? Retirement? I’m 20 years old. I could barely wrap my head around saving for the short-term, much less 50 years in the future.

I didn’t understand index funds, target funds, employer matching contributions, compound interest. Nothing.

I started investing for retirement when I turned 30, and felt like an idiot I didn’t start sooner. I’d already lost 10 years, starting from scratch, when I could have put myself in a good position during the years I had the least amount of financial obligations.

Find a Financial Friend or Mentor

We often make decisions based on those we surround ourselves with. Even as adults, we can be influenced by peer pressure.

Friends should help us make good decisions. Frugal friends should know when we can’t afford something.

Hanging out with friends who like to go to the most expensive restaurants, or always need the latest and greatest thing, will just cause you to spend more money.

Having a friend or someone you trust with like-minded goals and money habits can keep you accountable to ensure you stay in good financial shape.

If you don’t have someone to go on the financial journey with you, there are free apps now available that will answer any financial question. Want to know if you can afford that purchase you have your eye on, when your next bill is due, or how you can save for vacation?  Just send a text or ask a question with an app like Cleo or Charlie, and you’ll get a friendly and conversational answer, like a real person.


Like most of us, in my 20’s I had my successes and failures.

My path started off with bad money habits, not following a budget, and spending money instead of saving.

I wish I applied this advice back then, as it would have completely changed my financial outlook and helped me escape the paycheck to paycheck trap.

It’s also never too late to start. Our financial choices today affect our future. 

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