Starting Over Again at Age Eighteen

As I write this, I’m thirty six years old. My eighteen year old self existed literally half a lifetime ago. That’s scary to think about, that the person I was during my final year in high school, looking forward to a future education and eventually a great job and all of the dreams that I had, is half my age.

Looking back, there were a lot of things I did right. I managed to find a few good mentors. I went to a college that offered me a good scholarship. I had a lot of fun in college. I fell in love with a wonderful reliable woman. I got a great job after college. I had three great children. I eventually wound up in something close to my dream job.

At the same time, there were a lot of things I did wrong along the way, too. I accumulated way too much debt and I didn’t take that debt seriously for far too long. I’m still paying for that. I didn’t work hard to set up lots of income streams. I just made a lot of different missteps along the way.

Sometimes, I can’t help but think what I would do differently – and what I would do the same – over the past eighteen years if I had it to do all over again. Here are some of the major highlights.


I would go to college, but my primary consideration would be dollars and cents. In other words, unless I had a fist full of scholarships or I had someone else paying my way, I would spend the first two years earning as many credits as possible at the community college level, then finish up my degree at a four year college or university.

Why? That’s the cheapest way to earning a four year degree because many of your credits are earned at the much cheaper community college level, but you can still list a much more notable college on your resume when it comes to your four year degree. Just make sure that the community college credits you’re earning transfer to the target college or university that you want.

While at school, unless everything is paid for, I’d take advantage of everything I could to reduce the student loans I’ll be taking. I’d live in a very tiny room (after all, I’d need little more than a bed and a mailing address). I’d check into work study programs. I’d even have a part time job (a bit more on that later on). I’d live super cheap and eat as much free food on campus as possible. The goal is to leave college with the absolute minimal student loans I could possibly get.

I would study whatever major that would leave me most excited about succeeding in the classes and, if there were multiple majors that work here, the one that offered the best earning potential. Many college advice articles focus on going into fields that have a high earning potential, and while that’s good advice, it’s really hard to stand out in a field that you don’t care about. You want to be in a field where you’re excited enough and driven enough to stand out from the crowd.

Thus, I usually encourage people to identify areas that they’re actually interested in, then rank those based on earnings and dive into the field with the best earning potential. Maybe you’ll only come up with one. Maybe you’ll come up with fifty (that’s me). Whatever you come up with, research those areas and stick with the one with the highest earnings potential and employment rate.

I would join clubs that encourage transferable skills, as well as clubs related to my major, and get heavily involved in a couple of them. I spent a lot of my free time essentially goofing off in college. I was really only involved in one organization, but here’s the strange thing: a lot of my memories of having fun in college are connected to that organization, and my activities there wound up being pretty resume-worthy.

I’d look at all of the organizations at my school that focused either on transferable skills – leadership, public speaking – or on my major. I’d attend meetings of each of these and get involved with any and all of these that clicked with me at all. I’d try to take on leadership spots in at least one of these and preferably two.

Yes, this would eat up free time, but my experience has been that those kinds of activities were actually quite fun. Not only do I miss those clubs as a potential resume-builder and a good way to meet people, but I also regret the fact that they were simply fun to be involved with.

I would spend time getting to know as many professors in my department as possible in as many ways as possible. I’d go to the office hours for as many classes as I possibly could just to meet the professor and iron out any little thing I was unsure about … and also to ask more detailed questions than the class goes into. I’d stay at the end of class to ask questions as well if I had any. If there were ever any departmental events, I’d make sure to attend them. The biggest key is to make sure that your interest is genuine.

Why? Simply getting to know the professors in your department is golden. They can be a tremendous help when putting together a resume, figuring out what to do next with your life, getting into graduate school, or even finding direct paths to employment.

For the most part, college professors love to mentor young people who show some initiative and passion, and the best and easiest way to show that is to show up at lots of events and talk to them.

I would choose electives solely to build transferable skills. I took a lot of wasteful electives during my college years to fill out my degree. It wasn’t until near the end of my college years that I realized that those electives weren’t just space fillers, they were opportunities to build skills I would need in the areas where I wasn’t strong. I took a public speaking class and a technical writing class very near the end of my college years, and I found them both to be far more useful than any other elective that I took.

Yes, you can sometimes take these kinds of electives at the community college level to save money. That doesn’t change the general advice of choosing electives that will build useful skills for you that you can actually use down the road in your career.

I would use summers as effectively as possible. My first summer in college was completely wasted as I went back to my hometown and didn’t do anything useful. I did use subsequent summers somewhat better, but I still didn’t do as much as I could have with them.

My advice to you is to jam as much professional growth into your summers as you possibly can. Get an internship or some sort of job related to your major in some way. If you can’t do that, take summer classes. Fill your spare time with something related to your area of study, even if it’s just an independent project. If you can’t come up with an idea, talk to a professor about it – they’ll have lots of ideas and will likely help you more than you expect.

I would avoid any and all credit card debt. I left college with some credit card debt, mostly due to the last year or so where I started spending more than I should.

Credit cards are incredibly easy to get on a college campus. There are people everywhere offering things like t-shirts and beverages and other incentives to get kids to sign up for a card. It is really tempting to get one. Don’t.

If you do wind up with a card, try to avoid putting anything on it at all aside from things you would have to buy anyway, like textbooks, then pay off the full balance immediately. Don’t ever use it for a non-essential purchase. The last thing you want to do is leave college with even a drop of debt more than you’ll already have from the student loans.

Post-Graduation Money Choices

Starting over doesn’t stop at age twenty two when I hold a college degree in my hands. Many of my worst mistakes were yet to come.

I would still avoid any and all credit card debt. The biggest mistake I made was to rack up a lot of credit card debt in my first few years after college. I spent way more than I should and I ended up paying for that for many, many years – in fact, I’m still paying for it, because I’m missing tens of thousands of dollars I would otherwise have.

You can use a credit card if you’d like – they are useful for consumer protection and building up credit – but the second you use it to buy anything you wouldn’t otherwise just buy with cash, you’re making a mistake that you’re going to end up seriously regretting.

Never, ever carry a credit card balance if at all possible. Doing so amounts to allowing a credit card company to pick your pocket.

I would try to maintain a lifestyle as close to my low-cost college lifestyle as possible. The biggest reason that my finances exploded after college is that I bought into a huge amount of lifestyle inflation – and most of that lifestyle inflation was completely unnecessary.

If I could roll back the clock, I would try as hard as possible to continue to live like I did in college. I’d eat most of my meals cheaply. I’d make a lot of simple meals at home. I’d go out, but I’d look for ultra-cheap and free things to do. I’d rent entertainment rather than buy it (renting is way cheaper). I’d live in a small apartment with low rent and low utilities and I’d look for roommates, too. I’d drive a used car, probably the same one from my college years, and when it needed replacing, I’d stick with a late model used automobile.

I would contribute enough to my organization’s 401(k) or 403(b) to receive every dime of matching funds from day one. If your employer offers any matching funds at all, you should be contributing enough to your work retirement account to gobble up every dime of it. Matching funds are free money that your employer is just handing to you if you’re willing to reach out and grab it.

There is never going to be a better time in your life to start saving for retirement than those years right after college. You don’t have to save much then to have a ton of money when you retire, and matching funds make it that much easier.

I would also contribute enough money to my Roth IRA so that I am contributing a total of 10% of my income to retirement. If you take the idea of matching funds out of the picture, Roth IRAs are usually the best option for most people for retirement. You should contribute 10% of your annual income to your Roth IRA minus whatever your contributions are to your 401(k) in order to get matching funds there.

For some people, that might mean maxing out your Roth IRA. For others, it might mean very little Roth IRA contribution. Remember, the goal is to hit that “10% of your income” mark, regardless of where you put it. If you don’t know where to get a Roth IRA, I highly recommend Vanguard; it’s what I personally use.

I would eliminate any student loan debts as quickly as possible. If I had student loan debts after doing my college experience differently, my financial focus would be on eliminating that debt as soon as possible after college. I would make double or triple payments on that debt (preferably triple) and do that first, leaving me in a position to figure out how to live on the money that was left over.

This works hand in hand with avoiding lifestyle inflation. If you use your money wisely and live off of what’s left after you pay off debts and invest, you don’t have that much to spend. Couple that with an avoidance of credit card debt and you’re setting yourself up for a great financial start.

Post-Graduation Career Choices

Smart financial choices also extend into your career decisions after you graduate. Here are four moves I wish I had made (I did make a couple of them to a limited degree) when I started my career.

I would attempt to get a job in my major, but would accept any job quickly after graduation (while still hunting for a better job). This is the one part that I executed well after college – I landed a job in my field of study. However, it should be noted that I landed that job thanks to a professor that I had built a relationship with, so this did build on top of the earlier advice of connecting with professors in your department.

If I didn’t have that job, I wouldn’t just sit around unemployed for months. I would find some kind of work, even if it were just entry-level service work. Sure, it’s not a perfect job, but it’s a job that earns an income. My spare time would then be devoted to finding work in my field, as well as some of the other items below.

I would attempt to establish as many different income streams as possible while I still had lots of free time. You should never, ever, ever chain all of your income to one job. That’s begging for disaster. Instead, you should be using your free time to establish methods of earning money in other ways.

My oldest brother spends his spare hours on his lawn care business. He takes care of the lawn for a local church, a local cemetery, and several other establishments. My father caught fish commercially and raised vegetables commercially in his spare time. I’ve written books (which earn residual income) and recorded Youtube videos (which also earns residual income) in my spare time, and The Simple Dollar was launched as a side gig.

Find something that you can do well in your spare time and try to build a revenue stream from that activity. Not only does that give you more income right now, it also gives you a “fall back” if something happens in your main career.

I would establish a large and strong professional network by using social media, going to conferences and conventions to meet people, and joining professional groups. A strong professional network is probably your best tool for maintaining employment in your field. A good professional network shares useful professional advice, offers up employment opportunities and ideas, and often provides a pretty enjoyable time.

There are lots of ways to build this network. Within your office, be positive and avoid negative talk and find simple ways to help others. Outside of your office, establish a presence on social media (especially LinkedIn and Twitter) and talk to people in your field using those tools. If there’s a professional organization related to your field, join it. If there are conferences, conventions, or meetings related to your field, attend them. When you attend other face-to-face meetings, talk to people and share contact information with those that you click with.

I would put real time and energy into maintaining those relationships that I’ve built. Follow up, follow up, follow up. It’s one thing to meet a lot of people at a meeting of some kind, but the only way to keep building that relationship is to follow up. Follow them on Twitter. Send them an email reminding them of your interaction. Then keep doing it.

What I used to do was, whenever I got someone’s contact information, I always tried to leave the conversation with something to follow up on regarding that person. I needed to either send that person some information or ask about how some event in their life had gone. This gave me a reason to contact them at a later time after the meeting so I could share that information or so that I could find out how their life event had occurred. I usually jotted this initial reason for contact down on the back of the business card they gave me (or on the page of the notebook where I jotted down their info).

I also made an effort to contact them every once in a while, every month or two, just to see what’s up, and I’d definitely send a congratulations during a major life or professional event.

People that you’ve built a good relationship with will come through for you time and time again, both in ways that you see and that you don’t see. Keeping lots of positive relationships can do nothing but help you.

Final Thoughts

I am very happy with the life I’ve built and I have no real regrets about the past (other than perhaps a little bit too much debt). However, if I had it to do all over again, my path would be more along the lines of what I describe here rather than the path I chose to follow.

Every day offers you opportunities to live for today and live for tomorrow at the same time. I tend to find those opportunities mostly in connecting with other people, learning new things, and keeping my spending habits in check while finding inexpensive fun things to do. The time in my life that I’ve spent doing those things is time that I don’t regret spending in the least.

Good luck in wherever your path may take you.

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