Save your first—or NEXT—$100,000!

Money Under 30 has everything you need to know about money, written by real people who’ve been there.

Get our free weekly newsletter and MoneySchool: Our FREE 7-day course that will help you make immediate progress on the money goals you’re working toward right now.

No, thanks
Advertising Disclosure

Money Mentors: Teacher and Entrepreneur Tom Morris on Working Multiple Jobs, Taking Risks

David’s post “Why You Should Work Multiple Jobs,” really got me thinking. Much of the advice in that post sounded like lessons I’ve heard since I was little.

Tom Morris (left) and his wife Alice (right) raised six children and ran a travel business.

David’s post “Why You Should Work Multiple Jobs,” really got me thinking.

Much of the advice in that post sounded like lessons I’ve heard since I was little. Many of my family members have worked multiple jobs (or at least a part-time job while being full-time students), and I have done so myself.

My grandfather is a terrific example.

That brings me to our newest “Money Mentor” post. They won’t all be personal, but for this one I’d like to introduce you to Tom Morris. Or as I call him … PopPop.

My grandfather worked as a math teacher for his entire adult life, and he still managed to send all six of his children to private universities, bring them on family vacations, and save for retirement.

How did he do it? By working multiple jobs.

PopPop told me during our interview that during the course of his life, he has worked 30 different part-time jobs.

His longest-running second job was a travel business he started during his second year of teaching. He organized trips for groups (most of them for senior citizens and students), usually by bus, to various locations across the United States and abroad. It was profitable and grew to be the third-largest travel company in New Jersey.

He now teaches seminars about entrepreneurship at local colleges. And he’s one of my most influential personal money mentors.

Maria: When David was first trying to get out of debt, he took a second job — a move that he recommends to others now on Money Under 30. I know this is a move you also made. Can you share your experience working multiple jobs? Is it something you would recommend?

Tom: When I got my first real job as a math teacher, my very first year after two months on the job, I said, “I want to do this the rest of my life.” I loved it. Now as the year went on, it was great, and then I came to the summer. And the summer, a teacher doesn’t get paid, so I actually started to panic because I didn’t know how I was going to get through the summer, which is a big problem for teachers.

My school had a painting program for teachers, where you would paint for the summer. And I did that the first summer. But halfway through, I became aware that we were making peanuts. … So I started thinking, “What can I do in summers besides this where I can make enough money that I can continue my teaching profession?” With about two weeks to go in the summer, I announced to my fellow teachers, “I am not going to do this next year.” And they were shocked.

And they said, “What are you going to do?” And I said, “I am going to take a group of students from our school across the United States next summer.”

When I got back to school I got together with another teacher and gave him my plan. … The next summer, we ran an ad in the local newspaper, and we had 35 students sign up from our school. This other teacher and I took them across the United States for three weeks. I had a lot of ups and downs after that. But that was the real start of my program.

Maria: Did you make any money during that first year?

Tom: We broke even on it. We didn’t make money, but it gave me confidence to know this has all kinds of potential. So I gradually started to realize that it could be more than a summer job. I could do this on weekends and eventually I said, “I can do this all year-round.” So that’s the motivation. And I learned the business just by doing it.

Maria: I know besides the travel business, you had other part-time jobs that were unrelated, right?

Tom: I did have 30 part-time jobs throughout my lifetime. … Some of them were only short things. One of the things I present in my entrepreneurship talks is that when you have a part-time job, or when you meet other people, [it’s good to think about,] “If I owned this business, what changes would I make? What would I do if I were the boss?” That is, I think, a good way to think.

In my entrepreneurship classes I recommend that … when you meet people you ask them about their job: “What do you like about your job? What don’t you like about your job? If you could make changes, what changes would you make?” It gets you thinking along those lines.

Maria: I think something that can hold people back from entrepreneurship is the fear that it won’t work out, and the risk involved. Did you have fears when you started your business?

Tom: Yes. There are three themes that run through my entrepreneurship talks.

The first: An average person can become an entrepreneur. I think that’s key because I think sometimes we think you have to be a genius, like Bill Gates or somebody like that.

The second thing: Ideas are in front of us 24 hours per day.

My third point: Small ideas can become big ideas.

When I first started, I had some reservations, you know? I had to keep saying to myself, “I can do it. I can get all this done.” I had some fears.

When I started, I was only doing it as a way to keep my math teaching job … My whole goal was, make enough money that I can continue to be a math teacher. And then as I got more confident as I was moving along.

Maria: Maybe having a shorter-term goal like that makes it less intimidating?

Tom: I think that’s exactly right. … It didn’t happen overnight. It was a gradual thing as I built up confidence, as my business got bigger and bigger.

Maria: Switching gears a bit, I know something you really made a priority was your children’s education. If you could do it all over again, would you change anything about that decision?

Tom: I would do exactly the same thing, the way I did it. I wouldn’t change a thing. I had six kids that appreciated what I did and didn’t take advantage of it.

And they helped. They all worked part-time jobs all the way through.

Of course I had the right wife. You have to work together and she had the kids a lot. She would help me write out the luggage tags [for the travel business]; she’d be on her hands and knees writing them all out.

Maria: Are there any other smart financial decisions you made that contributed to your success?

Tom: I loved mutual funds. And I made it a priority to put away some of our profits into four Vanguard mutual funds. When we retired, of course I had my teacher’s pension, but I thought that was one of the best ideas that I could come up with.

I had these funds over a period of 20 years and we had some luck because we had some good years in the late 80’s and early 90’s. There were some good years in the market when my funds really took off. So I have to admit I had some luck in it also. But I thought that was a very, very good strategy.

What do you think about Tom’s ideas? What are your thoughts about working multiple jobs? What was the most valuable lesson you learned from a job you’ve had in the past?

Published or updated on October 1, 2012

Want FREE help eliminating debt & saving your first (or next) $100,000?

Money Under 30 has everything you need to know about money, written by real people who've been there. Enter your email to receive our free weekly newsletter and MoneySchool, our free 7-day course that will help you make immediate progress on whatever money challenge you're facing right now.

We'll never spam you and offer one-click unsubscribe, always.

About Maria LaMagna

Maria LaMagna is a recent graduate of Northwestern University where she served as editor-in-chief of the university’s award-winning daily newspaper and studied for five months in Argentina. Before joining Money Under 30, Maria worked as a reporter for CNN and the Indianapolis Business Journal. Follow Maria on Twitter @MCLaMagna.


We invite readers to respond with questions or comments. Comments may be held for moderation and will be published according to our comment policy. Comments are the opinions of their authors; they do not represent the views or opinions of Money Under 30.

  1. Catherine says:

    I also like the concept of working multiple jobs. I’m an environmental finance consultant, and while the hours are pretty regular, it does require some travel, which can happen with relatively little notice.

    I’ve found that a good solution for me is to tutor (everyone needs help with statistics!). Websites like wyzant.com really streamline the process of finding clients, and I’ve found that it typically offers a fair amount of flexibility. The service takes a cut of your earnings, but you can still do pretty well, and work as much or as little as you’re comfortable with.

  2. When I got my first real job as a math teacher, my very first year after two months on the job, I said, “I want to do this the rest of my life.” I loved it.

    What a wonderful thing to realize early on in a career. There are so few people that ever get to this point…

    Maria, this is a wonderful interview, thanks for putting it together.

  3. Great tips. I’m a big fan of multiple jobs to help you succeed with your goals. Sounds like Tom had some big ones, sending all 6 kids to school!

  4. Faye says:

    I think Tom has great ideas in bold strokes.

    Teaching jobs often come with fairly regular hours. Be in by 7 a.m./8 a.m. and leave by 3/4 p.m. This is of course providing they don’t volunteer to coach a sport or organize a club, but both of those decisions would lead to additional income.

    I haven’t been able to figure out how to pick-up or start a second job when working 50-60 hours a week on a salaried job (no overtime) whose hours are erratic. Sometimes there’s night meetings 3-4 times a week,sometimes I’m rushing to handle a situation at 3 p.m. on Saturdays.

    I would love to see tips on a second-job for those of us with jobs that demand being on-call status.

    • Olivia says:

      Agreed. I am an attorney so I work anywhere from 50-100 hours a week! I would love to know what I could be doing on the side. While I do make a nice salary, I also have over 100K in student loans so I would love to get ideas of things I could be doing with limited time/flexibilty.

  5. Speak Your Mind