The Financial Road Less Traveled

I think I’m getting old. I’m starting to hit that phase of life where I’m looking at the choices I’ve made and ruminating over the roads less traveled. I find myself wondering about the career I chose, the jobs I’ve taken along the way, even the relationships I’ve had. Along with all the general “What if’s,” I’ve been wondering about the financial “What if’s.”

What if I hadn’t changed my major in college (three times)? Would I have ended up in a different field that I loved or hated more than where I am now? Would I now be making better money, or would I be barely scraping by?

What if I’d married that other boy who now owns his own hugely successful business? Would I have been his first divorce (of the three he’s had so far), or would we have stayed together and now I’d be wealthy?

What if I’d started saving money with my first job at sixteen instead of blowing it on fun and clothes? Would I have a lot more money today, or a lot of regrets about the fun times I missed?

What if I’d taken that higher paying job instead of going back to graduate school? Would I have enjoyed the job more than graduate school (which, for the record, I hated every second of), or would the high pay have meant high stress and an early ulcer?

What if I’d spent that summer interning for the famous company instead of studying abroad? Would I have been offered a full time job after graduation that I could by now have parlayed into a big career with attendant big money, or would they have cut me loose after the internship, making me regret giving up the time abroad?

What if I hadn’t taken the job that so beat me down mentally and physically that every job thereafter seemed like a nightmare? Would I still have been inspired to go out on my own, or would I be content working for someone else?

What if I had bought the larger house that would have stretched me in the early years to make the payments? Would I still be in it, easily making the payments by now and enjoying the extra space, or would it have snowed me under and ruined my finances for years?

What if I had… Well, you get the point. The list of things I could have chosen to do differently is long. Of course I’ll never know the answer to any of these what if’s, but I don’t think I’ve chosen badly over the years. I’ve ended up in a good place.

It’s just that every now and then I wonder if I made the best decisions. I wonder how much wealthier I might have been, how much happier, how much more successful. Of course there’s a flip side, too. I might be worse off than I am now, unhappy, poorer, and a complete failure. Given the uncertainties, I think I’ll take the way things have turned out. It’s fun to fantasize and wonder, but I wouldn’t trade my life today for a “maybe.”

But let’s say that I really want to go back and do something differently. Can I? Once you’ve chosen a financial road, can you ever truly undo or redo that choice? I don’t think so, and here’s why.

When you make a choice, you make it at a given moment in time, under a specific set of circumstances, with a certain amount of information. For example, when you choose one job over another, you’re a certain age, with certain responsibilities, a certain amount in the bank, and a certain amount of experience. You make a choice that will meet your needs under those circumstances. The job is also specific to that moment in time. It pays a certain amount, has a certain set of benefits and responsibilities, and certain people will be your coworkers and your bosses. Ten years down the road and all of those things will be different. What you know about yourself, how the world works, and business will be different, too. Everything will have changed so, naturally, your choice can never turn out the same.

Let’s say you chose job A over job B when you were twenty-five years old. Ten years down the road, job A no longer cuts it and you wish you’d taken job B. You fantasize about how much fun job B would have been, how great the people were who worked there, how much money you could have made, and how nice the atmosphere was. You decide to try to step back in time and go get job B.

Even if you could go out and get that exact same job B tomorrow (which you probably could not, but let’s just say you could), the results wouldn’t be the same as they would have been ten years ago. The money is probably different, the benefits aren’t the same, and the people you’ll be working for are different. You’re different, too. You’re older, you don’t think the same way, and your needs are different.

Would job B fulfill you in the same way at thirty-five as it would have at twenty-five? Probably not. You might enjoy it, but it wouldn’t be the exact same type of fulfillment you’d have had under the earlier set of circumstances. Or, being a different person now, you might hate every second of it and wonder what you ever saw in job B. No matter what you do, your future will not turn out how it would have had you chosen job B the first time around.

I think that once you make a choice, whether financial or otherwise, all the other roads become closed to you. You might be able to go back and live some of your choices in a different way, but the results and your future will never be exactly as they would have been had you chosen differently when you had the chance. It’s like the example financial advisors like to throw out about saving. The kid who starts saving at eighteen and saves for six years and then stops has more money at age sixty-five than the guy who starts saving the same amount at age twenty-four and saves until age sixty-five. While you can change your choice six years down the road and decide to start saving, your results will never be the same as they would have been if you’d started saving at eighteen.

Of course, you can change your choices at any time and take a different job, start saving money, buy a different house, divorce the guy you married and go marry your wealthy college flame (if he’s still available), or go back to school to major in your true passion. That’s the joy of life; you can change things anytime you want to and start to create a different life for yourself. You can start off on a new financial road whenever you choose to, but you can’t really go back and choose the road not taken. No matter how successful your new choice becomes, you will never achieve the same level of success, fortune, fame, or feelings as you would have the first time around.

I don’t say this to be depressing, but to deliver this piece of wisdom found in the middle of my own mid-life crisis. Make your financial choices as carefully as you can when you have the chance. No, you can’t see the future with absolute clarity, but try to think about what you might be giving up and where your choices might lead you.

Choose your jobs, your savings strategies, your education, your debt level, and your relationships with care. Don’t think that if choice A doesn’t work out that you’ll just go back and pick choice B because you can’t. It will never turn out the same. Once you make a financial choice, all the other financial futures that might have been in that moment are closed to you. All you can do if you mess up is to choose differently the next time. Once you pass the fork in the road, you can’t go back; you can only approach the next fork with more wisdom.