Retrain to Gain a Better Paying Job

One day, we spotted a neighbor tapping away in her backyard on a stenograph, those goofy little mini typewriters used by court stenographers. When we inquired what she was doing, our 30-something friend said although she still liked her librarian job, she wanted to diversify her skill set in case she ever wanted to leave. “And also it’s kinda fun,” she said.

In reality, the leap from librarian to stenographer isn’t really that huge. Both require being quiet and attentive, paying attention to detail, and good organizational skills. It’s a great example of retraining for a job where your skills can transfer. We don’t know what our friend makes as a librarian, but stenographers make on average more than $53,000 annually. Most could even freelance for depositions in private cases and make almost double that salary. It’s the kind of job that flies under the radar but apparently stenographers are always in demand.

Don’t Shoot for the Moon

Choosing a new, better paying career isn’t just about the money. It’s also about finding the right fit. Some common misconceptions:

  • You may be surprised to learn that the best paid government employee in your area is probably not the governor or mayor but very likely a football or basketball coach at a public university. Epidemiologists working to eradicate infectious diseases, civil engineers designing better bridges and electrical grids, even the president of the United States make far less than the $11.1 million the University of Alabama pays its football coach each year—and that’s in a state where the median per capita income is roughly $26,338.
  • We’ve also seen articles elsewhere suggesting good career moves include a stab at freelance writing or opening a restaurant. While these are both fine careers, I know very few people who are able to make a good long-term living as a writer or restaurateur. It’s true that writing requires very little initial investment, but unless you get very lucky—and hustle to find a good and reliable breadth of clients—it’s hard to make any real money. On the contrary, opening a restaurant requires a very large initial investment, and can pay off, but the odds of making it are slim. It is one of the riskiest endeavors we can imagine. Almost 60 percent of restaurants don’t make it past the first three years. Obviously, if you write the next Harry Potter or suddenly become a celebrity chef, you’ve made the right choice. But we wouldn’t bet on it.

As for steady careers, public or private, the best paying are almost all doctors:

  • Surgeon
  • Podiatrist
  • Pediatrician
  • Orthodontist
  • Anesthesiologist
  • Obstetrician and Gynecologist
  • Oral and Maxillofacial Surgeon.

However, you need decades of training to succeed in these professions—loads of specific skill building courses, certifications, licenses, etc. These aren’t exactly easy jobs to switch to midcareer.

Be Realistic

The above jobs may be hard to switch in to, but fret not! There are many great positions out there that need the skills you have, or that you could relatively easily acquire. An office manager for a small company is not that much different than an office manager for a huge legal firm or medical practice. It’s all about ramping up, networking, and expanding your skills.

The most concrete problem we run into when switching career paths isn’t getting a dream job, it’s that we usually wind up taking a position similar to our current job—the one with the unsatisfactory pay to start with that made us want to leave. But consider switching to some of the career paths below that have the potential to bump up your salary.

We know plenty of people who have switched jobs to now sell real estate. It’s relatively easy to learn the ropes and get licensed, and it’s the kind of sunshiny job that makes people happy. Although the market in your area will set the price range—and your pay range—no matter what the real estate market is, there will almost always be sales to make. An old Italian saying advises when things are at their worst, get into real estate: “When there’s blood in the streets, buy land.”

  • Skills needed: Networking. Every new realtor we know is constantly reminding us they have houses for sale in our area. It can be a bit much but they have to get the message out.
  • Pay: You’ll probably get a very low base pay and make your real money on commission. While volume sales are key, just one or two big sales could make your year.
  • Alternative: An experienced realtor can also take on work as a property manager. You’d be the go between for a property owner and their renters. True, it’s work fraught with peril. You’ll need a good network of clients and repair people, and a nose for who is going to be a good tenant. But it provides the kind of steady pay that will help keep you afloat during lean sales periods.

Dental Assistant
This is one of those jobs we don’t think about until the assistant’s hand is inside your mouth. And that’s really the test for if this job is a good fit for you. Are you OK to look into strangers’ mouths each day. If so, it’s fairly easy to get the required degree and training needed.

  • Skills needed: Computer skills and the ability to scrape goo off people’s teeth are the number one skills here. The second set of skills include having a good bedside manner, good organizational skills, being able to work in good cooperation with coworkers and the resident dentists, and, of course, a steady hand.
  • Pay: While the national average is just about $35,000, upmarket areas like New York will offer much better pay. Furthermore, getting on the staff of a high-end dentist will do you well too.
  • Growth: Some predictions have the field growing nearly 20 percent over the next 10 years. More people, more teeth.

Financial Planner
While we speculated earlier that it would be difficult to retrain from being an accountant to a movie star, having expertise in tracking and allocating money could, however, easily qualify you as a financial advisor. Whether you join an existing firm or launch out on your own, people with investment skills, knowledge, and good analysis will always be in demand.

  • Skills needed: You typically need a Chartered Financial Analyst degree or CFP Certified Financial Planner degree as well as a bachelor’s degree. Analytical and communication skills are key. Obviously, you need to be very trustworthy and be able to keep client information confidential.
  • Pay: $90,000 or more is typical, but with wiggle room down for working in smaller practices and up for working with big name clients or in bigger offices.

Trade Tech Jobs
Plumbing installers, electricians, tile setters, solar panel experts, gas engineers, cabinet makers, kitchen fitters, HVAC (heating ventilation and air conditioning) technicians—women rarely think of taking on these positions, and that’s too bad, because they’re actually good paying jobs with lots of growth potential. Every time a domestic or commercial structure is built or renovated, one or more of these jobs is needed.

  • Skills needed: Trade schools are plentiful and can help you get the technical skills and all the certifications needed. A general knowledge of or aptitude for putting things together (more like solving a puzzle rather than NASA style problems) will take you far.
  • Pay: It varies wildly from region to region, but we’ve known carpenters who essentially work during the summer and take most of the winter off—so they must be earning pretty good pay.
  • Variables: Getting started can be hard. You’ll need to build relationships with general contractors and construction firms to get your name out there.

Niche Manufacturing
You know those conventions and events you go to where you wear a name tag on a string around your neck? That string is called a lanyard. We heard of a young couple who started a company creating custom lanyards for these events. Through savvy and aggressive marketing, they were soon making more money than they could imagine just from those little neck strings. If you’re a packrat, there’s a good chance you have one or more of their products collecting dust in a desk drawer right now. The lesson to take from this is how to spot an opportunity, even if it at first seems really niche. So keep an eye out for what else can be customized. What else could be made better or cheaper or in a different way?

  • Skills needed: Imagination, drive, marketing.
  • Pay: The sky is the limit.
  • Variables: The most common type of niche manufacturing you see these days tends to be digital. Those aps on your smartphone are a lot like those customized lanyards: a new way of presenting an old product.

Life Coach, Teacher, Paid Mentor
If you’ve successfully run your own business, chances are you have developed some invaluable experience. If you have the right temperament, a network, and have a talent for teaching, you may find sharing your knowledge both monetarily and personally profitable. Many young executives find themselves lost and are looking for someone to show them the way.

  • Skills needed: Like a psychologist or counselor, you need to be a good listener, have an open mind, and have valuable real-world life experiences you can pass along.
  • Pay: This varies widely. If you have a psychologist degree, you could count on a much higher fee than someone with a degree just from the school of life. Also, be aware that many people actually give away their services in this sector for free, so you will have to compete with those.
  • Variables: We’ve known several professional journalists who have hung up their reporter’s notebooks in order to teach what they’ve learned. While they didn’t take a big pay jump, they did find greater personal satisfaction guiding young minds instead of disinterested readers.

You’ve heard some of our ideas, but what are some career-shift ideas you’ve been thinking about?

There are hundreds, thousands really, of great paying jobs out there to discover. If you’re looking for a new job, be sure to search the job listings at 

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