Shawn Jenkins Blog

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Develop Your Skills and Talents

By Shawn Jenkins and Jonathan Mendonsa

I recently co-authored this article for my friend JL Collins’ blog. I thought it would also be interesting to share here on my blog


Have you ever considered your career to be like a brokerage account for financial freedom? You want to make the most of what’s in your account—or career—but you also want to do things to grow the account. In terms of a career, that translates to increasing your income.

Early in my career, I noticed that people with technical skills were making a lot more money than the rest of us. I started to look into why this was the case. It didn’t take long to realize that there was much more demand for programmers, project managers, and a host of other technical roles than there were people to fill them.

At the time, I was making $25,000 a year working at a non-profit. One day I took out a 3×5 index card and trimmed it to the size of a business card. I wrote on the card my goal: $100,000 annual income in five years. Above that I broke it out into $15,000 annual increases every year for five years. An unsophisticated strategic plan no doubt, but one that worked. I carried that card in my wallet for 20 years to remind myself that I can set and accomplish goals.

I had no formal technical education, so I went to Barnes & Noble and began buying books on Oracle database administration. I had learned Oracle was the leading database company and that many companies needed someone to manage their Oracle databases. I found out you could earn over $100,000 in this role, so that’s where I focused my self-directed training.

Sure enough, I developed my skills, snagged a job as an Oracle database administrator, and in my fifth year I made over $100,000. That career led me to start my own software company in 2000, which went on to become a publicly traded company worth over $1b.

Last year, I joined the blog with a new goal: to help as many people as possible achieve financial freedom (read more about this decision here). What I love about JL’s blog is that his approach to financial independence is simple: save as much as possible, get out of debt quickly, and invest in low-cost index funds. And my approach to growing my career was simple: identify a path that could earn me over $100,000 a year and then acquire the knowledge to achieve that.

A few years ago at JL’s Chautauqua event in Greece, I met Jonathan Mendonsa, the co-founder of ChooseFI. In speaking with Jonathan, I learned that he, too, had a simple system for developing one’s unique skills and abilities. He spoke about a concept of developing specific skills and stacking them up to make a layer cake of personal value creation.

Jonathan’s concept has been turned into a program that can enable you to obtain unique and very valuable skills and then turn those into potentially significant increases in annual income.

The great thing is that it doesn’t take five years, like it did for me, to acquire the skills and get into a career that will pay well over $100,000 a year. There are many careers in the technical arena that don’t require programming knowledge, coding expertise, or specific degrees.

I’ve asked Jonathan to share his idea and the story behind it here on the blog…

Jonathan’s Backstory


My name is Jonathan Mendonsa; I co-founded the ChooseFI podcast with my friend Brad Barrett. Prior to Starting the ChooseFI podcast, I was a pretty normal 28-year-old just starting my new job as a pharmacist after eight years in school. It felt good that I had landed a six-figure job, but I remember not being able to fully appreciate it. In the back of my mind, I knew I had spent the better part of my 20s accruing over $165,000 in student loan debt, and I’d have to pay back every penny with interest using after-tax dollars. It definitely put a damper on starting my career. From the outside, it looked like I should be thrilled, but I didn’t feel like I was winning.

I kept thinking to myself… There has to be a better way.

Be the Change You Want to See

I had the privilege of watching the ChooseFI community from the front seat, while also being afforded the opportunity to interview hundreds of normal people, just like me, who had started their careers in various ways. A pattern started to emerge, and what was at first a quiet voice in my head slowly became a calling.

This may be hard for many to accept, but simply put, the higher education model we were handed is fundamentally broken from an ROI career perspective. As recently as the 1980s and 1990s this may not have been true, but at the turn of the century, the ROI on education took a U-turn, with costs rising rapidly and wages barely keeping pace with inflation.

In 2020 I partnered with Bradley Rice to test this idea of skills vs degrees. I wanted to see if we could bring a new model for landing a job to the market.

In full transparency, 2020 was the perfect time to launch. We are living in an interesting time where skill-based certificate programs are in demand and employers are changing their hiring practices to reflect the growing lack of importance of an official college degree, while also embracing remote work as an expected practice. At the same time, people everywhere started to challenge the norms, searching for more truth, more awareness, and more transparency.

If we are being honest, employers have never really cared about your degree; it was simply their best gauge of whether or not you had put in effort to prove you were a quality candidate. With the emergence of certifications, skills training, and simulated experience offerings, employers had a brand new way to find high quality talent!

What employers have always really cared about is whether or not you can actually do the job!

With new skill-based programs, it was much easier to see who had the actual abilities, and that made it clear that skills were far more valuable than degrees. I know this as a small business owner—I don’t care about your degree. I need you to be able to do the job and/or train into it quickly. I also know I’m not unique in that vision.

Skill-based training programs have recently become more accessible due to widespread high-quality internet and the acceptance of remote training/working, which has caused a major drop off in the value of a degree. Employers realize that they would much rather hire someone with six months of targeted training than four years of general education, and when you think about it, it’s not surprising at all. College went from a great career choice to what is frequently referred to as the biggest financial mistake of many people’s lives. It was for me.

So, we built our very own skills-based program, and we named it Talent Stacker! The goal was to design a replicable system that would allow someone with no experience to qualify for highly compensated remote work, all in less than six months. We wanted to understand if there was a pattern to success, a repeatable process that hundreds or thousands of people could consistently complete. 

This was the question and the thesis. Over the past two years, we have proven this model definitively. We can enable you to break into a tech career in under six months by focusing on a five-step process. Watching this come to life has been fascinating, humbling, and rewarding.

Five Steps to Break into a Skill-Based Industry

There are five actions you need to take to successfully break into a new career (especially tech) without going back to school and getting another degree.

#1 Get Certified

From AWS (Amazon Web Services) to Oracle to Salesforce, there’s no shortage of certificates that can be obtained within a short time frame, usually within one to two months depending on time invested. The certificate acts as a minimum gate between the applicants and the job. Combined with the other tactics, it effectively replaces and surpasses the need for a generic, unrelated general degree. And it gives the employers confidence that you can do the job.

 #2 Build Your Personal Brand

The resume is secondary to building a strong personal brand that screams to recruiters, “This person loves this industry, is rapidly upskilling, and might be willing to bring their skills to our team.” When you do this right, the jobs come to you even if you are entry-level talent. 

#3 Gain Experience 

It can be real-world experience, it can be simulated experience, it can be volunteer experience, but you need to be able to go into your interviews and talk about what you’ve done.

#4 Unlock the Hidden Job Market

You need to know how to search for the jobs, how to identify the right ones to apply for, and, even better, you need to know how to unlock the hidden job market.

#5 Prepare for the Interview

Interview preparation is a critical skill set that no one teaches you. You need to know how to crush the interview.

These five steps effectively describe the gap between what employers are looking for and what entry-level talent in any industry need to present. The smaller the gap, the faster candidates are hired and the higher incomes they are offered. They translate to most industries, and at any point in your career, you will increase your success and income if you implement them. 

How to Choose a Career

When we were building TalentStacker, we wanted to figure out how we could provide the fastest, most in demand career training to help people break into a skill-based industry. Like we mentioned in point #1 above, there’s no shortage of options. But not all skill-based careers are created equal, so we used the following four criteria to narrow down which path would provide the best outcome.

#1 A Tech Career with a Clear Skill-Based Certificate Barrier of Entry 

Learning a coding language is often the biggest barrier into tech. It’s not easy, and for a lot of people, it can be extremely challenging. We knew whatever we chose shouldn’t require people to learn to code.

#2 A Huge Growth Curve and Massive Deficit of Talent

In economics, prices are determined by the law of supply and demand. Large demand with limited supply drives high prices. With this in mind, we surveyed the employment landscape to see which careers had a high number of job postings that sat vacant for weeks or months. That clued us into both the demand for that role and the supply of available candidates to fill it.

#3 High Starting Salary with Great Promotion and Raise Potential

Many people think of the adage “one step back, two steps forward” when they’re considering a career change. They think they’ll need to take a pay cut in the short term to clear the path for long term growth. That’s not what we were after. We wanted it all: a high starting salary and a clear path to six figures within 24 months.

#4 Remote Work and Full Benefits to Unlock Geo Arbitrage

The pandemic made remote work the norm, and one of the massive benefits of remote work is that is allows you to earn an income from a company headquartered in one city but live in another with a lower cost of living. This is called geo arbitrage, and it can help you bank a significantly larger portion of your income every month. In addition, remote work can help you design your life around your life goals, not your commute schedule.

After reviewing the job market through the lens of these four criteria, one skill-based career stood head and shoulders above the rest: Salesforce Administration. The 2022–2023 numbers for Salesforce administrator jobs reliably show an entry-level starting annual salary of $72,000–$74,000 with a clear path to six figures within 24 months, and an experienced Salesforce administrator with five or more years of experience can make $150,000–$170,000. You can break into the career without a technical degree, and +80% of the open positions are fully remote. All our boxes were checked.

What Is Salesforce?

Salesforce, at its core, is a software that helps companies manage their relationships with customers and potential customers. Salespeople use it to track their progress with a lead. Marketers use it to automate critical functions like emails, and customer service teams can use it to keep track of and prevent customer issues. (For a deeper dive, check out this post.)

This type of software is called customer relationship management software, or CRM for short. Almost every company you interact with uses some sort of CRM, and chances are, they’re probably using Salesforce. Salesforce is the #1 CRM in the world with a market share of 23.8%. Remember how we talked about supply and demand? Plus, the demand for Salesforce administrators has been trending upward for more than 10 years and is showing no signs of slowing.

What Is Salesforce Administration?

Salesforce is an incredibly powerful software, but it requires some configuring to meet each company’s individual needs. That’s where a Salesforce administrator comes in. Salesforce administrators work inside organizations (not for Salesforce the company) to help users get the most out of the Salesforce platform. They set up dashboards, create alerts, and automate critical business functions, all with zero coding.

You don’t need a specialized college degree or an extensive technical background to land a job as a Salesforce administrator. In fact, you don’t even have to take the TalentStacker program to get certified. Salesforce offers self-paced training through Salesforce Trailhead. But if you’ve ever tried to learn a language or musical instrument on your own, you know the massive benefit of structured learning.

That structure combined with the support of our community is what TalentStacker is about. Making a career change is hard. Making a career change alone—that can feel impossible.

If you want to find out more about a career in Salesforce administration, our free 5-Day Salesforce Challenge is the perfect place to start. It gives you all the information you need to determine whether this career path would be a good fit.

Supercharge Your Path to Wealth

JL shared with me that one piece of feedback he gets from readers of his book and blog is that a perceived obstacle to following the simple path is that it’s difficult to save 50% of your income on a low salary. It’s a great observation, but it assumes that your salary is static and there’s nothing you can do to increase it. But if you could double your income in under six months with a clear path to six figures, that unlocks options and gives you additional resources to follow the simple way to wealth so clearly laid out in this blog.

Over the past two years, we have proven this model definitively. More than 1,000 students from all walks of life have completed the program and landed jobs like clockwork, earning double or even triple their old salaries, and January 2023 was our biggest hiring month yet! These results happened against the backdrop of a looming recession and a wave of tech layoffs because the demand for this skill set is so high, and individuals with our training are simply the most highly qualified entry-level talent in the world. 

To put it lightly, I believe in this program. I have two brothers who are currently going through the training program, and my business partner’s two sons have both landed remote jobs through this training. I talk about it constantly with friends and family because I know how life-changing it is. I would consider it a disservice to those around me not to share it. Between career skill training and financial independence, I believe we have uncovered the two biggest life hacks for the modern worker.

If anything Shawn or I have shared in this post resonated with you, give the 5-Day Salesforce Challenge a shot. It’s free, it’s self-paced, and it may dramatically change your life and supercharge your path to FI.

Click here to learn more about Talent Stacker, or here to read The Simple Path to a Lucrative Career, a related post by JL and ChooseFI CEO Ed Tee.

About TalentStacker

Talent Stacker has helped +1,000 individuals jump-start their Salesforce careers. With over $40M in salaries in 2022 alone and an average income of over $73,000 for our members in an average time of fewer than five months! Find out why the program is so unique and consistently helps students launch their Salesforce careers, get in front of hiring managers and recruiters to showcase their value, and land the job. Click here to learn more.

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