Sales to Financial Independence: Interview #1

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One of the underlooked paths to Financial Independence is a career in professional sales.  This interview series is meant to highlight those who’ve achieved financial independence or are on the path to financial independence through a sales-related role.

Our first interview is with 2B1S.   He has an interesting story about navigating his way into sales and the freedom and flexibility this afforded him.

Please tell us a little bit about yourself:  How did you find financial independence and where are you on the path? 

After a semi-successful attempt at college, I ended up in a retail job. A couple of years and accompanying promotions later, I found myself standing in my own store thinking, “is this it”?

It was then and there that I pulled out my smartphone and searched “how to retire early”. Down the rabbit hole I went……since mid-January was a slow time in retail, I found myself with a lot of downtime to read blog posts, articles, peruse forums, and consume as much content on how to not have to work 40+ years in uninspiring jobs. A few short weeks had gone by, and I finally stumbled upon Mr. Money Mustache’s The Shockingly Simple Math Behind Early Retirement post

Which at the time felt like it was written for me! The timing couldn’t have been better, and the idea of retiring in 15-20 years instead of 40+ was my gateway drug into the world of FIRE. There were new ideas and non-mainstream folks writing blogs about extremely early retirement. The so-called “super savers” dubbed by CNBC who were able to save half their income, sometimes even more, and retire in their 30’s. This sounded great, except for the fact that I was making a measly salary with some commission thrown into the mix, and saving 50% of my income would mean living below the federal poverty line. I realized that in order to really accelerate my path to FIRE, I needed to come up with ways to increase my income. A decade later we find ourselves almost financially independent, which has already created many options for how/when we want to work. 

Views from a sales funded career break

What was your introduction into sales?

Looking back now, whether you like it or not, you’re selling throughout your entire life. From selling ideas and negotiating with parents, teachers, friends in childhood, to selling yourself to potential colleges and employers in adolescence. Everyone needs to be able to sell, regardless of their chosen profession. Certain people discover that they enjoy it and are good at it, and oftentimes are drawn to jobs and careers that allow them to leverage this skillset. I was always a contrarian in my childhood and questioned everything. This resulted in many debates with authority figures, employers, and eventually customers. 

Long story short, my first exposure to sales was working the cash register in high school, followed by my stint in retail after dropping out of college (I did say it was a semi-successful attempt ;)). I learned formal education wasn’t for me, but I did get plenty of practice selling. 

Were you hesitant to get into sales?   Why?   What helped you overcome it?

I landed in sales by sheer luck, if you believe in that sort of thing. Getting a job in retail forced me to learn how to cold approach customers, which was uncomfortable at first. It was a fairly aggressive industry where the interaction with the customer could greatly impact the outcome of their visit to the store. It was also the first time I had the opportunity to earn “commission”. Very quickly I was addicted to turning my minimum wage base pay into $20+/hr, which felt like a ton of money over a decade ago. After a while, the “selling” became so natural and enjoyable that it was effortless. I realized that through a combination of being interested in what it was that I sold, caring about the customer, and having the ability to solve their problem created a win-win situation and my income scaled accordingly. 

What helped you the most when it came to being a salesperson?

Realizing that it’s not about you. The best salespeople are authentic, both to themselves, and to their customers. In the retail world, I was helping people improve their lives through the knowledge I shared and accompanying products and services that I sold. Learning to understand the needs of the customer and then being able to gain their trust that those needs were my priority served me very well later on in my career. Hint: I didn’t stick around in retail forever.

After spending several years in retail management, taking on increased responsibility,  I realized that the income wouldn’t cut it if I wanted to get out of the rat race before the age of 50. An interesting opportunity presented itself when an old friend from college reached out about a job at his employer doing entry level sales in a business-to-business setting. I applied, and despite having no college degree or relevant experience, sold myself to the company as someone who, with the right training, would become an asset.

Tell us more about your sales job(s):  What were you selling?    How much was account management vs. new business?  How did you get new customer leads? 

The new gig was in the technology space, and it was a whole new world. I was now selling software to commercial customers. It required learning the technology itself, a whole entire nomenclature used by the tech industry, and slowly but surely about the customers themselves. Specifically their needs, problems, and how to solve them with technology. It was a fifty-fifty split of managing existing accounts and finding new business. Compared to the world I had come from, the stakes were much higher. Getting leads was a luxury, as the job involved a lot of research and coming up with my own prospecting plans. Identifying target companies, decision makers within those companies, digging up financial reports, shareholder meeting notes, reading the news to learn about business challenges, and what would resonate with prospects. The juice was worth the squeeze, as “new logos” were rewarded with handsome compensation and upward mobility within the company. 

What did you see this do for your income? What were some of the other benefits and/or drawbacks of a sales job? 

After the first full year of learning the ins and outs of this new world, I saw my income more or less double. There was no ceiling to earnings, within reason. It felt surreal to learn how much professional salespeople could make. There were more senior sales roles than mine, which had average earnings of double what I was now earning. This was motivation to do well, beyond just the short term paycheck. Afterall, MMM’s shockingly simple math behind early retirement was all based on savings rate. If spending could be kept the same, and income could double or triple, it would potentially shave decades off the path to financial independence. 

Some other benefits of a professional sales job are seen only with good employers that invest in their people. In the first few years of my professional sales career I was lucky to get a ton of training that helped with personal and professional development. It was like getting paid to get a crash course MBA from the school of hardknocks. You learn a lot of portable skills that transfer well to other careers if you decide sales is no longer something you want to continue with. Another benefit is employability. Every organization needs salespeople. Whether it’s a corporation in private industry or a non-profit asking donors for money, the skills you hone as a professional salesperson mean that you will always be in demand, so long as you are halfway decent at it. 

The two biggest drawbacks I personally experienced were imposter syndrome and burnout. The former was something that I experienced over the first few years of my new career in tech sales. The higher I climbed the ladder, and the bigger my paychecks got, the more surreal it felt. I often worried that someone would figure out that I was faking it till I was making it, except I was making it! Regardless, those feelings resulted in quite a bit of stress and self induced pressure. Then a stint with a less than ideal employer left me with some pretty severe burnout. Sales takes many shapes and forms, but one universal expectation at the highest levels is that salespeople need to always be “on”. This means that you end up sacrificing a lot of your personal life in order to make deals happen, whether that means extensive travel, late nights, canceled plans, etc……it all has an impact both physically and mentally. 

Salespeople are often portrayed as extroverted type-A personalities:  Is that you?  If not, what advice would you give someone who does not fit that mold?

When I was younger, I would have pegged myself as an extrovert, and my wife will tell you that I’m very much type-A. The truth is, I’m more of a “social introvert” and once I realized that, it was a game changer in how I approached my life and career. 

To the readers who are not extroverted type-A’s, don’t worry! The most successful sales people I have encountered in my career are the ones that leverage their ecosystem and pull the right people in at the right time. They are the ones that take the time to understand the problem, empathize, and think beyond the surface to provide solutions that are effective and strategic. Professional sales these days is not what you might remember from movies like “Glengarry Glen Ross”. Sure there is a social element to sales, and being an excellent communicator is extremely important, but you don’t need to be extroverted or type-A to master these skills. 

Were you tempted to spend more money as you earned more?   What helped curb that?

The temptation was certainly there and some lifestyle creep was unavoidable, but luckily I discovered the FIRE movement before the sudden jump in income. This forced me to look at this extra money as a tool to be used to buy my freedom. The first few years of earning more money did result in buying a luxury sports car (albeit used and already depreciated 50%), moving into a slightly larger apartment, and increasing spending on things like restaurants and experiences. The kicker was that I was still able to save more than half of my net income, so by mainstream standards quite frugal. Over those years, increased spending had diminishing returns on happiness, and after a while too much “stuff” filled my life. My wife (fiance at the time) and I realized that being waited on at restaurants lost its appeal after we got better at cooking and baking. We also realized that most of our favorite hobbies and activities cost nearly nothing. We doubled down on being active and outdoors, started downsizing our possessions and embraced minimalism. This supercharged our savings rate, and thus reduced our time to FI. 

If you could change careers today, would you stay in sales or do something different?

I would stay in some sort of sales/business development role, but possibly change industries. Tech is cool and it’s treated me very well, but it involves way too much time indoors and in front of a computer screen. I’m at the point where I would love to take the skills I have developed over the past decade and apply them to something that would have me outside and active. One of my motivators to reach full FI is to be able to focus on projects and activities for the sake of building something awesome, with income being a byproduct. Many FIRE bloggers and early retirees end up with a “second act”, I just don’t know what mine will be yet. Figuring that out sounds like a great way to spend a few years after pulling the plug from the corporate world. 

What advice would you have for someone considering this for a career on their path to financial independence?

If you think you might enjoy it, I would give it an honest try! Selecting the right industry, organization, and type of sales role can be crucial to both enjoyment and success. It’s a career that will definitely grow you as a person, force you to learn many new things, and constantly push you outside of your comfort zone. So long as you’re ok with some pressure and rejection, it can be extremely rewarding. There’s also something to be said about being able to positively impact your organization’s bottom line directly. High level business to business sales people have a very high income potential. The top 25% of professional sales people will earn similar incomes to doctors, lawyers, software engineers etc. Same goes for different types of sales such as commercial real estate, financial sales, boat/yacht sales, etc. So long as you put in the time and effort, it’s one of the easiest paths to becoming a high earner without having to invest the time and money into extensive schooling. 

Another benefit of a sales career is the flexibility of employment. It’s one of the few professions that doesn’t require much in the way of continuing education, accreditation, or continuity within a specific industry or field. This means that once you reach a certain level of assets that gives you some confidence, you can experiment with intermittent employment, as well as negotiating better terms of future employment. I was only three years into my professional sales career when I started leveraging this new found freedom to take longer than normal breaks between different roles. After several more years, between a growing pile of FU$ and with the confidence that I can always find another job, I took a year long sabbatical! Returning to the professional world after a year off was not difficult at all. That year also proved to be an amazing test run of FIRE’d life. I came back to work recharged and ready for what was next. Now I’m looking towards next year or two to do it all again……except this time I may never return to full time employment. 

How would you take the skills you learned as a salesperson and apply them to other areas of FIRE?

There are so many ways to apply this broad skillset……the biggest one would be interpersonal skills. Sales teaches you to leverage your human capital, solve problems creatively, and be able to communicate well with others. Financial and business acumen are both important in professional sales, so entrepreneurship may come more easily to you. Reading and understanding contracts and legal documents can also be a very good life skill to have, as oftentimes the devil is in the details. If you’re a truly talented salesperson, then you’ve also likely developed your emotional intelligence, empathy, and are able to navigate difficult situations with gusto. 

Last but not least, being a salesperson means you can always help someone with a good idea/product/service increase revenue and earn a living, if the RE part of FIRE doesn’t play out the way you had planned or hoped. 

Key Takeaways:

  1. Sell something that is expensive.   The interviewee went into enterprise software sales and quickly saw his income double from his previous job.   He also saw that professional salespeople with the right company/product suite can earn pay equivalent to traditional highly paid/highly educated professionals.   This is a career path that directly rewards effort.
  1. You don’t have to be a social extrovert to master sales.  The higher end jobs are a combination of relationship building, analytics, and problem solving.  Most importantly, sales jobs require listening.  I’ve seen people so extroverted they are unable to listen to a prospect or customer
  1. The urge for lifestyle creep is real.  The interviewee had the good fortune of discovering Mr. Money Mustache and developing frugal habits before having the firehose of cash unloaded on him through the new job.  

If you enjoyed this interview, please leave a comment below.   If you are in sales or retired from sales and want to contribute to this series, please reach out.

3 Replies to “Sales to Financial Independence: Interview #1”

  1. There are some references to type-A personalities in one of the responses. What personality ‘system’ is this referring to, and/or what are the other personalities?

  2. Agreed on selling something expensive. I went into commercial real estate sales. I cannot imagine being a super salesman for say Best Buy. Hard work and limited upside. Great article.

    1. Believe it or not, a good friend of mine in college worked in the home theatre department at Best Buy and made 6 figures per year for 3 of the 4 years he was there (commission based), while securing his engineering degree from a state university. If you enjoy what you do and you’re good at it, there is money to be made almost anywhere.

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