How To Get A Raise: The Less Traveled Path To Financial Independence

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Remember how I said in this post that nothing makes me happier than when people work towards FI, follow their passions, and create happiness in this world?

Well, today, I’m pumped to introduce you to Chautauquan Brandon, who did exactly that. When Brandon first came to Chautauqua UK last year, not only did he impressed us with this kickass video editing skills, he elevated the whole experience with loads of laughter (mostly my childish giggles). Case in point: we were eating an English dessert called “Spotted Dick” and Brandon went around the dinner tables snapping “Dick pics”:

The description says it all

So you can see why we’re kindred spirits. I was ecstatic when Brandon came back to Chautauqua this year, bringing along his lovely girlfriend, Kimmy (you can see a video on her thoughts about Chautauqua here). And I knew, from the first time we met, that Brandon was a go-getter, but what completely blew me away was his salary increase since the last time we chatted. I knew this was a story that needs to be shared. So without further ado, here’s Brandon’s story about going from working in factory making $7.50/ hour to a 6-figure job that takes him all over the world:

How To Get A Raise: The Less Traveled Path To Financial Independence

By Brandon

A few weeks ago I was at Chautauqua where FIRECracker and Wanderer were kind enough to sit down with me after hours to review my finances. Yes, these are the fun activities we stay up late for at Chautauqua. I started by showing them my costs and savings rate. Then FIRECracker’s eyes focused on my income and gasped, “You make how much?! A year?! Wasn’t it like way less the last time we talked?” It was.

I definitely don’t take my high paying career for granted based on where I’ve come from. Although I hadn’t realized how unusual it was to double my salary over the course of 5 years. It got me thinking about my much less talked about path towards Financial Independence. Getting paid! Specifically getting paid more for the work I’m already doing.

My job as a Digital Consultant (somebody who helps companies build software to solve business problems) takes me all over the world. Currently I’m writing this with my laptop sitting on a tray table flying back home from Silicon Valley. I just finished a week of meetings with one of my biggest clients and even got a preview of some top secret technology that hasn’t been released to the public yet. Not only do I get to work with the biggest household names in the tech industry, but I’m paid bank to do it. If you had told my 17 year old self I’d be making six figures and flying all over the world to solve technical problems I would have blown smoke in your face and walked away.

Get out of here with that mess bro…

Small Town, Limited Opportunities

To give you an idea of how I got my hefty salary and how you can too, let me back up a bit and tell you about my home town….It was so small that there were only 63 students in my graduating class. Have you heard of a “One Stoplight” town? Well, we didn’t even have that. One restaurant, one bank, one cop car, you get the picture… In a tiny town like that the best job I could get was a factory job in the auto industry because college was something that other people did.

Right out of high school I landed a manufacturing job in, you guessed it, the auto industry. It was the only option I thought I had. It wasn’t all bad though. Factory work bought me a house, car, and 2.4 children. Well not quite…nobody wanted to sleep with me so I spent that portion of my salary on cigarettes and beer.

Working on a factory floor isn’t what it used to be. My grandfather worked at Ford Motor Company with a starting salary of $15.72/hr (adjusted for inflation) in 1957. Then retired after 25 years with a full pension. Whereas my first job started at $7.50/hr with no pension. After 12 years I was making $21.25/hr because I averaged $1/hr annual raises.

At the age of 30 I decided to make a career change from factory work to knowledge work. And it paid off. Let’s take a look at my salary over the past 19 years.

This is the first time I’ve looked at my salary in a graph. What stands out to me the most is the power of education. That huge dip around 2012 and the skyrocketing line afterward is when I went back to school to finish my degree in International Business and Management Information Systems–the first in my family to do so.

I worked harder in college than I ever had in my life and six months before graduation I accepted an offer from the largest privately held company in the world. I had no experience in technology, outside of helping my mom log onto Facebook, yet my starting salary was significantly higher than my factory pay.

Discovering FIRE

Thankfully I discovered FIRE (shoutout to GoCurryCracker) shortly after my salary started increasing exponentially. Otherwise I’d still be spending my extra income on cigarettes and beer instead of making it work for me. As I devoured the various FIRE blogs I noticed that people concentrated on two main paths to get there.

  1. Cutting costs by eating lentils and sharing a bathroom with stinky roommates
  2. Earning extra money from a side hustle like real estate or some type of lifestyle business.

Nobody seems to concentrate on increasing their salary as a means to get there. Maybe it’s because a lot of people pursuing FIRE hate their jobs. For people like me who love their jobs though I feel like it’s a perfectly valid path. I can hear the haters now, sure, sure you love your job. Would I do it for free? No. Would I continue to work after FIRE? Maybe, maybe not. I’m looking forward to having the option.


A year and a half into my Digital Consulting career something unexpected happened. I was laid off with the other 80% of my department in 2015. Shit. No job = no salary.

When I finally found a new job, to my surprise, it came with another raise. As you can see from the chart from 2015-2018 I continued to have significant raises. My salary is just over $100,000 which is the number that made FIRECracker gasp in disbelief. “You have to write a post on this. People have to know!” She said.

It seems there are only two places where talking about salary is not taboo. Chautauqua and blogs. It’s a taboo subject and there’s no way around it. I wish it weren’t though. I’m proud of my raises and I want to share my story so you can get paid too! My purpose for sharing my story is two fold. To shine some light on a less talked about path to FIRE and to show you how I did it so you can do it too. You have more earning potential than you think but you have to take some risks to unlock it.

What I’ve learned about getting paid

Each of my 6 raises after college came from a different managers. It worked to my advantage because I think managers take their employees for granted. They get familiar with you and when you’re badass they come to expect that from you. So it doesn’t seem like a big deal to them when you go over and above. That’s when you have to make a decision to stay or go because you’re manager is not giving you the recognition you deserve.

Your manager only has so much authority. Even if they wanted to pay you more, it’s not their money. They are likely working within a budget or some other type of company constraint. The work you’re doing might be worth a 20% raise but they might only have authority to give you 5%.

Raises are given in context of everybody in your company. When I got the biggest raise of my career my manager went to bat for me and she had to sacrifice giving raises to her other employees to do it. Keep this in mind too, every employee thinks they should be making more. Every single one. You, me, and that incompetent bum that comes in late every day. Managers have to balance all those expectations.

One of the hardest truths about compensation is that it’s not linked to performance. Let that sink in for a minute. Salary and performance are not related. We are programed to think that if we work harder we will get paid more. My experience has shown me that is not true. Case in point, you probably know some idiot that makes a ton more that you. A boss, owner, etc… and you ask yourself “How the hell did they get in that position?”

If you want a fat raise and you’re manager can’t or won’t give it to you then you have to change managers. That means finding a new job. “But I’m comfortable at my job and I like the people I work with.” Okay that’s awesome. Just know that you are sacrificing your fat raise for them.

But Wait There’s More…

There’s an opportunity to increase your salary no matter your situation. Quitting my job and going back to school was one of the most challenging things I’ve ever done. There were some days that I was so scared of failing that I didn’t even go to class. Counter intuitive I know but that’s what anxiety does to you.

I love the phrase “You’re stronger than you think.” We have so much potential inside us but we’re so scared to pursue it because we might fail. I’m not going to tell you I’m not afraid of failure. I am. But looking at the potential I’ve been able to unlock up to this point assures me that I have to take those big risks in order to get paid.

My path towards FI is a less traditional one. I’m not counting every penny or using my extra time for a side hustle. Instead, I’m pushing hard, taking risks and so far I’ve been able to double my salary. Now, I’m sharing my story with you so you can do it too. What’s my compensation for sharing my story? Some crappy Greek wine that Wanderer shared with me while we watched the moon reflect off the Aegean Sea. Ahh well, it’s better than a swift kick in the face with a golf shoe.

Have you ever had to negotiate a raise? Did you get what you wanted? If not, what did you do about it?

What are your ideas for getting paid what you deserve?

Note: To learn out more about Brandon, check out his blog “Today, I Learned About Myself”

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67 thoughts on “How To Get A Raise: The Less Traveled Path To Financial Independence”

    1. I think you have to find a manager that is able and willing to pay you what you’re worth. What you’re worth is your value to the company and education can help increase that value.

      Hope that helps!

  1. Thanks so much for sharing your story Brandon! I’m completely with you. A big reason I was able to cut my time to FIRE in half is because I almost doubled my salary in a few years. I did this with job hopping after negotiation didn’t work. It’s wild to me that you can convince a stranger in an hour interview to give you a lot more money when your current boss who sees you kicking ass every day won’t. I think you hit the nail on the head for why that is though so thanks for clearing up that mystery!

    1. Nice work, APL! This is the path that many of my friends are currently taking–getting a higher salaries after job hopping. You never know how much you’re worth until there’s another company wanting to throw money at you!

  2. What an inspirational story…well done. Your point about the limitation of managers to give out raises is an important one. I was a senior executive (prior to retiring) and oversaw a large group. One employee in particular was fantastic but the raise pool to compensate her was small (total 3% of salaries to be shared among ALL staff). She got an offer from a head hunter that was 20% higher than her present salary. Thank God she loved working for me so she came to me with the offer before accepting it. I went to HR and told them that we were giving her a 30% raise because we could not afford to lose her. What a fight I had…but we kept her…and she was an even better employee after because she knew how much I valued her contribution and that I was willing to go to bat for her. Employers DO know who is going above and beyond and when the sh!t hits the fan…they know who they want to keep. You my friend, sound like one of the keepers!

    1. Great story! Exactly what I have found. You my friend sound like one of the good managers that is willing to go to bat for your employees. Too bad you’re retired otherwise you might be getting a call from me…

    2. Wow, way to go to bat for your employee ObW! I can totally see why she was a better employee after since she knew she was valued. I wish I had a boss like you! In one of my previous jobs, my boss tried to keep our team lead, but couldn’t match the offer another company gave her so she left. It’s good to know your worth!

  3. Thanks for sharing Brandon’s story! When you consider he lives in a small town and makes that kind of money, he’s really killing it!

    Most people have to live in the big city to earn a salary like that!

    Congrats Brandon!

    1. Ah, I should make a clarification then. I had to move to a larger city to go to college and out of state for Digital Consulting. Completely worth the move though.

  4. This is not correlated to the post but I have a big question. I’m fully invested (2 million) in a 30-Year Treasury bond I bought a long time ago at 5.25%. Do you guys think it’s time to start putting some of that in equities or is it still too early?

  5. Yes, raising your salary is another option to reach FIRE faster. But in my opinion, it is the most difficult starting path to FI when compared to cutting spending and entrepreneurship. The reason is the high risk:reward ratio.

    To list off some overly simplified examples:
    Going for more education = debt
    Asking for a raise = may compromise job security or job reputation
    Job Hopping = risk of office reputation and strength as a future job candidate

    The FIRE community is selectively risk averse, but they are especially averse to risking their main source of income while pursing FI.

    It is easier and less risky to decrease your spending or develop a second stream of income from a hobby you enjoy, until you are financially stable enough to take larger risks. It is easier to go for a higher salary when you have a cash flow positive gap between your income and spending, and emergency savings. So when you do ask for a raise or look for another job, you have a buffer if shit hits the fan. That is why you see a majority of blogs based on saving money and/or touting money making side jobs.

    I applaud you for going the risky route and pursuing salary increase first, Brandon! Just thought I’d give another point of view about why we don’t hear about your path more often.

    1. For sure, it can be more difficult since you have to rely on others to make it happen. But with cutting costs at least, you can only cut so much. I would argue that salary can go up farther than costs can go down.

      Let me add a little bit to my story. I DID take on about $40,000 in debt to get my degree. However, since my salary was so much greater, I was able to pay it off in less than four years. You can see by the graph how immediately and sharply. Also, I don’t think I would want to work for a company where asking for a raise “may compromise job security or job reputation.” And employee loyalty is dead unfortunately. It’s pretty unusual that I review a resume where a candidate has worked for a single company for more than 3 years. I’d rather have an badass employee for 3 years than an average employee for 10.

      1. I agree that there is a rock bottom limit for spending and salary can, theoretically, have no limit.

        I think that is why people control their spending first. Once you find your rock bottom, you can tailor your income to fit whatever FIRE window you want. (Ex: “My after tax income is currently 2x my spending, and at this rate I can retire in 15+/- years. If I find a job that offers me an income 4x my spending, I can reduce my working career by half.”)

        I agree that people don’t want to work for a company that may compromise your job security or growth if you ask for a raise, but sometimes you don’t know they’re that type of company until later. It happened to me. Thought a company was great until I was blindsided by an odd circumstance. Point I’m trying to say is this: Asking for a raise is hard no matter what situation because of all the variables. And I completely understand when people go with the cut-spending route over the pursue-high-salary route.

        I don’t think employee loyalty is dead, it just depends on the profession. HR people in my field and geographical area value loyalty. I was in my two previous jobs for over three years, and I know I was a favored candidate for a couple positions because of my loyalty.

        I think your industry, the tech industry, it is a bit different. There is a lot of evolution in technology in general. So turnover in ideas, education, employers, and employees is more common than in other fields.

        1. I mean, there is always the awesome combination of increase salary, cut spending, and rock a side hustle? amirite?

          Definitely feel you on the industry specifics.

        2. Thanks for your 2 cents, MSB! I agree that it’s different in the tech industry where you need to upgrade your skills constantly and turnover is high–interesting to see how it works in the other industries.

  6. Brandon, it was awesome to meet you and Kimmy in Greece. Having spoken with you, it is no surprise that you’ve had such a steep trajectory in your career earnings. I love your writing and will continue to follow your blog. Keep up the great work and thank you again for all your help in Greece.

    Cuando vienes a visitarnos en Africa?

  7. An alternate route is to get increases out of fear. If you are so irreplaceable that they will pay almost anything to keep you. I maintained that status my entire career with a single company from summer intern to GM and VP of the division. My starting pay as an engineer increased by 2400% over my career because I got a lot of job offers from the competition but never took them. However I always shared them with my bosses at the time. It not only gets the raises but saves you ever having to incur the costs of moving or rebuilding your reputation elsewhere. The only problem is that this only works where you are a recognized savant at your job and where your job is tightly aligned with company profits.

    1. Excellent point. Just to “math this shit up” I’d be making $180/hr or $374,400/yr if I was on your trajectory.

      I’m going to cut this reply short, I got some more work to do…

      1. I’m not world class but I had a lot of talent and I picked that job out of many offers because there was little competition and that made me look world class by comparison to my competition at that location.

    2. “My starting pay as an engineer increased by 2400%…”

      Wow! What type of engineer are you if you don’t mind me asking?

      1. Chemical engineer, and I had a long career with some of it in periods of high inflation so even though I did well inflation makes it look better than it would now. I wouldn’t have had that percent increase in times like now with low inflation.

  8. I’d suggest a further slight variation on Brandon’s path to FI.

    The logical extension of hunting pay increases through job-hopping and proactively negotiating salary raises is to quit the arena of permanent full-time employment altogether and become an independent contractor/consultant It’s not as hard or risky as people imagine, once you build a solid in-demand skill set, and is so much better than being an employee!

    I come from the same world as FIRECracker: that of IT for big banks in Toronto.

    I started out working full time as a business systems analyst with one of the big five Canadian banks. I was frustrated with a relatively low salary and dismal prospects of increasing it, but I never had the talent of someone like Brandon to negotiate raises.

    Instead I fell (quite by chance, I admit!) into the wonderful world of contracting.
    One day, nearly six years ago, I was contacted by a recruiter on LinkedIn, who was offering a 6 month contract paying about 50% more than what I made doing the same work as an employee. I took it and never looked back.

    Five contracts later, I am now making an income about 2.5 times the size of my old salary.

    I could have easily had fewer contracts, and stayed longer at each one, since the programs I worked on all lasted at least two years if not more. But I was very keen to both diversify my skill set and grow my pay rate, so I hopped as frequently as possible.

    Which is not a problem at all for a contractor. Unlike the world of employees where “Job Hopping = risk of office reputation and strength as a future job candidate”, things are completely different. Leaving after 12-18 months to take advantage of a better-paying opportunity is completely normal here and not frowned upon. Everyone’s cool with it, because that’s more or less what contractors are expected to do.

    For a contractor, frequent hopping = more gigs = higher pay on each new gig = more marketable skill set = better ability to sustainably get high-paying gigs in the long term.

    My story is not rare or exceptional either. There are hundreds of mercenary people like me on every major program or project in Toronto.

    At work, I currently sit in a room with a dozen other contractors like myself.
    All are in their thirties and are making comfortable six digit incomes, about twice what they would have made as employees.

    In fact, they are making roughly equivalent of full-timer salary for a manager or director, but without any of the stress of a managerial job.

    Of course, yes, there is a certain amount of stress and risk involved in stepping out of your comfort zone, abandoning full time employment and facing the need to hunt for work every year, when you first enter contracting. Takes some guts to do it the very first time.
    But within a few gigs you get used to it and it becomes routine. When I think about how much energy folks spend chasing raises and promotions in traditional, corporate-ladder-climbing career paths, I don’t feel like mine is a very risky or stressful path at all…

    Sadly, most of my fellow mercenaries use their increased incomes to buy bigger houses.
    But it definitely can be a pretty good path to FI.

    So if you are in a similar situation of having a decent mixed technical-and-business skill set and struggling to get the salary it deserves, start sniffing the wind: bring your LinkedIn profile up to date, connect/chat with recruiters and network with current and former colleagues. You never know: there could be a lucrative contract market for what you do out there, which you are just a few steps away from claiming…

    1. hedgehog, love this story! “2.5 times the size of my old salary” – another person that has doubled their salary or more by taking some risks.

      I’ll likely be heading down the contracting path shortly. Just getting a few more years of experience under my belt before I take that risk.

      Thanks for sharing!

    2. “quit the arena of permanent full-time employment altogether and become an independent contractor/consultant.”

      This is a really good point, hedgehog. Some of my friends have done exactly this and increased their salaries by 2-3X. Sure, they lose out on benefits, but the increased salary and flexibility is worth it. The “security” of a full-time job is an illusion these days anyway. I would say the contracting + partial FI or FU money is a good combo, since the FU money keeps you from worrying about not finding a contract right away and lets you take you take time off between contracts.

      Thanks for sharing!

  9. Brandon, was there something that made you take that critical risk of going back to school? Did you go to school part-time while still working? How did you manage living expenses during this time? What’s inspiring about your story is that you took a risk later in life to get an education and invest in yourself despite the environment you grew up in and the factory work you started with. This took courage. How did you find that courage? Thanks both Brandon and Millennial Revolution for sharing this story.

    1. Oh PurpleSquirrel my friend, what a deep question. Let me address the expenses question first. To cover expenses I took out student loans and cashed out a small profit sharing account I had with the company (something like $30,000). I ended up with about $40,000 in student loans at graduation but was able to pay them off within 4 years since my income increased so dramatically.

      Now for the question of “How did I get out?” Most of the people from my town are still there stuck in the poverty loop. Where did I get the courage? What triggered me taking on such a large risk? I can’t really say. I just always knew in the back of my head that I wanted to be more and that education was something that was important. I wish I had an “aha” moment to share but there really wasn’t a single moment.

      However, I did have tons of mentors along the way. That would take a whole series of posts to thank all of those wonderful people. Maybe I’ll write a follow-up on my blog. Thanks for the idea.

      1. I second that a great idea! Send me the link for your follow-up post(s) when you’re done, Brandon, and I’ll link it to this one.

  10. The great thing about personal finance is there are so many angles to play with. Find what works best for you.

    For me, that included discovering I was resilient and almost doubling my salary. That is after 3 close family members dying, break of an 18 year relationship, and a lay off. After almost every aspect of my life had been burned up in smoke, deciding “fuck it, let’s take a risk and try working contracts to increase income” may have been a little scary but didn’t seem so crazy.

    Two years before that though, I would definitely have concentrated only on reducing expenses. So yea, it’s all about what works for you, and you never know, it can change with time. You take a little risk, notice its not so scary. So you take another…

    1. Heck yes, get some! So happy you could take such a rough situation and come through stronger.

      Also, so many stories of “doubling” salaries. So badass! Congratulations!

  11. So glad you shared your story, Brandon, and HIGH FIVE! In my experience (in Big Pharm), one of the best, and sometimes only, ways to get a raise is to switch departments or companies – for all of the reasons you mentioned (managers only have so much control, etc.).

    Loved this line: “There were some days that I was so scared of failing that I didn’t even go to class.” …I can’t relate at all. Nope.

    1. “sometimes only, ways to get a raise is to switch departments” – my first job out of college actual taught this as a way for advancement. They said that career advancement was more like a “lattice” because you had to sometimes make lateral moves in order to make vertical moves.

      *high five* back at ya!

  12. Ambition, passion, desire, true grit… Is what shines from this story. My story is exactly the same as this, small logging town in Northern BC, no ambition out of High School. Worked in a shitty job and swore I would never go back to it ever again…

    College, one shitty job after another, yadda yadda yadda, but kept moving up the food chain. Training in IT, certifications, self taught… one day I will tell my story too.

    1. Yes, yes, yes “swore I would never go back to it ever again” – and neither will I. So awesome that you broke out. I look forward to hearing your story.

  13. Brandon!! I totally love this . You made me laugh out loud so many times, and if I weren’t ready to pull the RE trigger in a few months, maybe I’d get out there and find a higher paying job. 😉 In all seriousness, you are a real go-getter. I’m so glad we got to hang out with you and Kimmy at Chautauqua. Time for a reunion!

  14. Hi,

    I totally agree that it requires some risk-taking to get the raise. The traditional way of working hard in the hope of securing the raise at the present employer is now useless in to day’s corporate world context. This is evident in my current workplace in which I stayed for almost three years (come March 2019). I got less than 5% increment as compared to the remuneration which I got in March 2016 (when I joined on-board). I got 20% increment when I joined aboard the current organisation from the previous firm.

    The above goes to show that it does not pay to be a loyal employee. Take charge personally, is the way to go.

    My two cents worth of views.

  15. 1. Read the book “Never Split The Difference”. It will tell you how to negotiate and win.
    2. The best way to get a raise is either go to a new company or negotiate with your current company after being offered a position with another company. I have seen new hires make a higher salary than current employees in the same position.

    1. Hi Charlotte,

      I am not inclined to negotiate with the current company after being offered a position with the other company. It’s better to start afresh with the new company, taking into consideration the remuneration increment coupled with the move.


      1. Good point. Usually it’s more than just the salary that is making you look for a new job. Do what is best for you!

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