Quitting Up: How to Multiply Your Paycheck

When I look back at my career, there has been a strategy I’ve been running for years now to multiply my paycheck – I call it Quitting Up. Has this worked for me? I currently make 2.71X what I started out making when I began working and it’s not impossible for you to do the same. I’m on track, assuming my interviews go well over the next 6 months, to increase that to 4.3X my initial salary. How did I do this?

This strategy isn’t going to work for everyone. By the end of this article, you’ll understand that some of the barriers to having good employers and the ability to perform the leveling-up steps associated with Quitting Up may not exist in your field. Don’t let this just be mental. You’ll need to do research to understand how to make opportunities possible for yourself in your industry.

Quitting up requires the quick building of marketable skills and experiences to advance in your career as fast as possible. So you need to be prepared to put you back into it and start hustling.

Buyer Beware: What I’ll go on to describe in this article is either for the ruthlessly ambitious, the exceptional employee or the fool.

How does this strategy work?

Employers tend to value two things in resume reviews, experience and skillset. That’s it. There are some people who need soft skills to succeed, for instance in sales, but across most fields experience and skillset rule the day.

What we need to do to make our strategy work is first and foremost – get as much experience and skills as possible. We’ll cover the tactics of this below in later sections.

Experience and skillset are critical to each layer of the Quitting Up strategy. Without advancing either one of these as you progress through your career, you’re going to stagnate in this approach. You need to be aggressive and objective about what matters in your field and get those skillsets and experiences to make more money from your employer.

The strategy works as follows:

  • Maintain your current job and immediately begin seeking advances in skillsets and experience that is of value to the market*
  • Once you obtain an advancement of skillsets or experience in your field apply like crazy for every job that you have any of those skills for that will be a step up in your career
  • Once you land an reasonable offer** for a job a level above yours you need accept the offer and quit your job for the position.
  • In your new role, you need to start the process all over again

That’s it. Do this as much as you possibly can. I don’t care if your industry says you need 5 or 10 years doing something before you move up. You need to focus on the first step and the first step only, building your skillset and experience no matter what.

What qualifies you for the next time to quit up?

*How do I know what’s valuable in my domain or market? We touched on the need to make sure your skillet and experiences are marketable and now it’s time for the high-level of how to do your homework. No matter where you are in your career or field, finding out what is next is generally nice to know. So get going on this by pursuing the following, and don’t worry it is real homework:

Look for job postings, for your current job title, and just writing down what skills or experience ir required from each posting. Do this with at least 10 job listings. Do this in markets close to you for at least 5 listings and then find the industry leading companies and their job postings for 5 more companies.

Additionally, go to contractor listing sites like Upwork, Angies List/HomeAdvisor, and other sites directly related to your industry and search through job postings related to your existing skillset or expertise. Build another list from 10 postings

Once you’ve generated a list of what companies directly want from employees and what they want from contractors, you understand what the market is currently valuing in your industry. You also have a list of things that you probably don’t have experience in.

Those are your phase 1 skills.

The next set of skills that you need to look up using the same process as above for roles that are above your current responsibilities. Look for roles your boss is in. Look for roles that are similar to yours with a Sr. title next to them. Look for articles that contain advice on advancing in your career (this can shorten some of your research pain). Google the hell out of this and make sure you build a list again of skillsets and experience for these roles (both at full-time companies and for contract positions).

These are your Phase 2 skills.

Now you’re in the spot that you need to be in to understand the future this strategy is sending you on.

  • You need to acquire skills and experience that you don’t currently have that are required for both your bosses skill and for your skillet
  • You need to acquire skills that are required at your bosses level but not yours

We made this easy. We built lists of what the market values for both your position and your bosses position and we simply cross-referenced them and now we have a plan for what’s coming next.

Now that we know this approach, we need to cover how to get level up in this process.

Acquiring More Skills and Experience

There are only six things that the market gives a damn about when it comes to moving up in your skills and experience and they are:

  1. Consulting gigs
  2. Teaching as a side hustle
  3. Certificates
  4. Advanced Degrees
  5. Volunteer activities
  6. Doing your job

That’s it. If you don’t engage in any of these activities and start applying for roles well above you pay grade, I’m sorry but the relatively short rinse and repeat nature of this approach simply will not work for you if you don’t do these things. No discussion. It will just take you longer to climb up the salary scale than everyone else. They’re independent items but these are what the market cares about.

Now, go talk to other people within your industry – just message them on LinkedIn, ask for introductions from friends, family, your boss, whoever – but go talk to them.

Ask them about themselves and how they progressed in their career. Ask them what really think the market is valuing at the moment and what they think you need from this list to make a step up in your career. Ask them where they think your blind-spots are.

Then, go start executing on getting as many of those first 5 items as you can while you keep doing your job.

Where do I find consulting gigs?

This is a huge topic.

The quick and dirty places to seek out consulting and part-time gigs:

  • Craigslist
  • Upwork
  • Industry Events
  • LinkedIn Career Groups
  • Reach out to your network

Disclaimer: It’s not a great idea to tell your boss you’ve been consulting or had a side gig that wasn’t approved by them in advanced. There are often times exclusivity clauses in work contracts or conflict of interest clauses that can essentially get you fired the moment you mention anything about this.

Where do I find teaching opportunities?

We’ve covered teaching in depth as a side-hustle before but we’ll do a quick recap for you to help you understand what we’re recommending

  • Online tutoring
  • One on One Mentorship
  • In-Person course instruction
  • Corporate teaching engagements

How can you level-up your education for free?

First off, ask your employer or perspective employers about tuition reimbursement programs and annual training budget per employee. This is critical.

By free education, I mean accounting cost free, not opportunity cost free. Your time will be sucked up into this for quite some time, but it all matters.

Over the course of my career, my employers collectively have paid for $25,000 of education for me. They’ve paid for advances in hard skills, a masters degree, and strategy training at a one of the top 5 ranked business schools in the world.

Usually your boss needs to approve your tuition expenses in advance so don’t pick something wildly outside your skillset to optimize here. Pick something in consultation with your boss so they feel bought into your successful career growth.

Don’t worry about switching jobs in the middle of getting more education either. It can sometimes hurt to see someone working through a certificate or degree program while they’re looking for a new role. Just list the qualifications that you have learned so far in terms of skills from this experience to date.

Why do this? I recently saw an engineer expense a $500 online course, which they diligently studied over 3 months then take a certification exam for $250 and they moved up their base salary by %7 at their current employer on completion of the course, then they landed a job outside their company for an additional $50,000 pay increase within 2 months of completing the certification. I’ve made salary increase moves before, but nothing compares with that.

How do you get your next raise in your current company?

By this time, you’ve gone and done some of the five activities to level up your skillset above. It’s time to get a raise.

Wait isn’t this approach about quitting up? Yes, it is, and this comes down to item 6 of the above, keep doing your job.

The most important thing to do to get a raise is usually ask for one. It seems stupid but frame it in a way that doesn’t seem blindly ambitious. I usually ask, “What’s the next step for me here? I’ve done XYZ (from the list above) and I’d like to move forward here and if a title change isn’t possible and think I deserve a pay increase.”

Don’t do this every week though. This only works about every 6 to 12 months unless you come in and simply “clean up” and shine as an employee (which should be your goal) at the same time as acquiring more skills and experience. You want to get raises inside your company because your current salary sets you up for the next. Also, salary jumps within a company you’ve already joined are usually much lower than the salary increase you would see by going somewhere else. This is a huge compounding factor in the Quitting Up strategy.

Find Your Next Job

Along with pushing up your existing salary, you need to be looking for jobs. I don’t mean some of the time in your free time, I mean a lot of the time.

You can find jobs through a lot of avenues including:

  • On LinkedIn, Indeed.com, Monster.com, etc.
  • Within your network
  • Alumni networks
  • LinkedIn Industry Groups
  • Industry Reddit forums

If you’re not looking at the market every 3 months, you need to be. I update my resume every month and have done so since I was 24 (that’s a long time ago) to stay fresh and reconsider my options out in the market.

Why do this so aggressively? Changing jobs wins the biggest salary increases when done right.

This along with getting incremental raises at your existing job (above) balloon your salary.

See the examples below:

Nailing down a 20% increase through each job change you have, but also managing a 5% pay jump half way through your tenure at the company – say once a year, the increase over 4 jobs can be 2x your starting salary. On a more bullish note, if you manage a 30%+ pay bump when shifting jobs multiple times in a row, along with getting 5% performance bumps while at your employer – you’re getting 2.54x your starting salary.

If you don’t believe this math, check out the sample below using a fictional starting salary of $50,000. We show the impact of both the 20% and 30% examples along with the intermediary raises between job changes:

Negotiate Your Next Salary

It’s not just about landing a new job. Anyone can make a lateral or downward shift in their career relatively quickly. You need to land the biggest pay increases as a result of changing jobs.

There are entire books on negotiation, so I won’t pretend I can cover this topic here in enough detail but you must ask for as high pay possible when shifting roles and make sure that you have objective facts to push back on a company when you’re doing so.

Be honest with the recruiters and individuals you’re talking to about the compensation you’re looking for in the future. Be prepared with data on what similar compensation is from Glassdoor or other salary sharing or industry or union journals or periodicals that may have this information for you so that you can say the number you want with backing of external

When you do your research and someone low balls you, you need to be able to walk away from the deal without emotion. Understand that you probably shouldn’t quit without at least a 12% bump in total compensation increase. Below are compensation policies that add up to your total benefits:

  • Base Salary
    • Bonus % and Policy
    • Tuition reimbursement policies
    • 401k match and the amount
    • health care coverage
    • Employee Stock Purchase Plans (ESPP)
    • Equity (this can range from future value of nothing to millions)

I’m confident that if you’ve manage to increase your skillset and experience as we talked about earlier as well as negotiate your salary, you can find roles willing to pay you 12%+. There are plenty of times I’ve seen in some instances 50% salary bump increases due to this strategy. The biggest pay increase I landed myself was a 42% salary increase, so don’t shy away for pushing for more if you have the facts in front of you to land a great deal.

What are the barriers to this strategy?

From my own experience and what I’ve seen of others, there are several things that can halt the upward ascent of someone quitting up:

  • Your income plateaus in the field you’re a specialist in
  • There are simply no more title increases you can achieve with your level of experience in your current field or specialization
  • Your industry or employer simply doesn’t make this even a basic possibility
  • Geography

Software engineers often hit the first of these – with high incomes, they can hit a ceiling with their salary as an individual contributor that limits their upward ascent. Hint: think about management.

In terms of level of experience, sometimes you hit hard walls when you want to advance further. I’m hitting one now and it sucks. I’m hearing a lot of “no” back from recruiters, but, there are options that I’m actively pursuing that could land me a 50% pay increase if I land the right company by shifting my focus. These positions aren’t a far jump from what I’m doing now so I’m getting the skills I need through a certificate course and hustling by blogging (not here) to make the change happen for me.

Remember way back when we talked about homework? We had a tactic for executing on our understanding of the market and what it values right now as well as what it values for our bosses position. All this data is useful for finding out if your field even allows for you to execute this strategy.

In the military, government, or a union? Most of the salary range data is available for almost all positions either directly or with a quick online search. You are likely to find some hard barriers to growing your salary in these fields using the quitting up method because most likely you simply can’t quit and rejoin the same industry without having to start all over again.

Stuck in one location without a single good job for your next step? Maybe move.

All of these call for some kind of pivot. Maybe this is where you smell the roses and ask yourself if the industry you’re currently in is even worth pursuing if you can’t multiply your income by quitting up.


If you’ve made it this far, great. A lot of other people have either called this strategy crazy or think it’s unattainable for their situation right now. Fair.

But from my experience and from the experience of a few others I know that this strategy can work and has worked out great for me.

Before I leave you, I do want to say one thing about being content. Being humble and content throughout this process is key. You don’t want to come off like an overly ambitious jerk. You want to set yourself up to quit as much as possible into the best financial situation you can find for yourself.

Who is rich? He that is content. Who is that? Nobody.” – Benjamin Franklin