Anyone looking at the numbers on a sheet of paper would probably think I’m insane.
I was earning well into six figures in sales, investing thousands of dollars most months, and had just bought my first duplex.
And I actually liked my job.
The environment was fun. I got along with my coworkers. There was a lot of camaraderie. More importantly, I knew how to win. I had my routine down, I was confident, and I had become one of the better-performing reps in my division.
Those are pretty good golden handcuffs.
Then I left.
I took a business-to-business (B2B) sales job where I’m making substantially less money right now, learning an entirely different side of sales, and looking at an expected ramp of around 18 months.
It was a really difficult decision.
I still don’t know if it was the right one.
Everyone talks about taking a step back to move forward. What scared me was the possibility that I was just taking a step back.
The money was a huge part of that. So was the feeling that I was walking away from something that made me feel successful.
I had to reconsider what I actually wanted
For a while, my plan seemed pretty straightforward.
Make as much money as I could. Keep my expenses reasonable. Invest aggressively. Buy real estate. Keep doing that until work became optional.
And honestly, staying at my old job might have been a very good way to do it.
But at one point in my personal life, I had to seriously consider the possibility that I might need to move to another city or state. That forced me to confront something about my career that hadn’t bothered me nearly as much before: it wasn’t very portable.
My job was heavily oriented around being in the office. If my life changed geographically, I wasn’t sure my career could easily change with it.
I mostly pushed that thought down and kept succeeding.
Over time, though, I started thinking more about what I actually wanted my career to make possible.
I want to be able to visit family more. I want to travel and explore more. I want more control over where I can work and, eventually, where I can live.
Traveling internationally has become a pretty important part of my life. Sometimes that means exploring somewhere I’ve never been. Other times it means going to a wedding or visiting family overseas I haven’t seen in a couple of years.
I love seeing how other people live. I’m a huge history and geopolitics nerd, so being somewhere with a different culture, history and way of thinking genuinely excites me. It also reminds me that the way we live in the U.S. is only one version of normal. Sometimes people slow down more. Sometimes they prioritize different things. I don’t come home from every trip with some profound revelation, but I usually come back seeing my own life a little differently.
I don’t want those experiences to be something I’m constantly trying to squeeze around my career.
Basically, I want to enjoy my life.
That doesn’t mean I suddenly stopped caring about money. If anything, I’m probably more financially ambitious than ever. I want a career with enough long-term upside that I can make a lot of money and use that money to create more freedom in my life.
I started wondering whether the career I was succeeding in was actually moving me toward that combination.
I wasn’t sure that particular path had the long-term ceiling I wanted.
And there was another career goal I’d mostly put on the shelf.
Earlier in my 20s, I had worked in B2B sales development. I was setting meetings for account executives, but I wasn’t the person actually owning the sales cycle.
I wanted to become that person.
Then I got really good at something else.
Ironically, the more successful I became, the harder it was to justify leaving to pursue something I had wanted before I was making enough money to be afraid of losing it.
Then a recruiter messaged me
I wasn’t desperately applying to jobs when a recruiter reached out to me.
What caught my attention was the title: Account Executive.
The company was also in security technology, so it wasn’t completely foreign to me. I had been selling residential security monitoring. This opportunity would keep me around an industry I understood while moving me into a broader B2B role.
I’d be dealing with businesses, different technologies, more complicated problems and multiple stakeholders. Instead of setting meetings for an account executive like I had earlier in my career, I’d actually own the sales cycle.
The role also offered substantially more flexibility in where and how I worked.
I love traveling. It’s not that I’m dead set on living in some particular country or bouncing between cities constantly. I like knowing that I can.
I like being able to handle a doctor’s appointment or something else that comes up during normal life without feeling like my physical presence in an office is the point of the job.
Funny enough, I also think I’m often more productive at home. My old office was so much fun that sometimes the distraction was the people around me.
Remote work definitely isn’t automatically better. For some people, it can probably be terrible.
I just know what works for me.
The argument for staying in the higher-paying job was really fucking good
There was nothing obviously wrong with staying.
I wasn’t fleeing a horrible boss. I wasn’t broke. I wasn’t failing. I wasn’t waking up every morning miserable about going to work.
I was leaving something that was working.
I could have stayed, continued making very good money, invested aggressively and potentially reached financial independence faster.
That argument still bothers me.
If I could invest thousands of dollars every month on the old path, every year I spend making substantially less somewhere else has a real opportunity cost. That lost money doesn’t just disappear from this year’s income. It’s also money that isn’t invested and compounding.
So the new path couldn’t just be “more interesting.”
It had to give me a better shot at building the life and career I actually wanted.
What I thought I was getting in return
In practical terms, I’m taking a massive short-term pay cut.
But I don’t think of this as choosing a permanently lower-paying career.
I’m betting that the drop is temporary.
I saw a realistic path toward eventually matching or exceeding what I had been earning. I also wanted something valuable even if this particular job never became as lucrative as I hope it will.
I wanted B2B experience I could actually point to.
I wanted to learn how to own a more complex sales cycle, work with multiple stakeholders, understand different business functions, solve larger problems and produce quantifiable results.
If I eventually leave this particular role, I want to leave it having opened doors that weren’t open to me before.
And I wanted a career that could fit more easily around the rest of my life instead of requiring the rest of my life to fit around my career.
That combination mattered more to me than simply maximizing what I could earn this year.
I also made sure I could afford to be wrong.
I’d spent the previous years investing aggressively. Rental income was offsetting some of my housing costs, and I hadn’t allowed my lifestyle to expand enough that I absolutely needed my previous income just to maintain it.
My previous success, in a weird way, helped buy me the ability to take the risk of leaving it.
I tried to research the uncertainty out of it
Before accepting the job, I did probably more research than a normal person should.
I went through LinkedIn looking at people who worked at the company. How long did they stay? What did their title progression look like? Where did they go afterward?
I deliberately searched for the negative stuff too. I researched the position, the company and my market. I asked my potential manager a lot of questions.
Because my biggest fear wasn’t just making less money for a while.
It was spending 12 or 18 months ramping, only to discover that the opportunity I’d been ramping toward wasn’t actually there.
Maybe the territory wouldn’t be good. Maybe the support wouldn’t be there. Maybe the products or service wouldn’t be competitive enough. Maybe the income potential wouldn’t be as realistic as I thought.
Or maybe I’d simply suck at it.
Research could reduce some of those unknowns.
It couldn’t eliminate them.
Eventually, I had to make a decision with incomplete information.
Fuck it, I’m doing it
Before leaving, I tried to see if I could make my old role fit what I wanted.
I had a conversation with leadership about the things that mattered to me, particularly flexibility. Ultimately, the company couldn’t offer me the arrangement I wanted.
A couple days later, I thought about the other opportunity again.
The upside. The lifestyle. The chance to solve more complex business problems.
And my younger self.
Before I had the income I was now scared to give up, I’d wanted to become a B2B account executive.
Now I actually had the opportunity.
At some point, there wasn’t another spreadsheet to run.
Fuck it. I’m doing it.
I told my manager I was leaving.
I was excited, but I also remember having a pit in my stomach. Being back in the office and seeing everyone made it feel real. Oh my God. I’m actually doing this.
And almost immediately, there was still a part of me wondering whether I’d just walked away from something really fucking good.
Going from mastery back to apprenticeship
I’m only a few weeks into the new role as I write this, which is exactly why I don’t want to pretend I know how this story ends.
What I can already tell is that my brain is being worked differently.
I’m focused on financial institutions now. Instead of talking primarily with residential customers, I have to understand different business functions and stakeholders: operations, facilities, security, risk, compliance and finance. I have to figure out what each of them actually cares about.
Then I have to understand whether something we offer can solve a real business problem and connect all those pieces.
The rhythm of sales is different too.
At my old job, volume mattered. I was making a lot more calls, talking to a much larger number of potential customers and closing far more individual sales.
Here, the pool of potential buyers in my territory is much smaller. The sales cycles are longer, there are more people involved in the decision, and the individual deals can be significantly larger.
I have to be much more strategic about each account. I can’t rely on pure volume the same way.
That’s uncomfortable.
I went from knowing exactly how to win to being a beginner again.
I was used to getting immediate wins and having constant proof that I was good at what I did. Now I can put in the work and still not know for a while whether I’m actually good at this.
But I’m also realizing I’m not starting from zero.
The titles are different. The stakes are different. The buying process is more complex.
They’re still people.
I already know how to build rapport, make people comfortable, ask good questions, listen for what’s actually important and get beyond surface-level answers. I’m now doing face-to-face versions of things I spent years learning to do over the phone.
The foundation transferred.
I’m just building something different on top of it.
How I’ll know whether this was worth it
A year from now, I want to see meaningful progress in my territory.
I want evidence that difficult accounts are still penetrable. I want a few customers and relationships that are genuinely becoming mine. I want to see good support from my company, good products and service, and customers who are actually happy with what we’re providing.
I want to be substantially better at B2B sales than I am today.
And yes, I want to see the income gap starting to close.
Progress in a longer sales cycle isn’t always going to mean closing a huge deal. Sometimes it’s a meeting. Sometimes it’s finding the right stakeholder. Sometimes it’s learning one new piece of information about an account.
One small win at a time.
But eventually those wins need to turn into something measurable.
If a year from now I’m still running in circles and I can’t see a believable path toward the skills, customers or income I was trying to build, I’ll have to seriously question whether I made the right decision.
Maybe I’ll conclude that I should have stayed where I was.
I don’t have the lesson yet
I don’t think the lesson here is that you should leave a high-paying job.
I also don’t think it’s that you should take a pay cut for career growth, “bet on yourself,” or choose freedom over money.
Those are nice things to say after everything works out.
I don’t know if this will.
If you’re thinking about leaving a good job for a different career path, get very specific about what you actually want your career to make possible in your life.
Money matters. So does flexibility. So do the skills you’re building, the opportunities you’re creating and what you actually want to do with your time.
Those things are going to look different for everybody.
For me, I want to make a lot of money. But I also want to visit my family, travel, explore, have more control over where I spend my time and actually enjoy the life I’m working so hard to build.
I’m trying to find a career that gives me a better shot at both.
Maybe this one will.
Maybe staying, making as much money as possible and continuing to invest aggressively would have gotten me there faster.
I genuinely don’t know yet.
That’s why I’m writing this now instead of five years from now when I can pretend the answer was obvious.