Saying Goodbye to Six Figures

I have a full-time job. A dangerously good one. My hours are flexible. My pay good. My PTO ample. My benefits through the roof. My oversight slim. Not once in three years have I been reprimanded by my boss.

I have it made.

But I have the urge to leave despite all of that. I want to make new things. I want to write more and play more. I want to focus on myself. I want to feel alive in a way that I don't currently feel. And I crave change.

But I also don't want to leave. The job is awesome, after all.


This is my second full-time job. My salary now is exactly double my salary from my first full-time job. I don't know which of those salaries is closer to being fair. I don't know which of those my work is worth.

Including the income from my side business I earn just over $130,000/yr.

Out of respect to my employer and my coworkers, I'm not going to give a break down of how much comes from my full-time job and how much comes from my side business.

I respect that most people don't like discussing finances. I don't either. Until today only two people in the world knew my income. I'm disclosing it here only because of its pertinence to this decision. I don't know how to write this post without mentioning it.

If I quit it won't be to get a new full-time job. It will be to pursue my own ventures. That pursuit might fail. Some might even project that failure is probable.

I might have to, or want to, go back to a 9-5 job in the future. In doing so, I don't know which salary I'll go back to. I might take a 50% pay cut. I might have to face the fact that I'm not worth my current salary. Can I live with that?

Financial Education

I had a fortunate upbringing.

My parents made a lot of sacrifices for my brother and me. My mom sacrificed her career to raise us. She sacrificed her nights and her weekends to take us to soccer and basketball. She sacrificed time with her friends for time with our friends. She was the best mom a kid could ask for. In hindsight, at least.

My dad sacrificed those same nights working long hours to provide for us financially. He sacrificed those same weekends watching our games and swim meets, playing catch with us in the backyard and roasting marshmallows with us. He was the best dad a kid could ask for. In hindsight, at least.

Not to mention the financial sacrifices. Delaware's public schooling system is notoriously bad, so vacations and new cars were foregone to send us both to 13 years of Catholic school (I think I'm still recovering from that experience, but that doesn't make me appreciate it any less). Padding the retirement fund was foregone to pay for our college educations.

And those were just the most obvious financial sacrifices. From a developmental standpoint I had everything I could have ever wanted growing up. No, I wasn't spoiled with every single toy I wanted. But I always had whatever I needed and then some.

One of the reasons I was so well provided for was because my parents were both great with money. My mom graduated with a business degree. My dad is an accountant and Certified Financial Planner.

I was lucky to have a home-grown financial education included in my childhood. I understand the value of compounding interest. I know the tax benefits and trade-offs of 401ks, traditional IRAs and ROTH IRAs. I know the yearly maximum contributions for each of those and the how that maximum differs based on circumstance. I understand stocks and bonds, loans and mortgages. I know how to do my taxes the old fashioned way. I understand debt and I understand savings.

Or in other words: I truly understand the difference between making $130,000/yr and, say, $50,000/yr, and the implications that that difference can have on my life. I understand the freedoms, the luxuries and the security that comes along with the former. I understand what the difference means for our future and for the future of any hypothetical children we may one day have.

It is because of this financial understanding that quitting my job to pursue my own path is not an easy decision.

$130,000 will fall well below six figures in that first year of self-employment. It may climb back up. But it may not.

Again, I'm not going to disclose how far I expect it to fall because - out of respect to my current employer - I don't want anybody to know how much comes from my salary and how much from my side business.

And here's a harsh reality I just had to swallow: $130,000 is important to me far beyond its utility.

It took some soul searching and a few glasses of wine for me to admit and confront this fact. The fact that I make more money than most people makes me feel good about myself. That's something that I hold as a core value. That's painful to admit. I recognize how messed up that is. But that doesn't make it any less true.

By threatening to take away that value I'm threatening my self-worth. What if I make less money? Can I live with that? Would people think less of me? Would I think less of myself?


My dad is an entrepreneur. When I was a young child he left his safe, secure job at Wilmington Trust to set out on his own as an independent accountant and CFP. I remember that my parents were very careful with money those first few years during my dad's transition. Whether we "struggled" or not I couldn't tell you. There was always food on the table and I was too young to notice anything beyond that. My mom did a great job of shielding me from worries that I didn't need to worry about.

Because of the sacrifices my parents made, and the risks they took, I have a weird sense of accomplishment from my current salary that I don't think I'd otherwise have. I have a sense of "Look! You sacrificed for your family to put us all in a better position. And you did. And I got such a head start because of it. And I made the most of it. Look at me now!" And even though I've never told my parents my salary I have this screwed up vision of them smiling and being proud of me for it.

Which couldn't be any more idiotic. My parents - both of them - are proud of me for being me. I know this for a fact. When you spend enough time with people you can know for a fact certain things that make them happy and proud. And I know for a fact that they are proud of me when I'm true to myself, even if they hate it.


Sarah (my wife) loves me. She wants me to follow my path. She's comfortable supporting me while I get started down that path. She's comfortable with the idea that I may never get back to six figures. She doesn't care. All else equal, of course, I'm sure she'd prefer more money than less money. But she doesn't base her love on that. Not even a little bit.

This means that I'm worried about hurting her in a way that she can't be hurt. I'm scared that I won't be able to provide for her. But she doesn't need me to provide for her. She doesn't even want me to.

If Sarah doesn't need me to provide for her then why do I so desperately want to? Maybe it's because my dad was able to so admirably provide for his family. Maybe it's because a lifetime of movies have told me that, as a man, I'm only valuable if I can provide for "my woman".

Maybe it's because I'll be forced to rethink my identity if my wife makes more money than I do. But the simple fact that I typed that sentence means I need to rethink my identity. I have some whacked-out values. But I'm aware of them. And I'm fixing them.

Why Not Quit?

Quitting might mean fewer vacations. But probably not. Probably just a little heavier on the camping side and a little lighter on the fancy hotel side. I can live with that.

It might mean a 6-year-old car instead of a 1-year-old car, $60 shoes instead of $90 shoes and a $35 hoodie instead of a $135 hoodie. I can live with that. But again, it probably won't come to that. I buy very few things.

It might mean going out to eat a little less often. Not only can I live with that, but I'd love to live with that. It's time to make that change in my life regardless.

It would mean less money in the savings account and less money in the retirement account. That sucks. But I can live with it.

It would mean reevaluating my worth as a programmer. Am I worth $130,000? I don't know. What if I need to get another full-time job and my best offer is $40,000? Never mind the financial implications, what will that do to my ego? Screw my ego. I can live with that.

It would mean less structure. When I take a step back this is what concerns me the most. One morning I might wake up uninspired and set off on a 6-week Netflix and Facebook binge. Or at any point of struggle I might turn on the TV, open a beer and pack it in for the day, never mind that it's 10AM. But there are ways to help with this. I think I can make this part work. And if not, I can live with my failure.

It would mean accepting that my ideas might suck. Or that my execution might suck. Or both. Right now I have great ideas. But I don't pursue them. So of course they're great. There's no feedback telling me the opposite. As soon as I execute my ideas, though, they get the litmus test. What if they aren't great? What if people hate them? Worse, what if people don't even notice them? For the first time in my life I'm at a point where I can live with that.

It would mean accepting that I might not be able to work for myself. I might not have the discipline. I might not have the fortitude to push through when things get tough. I think of myself currently as someone who could easily make it on his own but is choosing not to. Quitting my job means testing that thought, and potentially being wrong. I can live with that.

It would mean confronting previous failure. I've already tried and failed once as an entrepreneur. But I also sucked the first time I played disc golf and yet I went back to play again. I'm different in almost every way than I was back then. I'm probably different in that way, too.

Perhaps most eerily, it forces me to answer this question: Do I truly have better things to do with my life and will I do them? I whisper all the wonderful, meaningful things I could do with my life if I didn't have a 9-5. But could I actually do these things? Would I actually do these things? Or are they just "grass is greener" dreams that will be forgotten or dismissed?

What would it mean if I quit my job to pursue my dreams but then didn't pursue my dreams? What if all I'm capable of doing is dreaming? To be honest, I don't know if I could live with this. This scares the feces out of me. But I have to find out.


I have held this same job for over three years. Not in my life have I ever done something so routinely for even one year. This is not like me.

My mind is becoming numb from sameness. My body weak from sedentarism. My spirit challenged by lack of challenge.

The absence of pain in my life is painful. I need pain to grow. Lack of growth in life is painful in a way that being unable to afford a vacation never could be (from the perspective of someone who is fortunate enough to never have had true financial struggles).

I'm too comfortable. And so I've never been more uncomfortable. Too much of a good thing is not a good thing. Too much safety is dangerous.

You may say "here's this guy with the world's easiest life. What's he complaining about? Is his brain broken?" And to you I say a) I am not complaining. I am thinking out loud. Asshole. and b) I do not want an easy life. My brain may be faulty, but it is the one I have to work with. And work with it I will. I will not attempt to mold it into something it is not. Such molding would not work.

Will I subject myself to chaos and uncertainty, building myself stronger each time I am broken? Or will I wither away in the conveniences and safeties of life?

What stress will I embrace? Will I get upset because my favorite TV show was canceled? Or will I choose to care about actual problems?

My Decision

In the "why not quit" section I never once mentioned something I'd miss about my job. Perhaps that's telling.

There would be plenty that I would miss. A ton. The company I work for is awesome. The job is great, the perks are great. My coworkers are, for the most part, great. All of that. But I've long ago made up my mind, even if only subconsciously, that I need something else. So the aspects of the job that I like are almost secondary.

My reasons for not quitting are all related to my insecurities. That's something I can't live with. And so, by the time this post finds the Internet I will have handed in my letter of resignation. Now it's time to get to work. Work that I care about.

Am I scared? Indeed. But I've also never been happier. I've never felt more alive. For the first time in years I find myself jumping out of bed in the morning.

I'm So Lucky

For a long time I tricked myself into thinking that by having a high-paying job I had more to lose.

Nothing could be further from true. By having a high-paying job I was able to tuck away a little savings. I'm laughably far from rich. But if it takes me eight months to get my side business profitable? I can withstand that.

What I'm doing is risky, no doubt. But it's a feasible risk. It's a risk that I'm able to somewhat-comfortably take, and I'm so thankful for that.

What Will People Think?

Most people (that care at all) aren't going to like this decision. I know this for a fact, because I've already told a few people. The condescending voices have and will continue to be plenty. People will continue to think that I'm an idiot that doesn't know a good thing. People will continue to think that I'm a lost hippie.

Those people might be jealous that I had the courage to do this. Or they might genuinely think that I'm an idiot. Probably a touch of both if I had to guess.

I wish I could convey to you just how little I care.

I'm not trying to put on a facade. I do care what people think about me. But only certain people. And those certain people, at worst, would be neutral about such a decision.

What About You?

I'm not encouraging you to quit your job. I'm not encouraging you not to, either. I'm just talking.

I don't hate 9-5 jobs. I don't hate "the man." I don't think everybody should quit their jobs and work for themselves. I just needed, for myself, to try something different for a while.