When You Feel Guilty About the Life You’ve Built for Yourself

Sooooooooooo okay, I kinda mentioned last week that I should do a post about money and careers and guilt and shame, and you kinda said you’d want to see a post about that, soooooooooooo here we go.

I didn’t start asking myself whether I should feel guilty about the life I’d built for myself until I bought my piano. Prior to that, my work life didn’t include anything uniquely outstanding; I worked from home, but so do a lot of people. I earned $68K in business income minus loss, but so do a lot of people. Sometimes I took 30 minutes at lunch to walk the trail next to the river, but I’ve been doing that kind of thing ever since I got my first office job, and while there’s privilege in being able to go for a walk during your lunch break, it’s a privilege that’s available to a lot of people.

And then I got a piano, and I began using that piano as a way to refresh my mind between freelance pieces, or to hammer out an idea while I banged at the keys.

And that is a privilege most people can’t access during the workday.

So should I feel guilty about it?

And if I do, what should I do about it?

Let’s take a moment to clarify the difference between guilt and shame. Brené Brown, who seems to be the expert on these kinds of things, defines guilt as “I did something bad” and shame as “I am bad.” When I started to search for words to describe what I was thinking and feeling so I could write this post for you, I was thinking of guilt as “I lived according to my values, yet I feel bad” and shame as “I went against my values and I feel bad.”

Because there needs to be a word for “I lived according to my values, yet I feel bad,” as well as “I lived according to my values, and people were hurt, so I feel bad even though I know I did the right thing.”

(Is there a word for that?)

For example: shutting down The Billfold was a for-sure instance of “I lived according to my values, and people were hurt (or at least disappointed), so I feel bad even though I know I did the right thing (for me).”

Is the word to describe that feeling guilt?

What about the feeling you get when you set a boundary with someone and you know they are hurt/disappointed/angry/frustrated with you and yet you know the boundary had to be set and yet you feel terrible?

Or, to bring it back around to where I started: how do you describe the feeling, much less deal with it, of having shaped the life you wanted for yourself while knowing that not everybody can shape the life they want?

And then you have to interrogate whether that’s really true, because there are certain philosophical theories that suggest we always do what we want, even when “what we want” means “choosing the better of two bad options.” (As you might remember from my review of The Courage to Be Disliked, this extends to behaviors that we outwardly claim we did not want to do, whether that’s yelling at a waiter or ignoring that boundary we told ourselves we’d set. The desire to yell was stronger than the desire not to yell, etc. etc. etc.)

But if you head down that path you end up with “people put themselves into their own bad situations,” and that is demonstrably not true (hello, systemic inequality) so I’m just going to step aside from that whole discussion and go back to the question I’m currently trying to address:

Should I feel “guilty,” where “guilt” is a stand-in for a word that means “I lived according to my values and yet I feel bad,” because I have built a life that I really like, and, like, not everybody gets to do that?

We could also ask, because it’s fair to ask this question at this point in the piece, whether this is an indication that my values themselves are suspect. If I lived according to my values and I feel bad, does that mean my values should change?

Well… I mean, I feel like I’ve been refining and maturing my values as I continue to grow, and I’ve begun to adjust some of my values accordingly (“independence from parents” shifting towards “integration with parents,” for example).

So, with the understanding that I may want to change my current set of values in the future, I am currently fine with them.

Because, once again, this feeling of “guilt” is different from the way I feel when I do something that goes against my values.

For example: early in my freelance career I took a gig from a client whose work went against my values. I did not know the work went against my values when I accepted the gig (it was one of those early-career content mill things where you wrote unbylined copy to spec for pennies a word and allowed the client to use the copy however they wanted) and it took me a while to figure out where my assignments were ending up.

I don’t feel shame for accepting the gig or writing the first handful of assignments for this client. I feel deep, deep shame for continuing to work with the client for five months after I realized that they were paying me to write scammy SEO posts to help promote junky products and services.

To my credit, I spent much of that time asking friends whether I should quit (and they said no, but we were all in the “crappy jobs” period of our lives so this didn’t seem too different from the rest of the workplace); I also spent a fair amount of time trying to decide whether I was just being an idealistic Millennial (because that was when they were writing articles about idealistic Millennials trying to tell established companies how offices should be run). This was literally my second freelance gig ever; was I right to feel weird about it, or did I not understand how the industry worked?

To my discredit, one of the reasons I kept working that gig was because I needed/wanted the money. However, I quit the gig the minute it went from “against my values” to “so overwhelmingly against my values it could no longer be ignored,” without anything lined up to replace it. Then I gave myself the assignment of paying back everything I had earned from that client, in a combination of charitable donations and volunteer hours (because I wasn’t earning gobs of money yet and I still needed to pay my rent), and I did it.

And yet I still feel deep, overwhelming shame every time I think about the time I spent writing for that client. Even though I learned from it, did everything I could to pay back what I’d earned from it, regularly teach other freelancers how to avoid those kinds of gigs, and have never taken an assignment that has gone against my values since.

So that’s the difference between guilt—or this feeling that isn’t exactly “guilt” but I don’t have a word for yet—and shame, at least to me.

Guilt asks me to interrogate my decisions, my boundaries, my obligations to others, and the choices I want to make going forward.

Shame asks me to once again convince myself that I’m not really a terrible person, even though I probably am, because I’ll never be able to undo that mistake.

If you feel shame about your current life or career, that’s worth addressing immediately (please don’t spend five months asking yourself if you should ignore your bad feelings about the whole thing, it will only make the shame worse in the end).

But if you feel guilt, or something akin to guilt, because you have put together a life that’s personally and/or creatively satisfying and fits your current set of values… what do you do then?

Let’s continue this discussion tomorrow. ❤️