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Office Space - Peter and the Bobs

Sabotaging My Way to Success: Work, Money, and Purpose

So I had a call earlier this week with a listener of my old ​Maker/Mistaker podcast​.

She wanted to ask me about ​my experience at the Monroe Institute​ (a center for consciousness research and out of body exploration). She also wanted to ask about hiring me to help her with a logo and a website for her new coaching practice.

We had a great call, but I left feeling kinda discombobulated. Out of sorts. Confused and a little bit vulnerable.

This call got me all mixed up inside because it exposed how conflicted I am about what I’m meant to be doing with my life. Confused about money and work and my purpose.

I felt like I forgot how to do business. Like I self-sabotage my own ability to sell my self as a designer because I’m too honest and forthcoming. It seems like a cosmic joke that when I’m hard up for work, I get a potential client asking me to do something for them, and I all but talk them out of hiring me!

So what happened?

We talked for over two hours. It was an incredibly real, open-hearted and genuine conversation. It felt like we had known each other already and we jumped right in to talking about life’s biggest questions.

Perhaps this is because they felt like they knew me from listening to a bunch of my podcast episodes and right out of the gate, we’re talking about divorce, betrayal, spirituality, Christ consciousness, ascension, mysticism, truth, love, freedom, etc.).

All of this was very enjoyable for me. I love talking and listening. Being present. I can feel my higher self there with me.

But then when it came time to talk about hiring me for design, I got a little insecure and nervous. She asked if I was interested in building her a website and doing an illustration for her new coaching business.

In my radically honest way, I said I certainly can help her with that stuff, but my web design skills are not up to date, but I know someone who is that I could refer her to. Sure, I’d be happy to do what I know how (set up a WordPress site and customize a theme). I’m not a real web developer. Really, I just wanted to help her get what she needs, even if that means not hiring me.

Strike one? I could have just said yes, but no, I disqualify myself in the name of being honest. I couldn’t even have lied because my body language will betray me, especially to someone who seems very perceptive and aware.

And it did. My body language was visibly more inward and not showing an elevated passionate response to the idea of designing this stuff for her. Even though I call myself a designer, I’ve been largely out of the “game” for quite some time.

Sure I have done maybe a dozen freelance gigs over the last few years, but design is not the skill I have spent the past decade practicing. I have honed my skills in emotional attunement, feeling feelings, healing trauma, mindfulness, developing presence, critical thinking, spiritual integrity, etc. But those aren’t going to pay my mother freaking billzzzz. 😬

Design is how I make money. Design is one thing I do for work that when I do it, it pays the most. A lot more than my Etsy shop or any of my passive income streams. So it’s what I say when people ask me what I do for work. Even though I’m also a writer, podcaster, and music producer, and whatever other thing you’d call a creator these days.

I love “making cool shit and making shit cool.” I also love getting paid for it, but am growing increasingly more weird about money, so…. I told her up front that I didn’t even know what to charge these days, just that I wanted it to be fair.

Strike two? I don’t even know what I’m doing lol

She noticed I seemed a bit off and jumped in to reassure me. To try and save me from embarrassing myself. She said I didn’t need to be on the bleeding edge of web design, she just needed something simple. Like a one-pager. Cool I can do that.

She also described an idea for the illustration she had in mind. Something mystical and angelic, something you might see on a spiritual life coach website. She commented how much of the designs in my portfolio are ​dark and a bit morbid​. Yes, that’s what you get after years of doing merch for punk and metal bands. Besides, I appreciate the dark elements. My style is not exactly love and light.

Again, as if I was compelled by a force greater than me, I just couldn’t lie or sell myself in any way other than being real and genuine. It’s like if you’re in an interview and you admit that you’re just there because you need to make money.

I mean, that’s usually how it is at every job interview. But you’re not supposed to actually say that out loud. You’re supposed to pretend like you would love to work for their company and dedicate your life to their business. And say the right things and sell yourself accordingly. Certainly not tell them how you really feel!

It’s like that ​scene in Office Space​, one of my favorite movies. When Peter Gibbons has his meeting with “The Bobs” and just speaks freely, totally not giving a shit about working there. And the Bobs are totally thrown off guard but secretly impressed with his audacity. They offer him a promotion and a raise.

Peter and the Bobs from Office Space (1999)

That was me at times in this call when it came to work. At least one part of me was like that. The other part was like ​Michael​, Peter’s co-worker. Kicking himself for acting so foolish. How am I going to get hired if I am acting like that? I must be an idiot!

As we talked further, she put on her life coach hat and asked me if doing design was what I really wanted to do with my life. She could sense that I felt a bit off when I talked about it and we explored it more. Was I just being insecure given the conversation?

When I dug deeper, it’s not that I don’t like design. It’s that I don’t like how it feels when I’m designing. I sometimes have a really hard time executing the work. I can be such a perfectionist, that it never seems quite good enough. I worry a lot about doing it right and pleasing my client. I often spend way more time than is budgeted, but I don’t charge for that full amount because that’s my problem, not theirs.

I said that sometimes when I do client work, it feels like the stakes are really high. That a lot is riding on me executing and impressing them. My design process sometimes feels like I’m glued to my computer screen trying to solve or fix this problem that isn’t quite working and it’s really frustrating.

Despite having 20 years experience, I feel like I suck. I feel like I’m not as good as I used to be. That I’m out of practice. That I’m not worth what my client is paying me. That I’m only as good as the graphics I’m creating.

All of this was not really helping my case for landing this client. She was already willing to hand over cash for me to work on her project. And boy, could I use some cash right now.

Speaking of which, I could feel this kind of needy, hungry, desperate energy within me. This part would do pretty much anything to get some money so we can pay rent this month. And it’s absolutely floored that other parts of me were sabotaging this opportunity by being “radically honest.”

Meanwhile, she’s getting a kick out of all of this. She’s helping me work through my conflicting feelings about what I really want to do with my life. She wants me to thrive and flourish and do what I’m meant to do on this planet.

She asked me what really lights me up if it’s not design?

I said, well, THIS conversation right here does. I love this. Talking and being real. Listening and being of TRUE service. Where my unique presence is valued and not just my artistic skills.

I loved the conversation because it felt organic and present. With a real live human being. Not me hunched over my computer, cramping my hand with my drawing tablet working through draft after draft of mediocre design work.

Look, I know my design work isn’t “mediocre” – I am self deprecating here. Every artist I know feels like their work isn’t as good as it could be. Certainly not compared to their contemporaries. All us artists are aware of the gap that exists between our taste and our skills. So it’s usually a pretty humbling experience working on any design project because we are always challenging ourselves to get better. So you’re always aware that you’re just not quite good enough.

We talked more about what lights me up.

Where could I have fun conversations like this?

On a podcast duh.

She went on to say how much she loved my Maker/Mistaker podcast, even my ​solo episodes,​ because I was so genuine and the flow of my ideas came out so naturally in a way she really connected with. She wanted me to do more of them.

I really appreciated hearing that. I said I stopped doing my podcast in 2016 because I started to get self conscious about sharing myself so transparently online. It was a really toxic environment at the time because of the Trump election cycle and how enflamed the culture wars were getting.

I was exploring some ideas that were different from what people knew of me and I was worried about being misunderstood, criticized, or cancelled. I wanted to explore and grow and heal without putting it all out there in public to be scrutinized. So I stopped posting much.

A lot of time has passed since then and I’ve been feeling the itch to “put myself out there” again.

(On this subject, check out Brooke Erin Duffy’s presentation on The Promises and Precarity of Platform Labor. “Shedding light on the contradictions inherent in the new realm of creative work, this research provides valuable lessons for anyone roused by the siren song to “put themselves out there.”)

That’s one reason for starting this newsletter and for the new podcast project I’m doing with Zach Hendrix that should be launching soon. We’ve got three episodes in the can and are working on some other logistical stuff before we launch it.

In addition to that podcast, I kinda just want to reach out to other people who have inspired me in some way and talk to them. Maybe post those conversations to my ​YouTube channel​ or start up my solo podcast again.

I still won’t rule out design or art though. I like making cool images. Especially for bands, clothing companies, and indie creators. Stuff that suits my style and allows me to just be me, in visual form. Without a lot of high pressure or stakes. I gotta ease up on my perfectionism and people pleasing tendencies.

But right now, podcasting doesn’t pay the bills. But maybe it can?

I have so many weird conflicting beliefs about money, work, and capitalism. While everyone can agree that the system we live in sucks and is exploitative, you’re just not supposed to talk about it. If you do, you’re a juvenile teenager or a lazy commie who doesn’t believe in hard work.

All of these thoughts and beliefs are jumbled up and confusing right now. Things are in flux. I’m questioning everything.

I don’t think I really sabotaged anything in my call this week. She appreciated it. And I am thankful that she came into my life to help me work through these feelings. To help me untangle the web.

Zach and I will explore these topics more on our podcast. That’s why we’re calling it We Should Be Working. We hope that by doing so we will arrive somewhere that helps us get to where we’re meant to go. We hope it will help others too.

What Else I’ve Been Into:


  • I had a call with Sean Dadashi, co-founder of ​Rosebud​. They were just doing customer outreach to get my feedback after I cancelled my premium subscription. I gave them way too much “Jeff style” honest feedback (hint: probably oversharing lol). But that’s kinda what they’re after. We discussed the paradox of technology and wellness, when apps need you more than you need them, etc. It was a good talk!
  • Worked on a music intro for We Should Be Working. Had a major perfectionism attack and doubted my entire musical creation ability thinking what I make is just cringe. But is it? Going for a punk rock vibe.




  • ​Rukus (2018)​ by Brett Hanover is a “a queer coming-of-age story set in the liminal spaces of furry conventions, southern punk houses, and virtual worlds.” A fascinating discussion of this film by Katherine Dee and Gio ​here​. I enjoyed it.
  • ​1987 vs 2024 NBA All Star Game Comparison​ – For old-heads who think the modern NBA sucks compared to the 80s and 90s. I think I’m one of them.

That’s about all for this week. Have a great weekend!

Talk soon ✌️


Jeff Finley
Jeff Finley

Jeff is a graphic artist, designer, musician, writer, and mystic with a passion for truth and personal growth. He's the author of Wake Up, Maker/Mistaker, and Thread's Not Dead, as well as the creator of Starseed Supply Co. Learn more about him here.

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