Dear Gup and Dabbles,

There are a few ways you can feel stuck. You can feel stuck in a small way, and you can feel stuck in a big way.

Feeling stuck in a small way is generally a matter of not knowing what to do or how to do something.

Feeling stuck in a big way is generally a matter of not knowing why you should do something.

The tricky thing is, sometimes you feel you’re stuck in one way, but you’re actually stuck in the other.

Say you’ve gone to a good college and you’re applying for your first job at an elite, brand name company.

You feel anxious because you don’t know how to network with the right people, answer interview questions in the right way, etc.

You’re stuck because it’s overwhelming and you feel paralyzed by all the things you think you should be doing.

On the surface, you are stuck in a small way. You can research people on LinkedIn or your alumni network who work there or know people who work there. You can research interview questions and rehearse answers.

There are very tactical things you can do to get unstuck in this case.

But sometimes the root of your stuckness runs deeper.

If you asked yourself why you wanted to work at this company in the first place, you may realize that maybe you don’t actually care about this particular company or job at all, but that you just want to be viewed as successful by your peers. Or perhaps you’re worried about falling behind in life and have convinced yourself working at this company is the way to keep up.

Once you realize you’re stuck in a big way, you can become more flexible with solutions.

Maybe in this example you start looking for people who live a “non-elite” life but are still happy. Or you start reading philosophical books about what it means to live a good life and key in on certain values that resonate. There are many options.

But again, it’s tricky to figure out whether you’re stuck in a small way or a big way, so a good solution is to cover your bets simply by asking yourself a small question AND a big question.

You can ask yourself, “What should my next step be? Why should I do this at all?”

If you’ve answered a small question, asking the big question forces you to pause and reflect. It’s a way of checking in with yourself.

If you’ve answered a big question, asking the small question forces you to actually take action and not get stuck in an infinite contemplative loop.

By pairing the small big question and big question, you’ve found a way to move through life, learn more about yourself, and make changes as needed.

Love,

Dad

Dear Gup and Dabbles,

At this moment, I am “unemployed.” The contract I was working on was unceremoniously terminated which means I’m no longer going into the office five days a week.

As someone who has had experience with being unemployed, I wanted to share some ideas that may help you if you ever find yourself unemployed or in a situation where you’re anxious or uncertain about your future.

Don’t force it

As a kid, my dad used to make me help him with small projects around the house, like putting together cheap furniture.

That typically involved screwing or bolting two pieces together or, if we made a mistake, unscrewing or unbolting two pieces.

If the screw or bolt got stuck or we felt an unusual amount of resistance, he’d say “don’t force it.”

Most of the time, the action should be smooth, so if you were getting stuck, that was a clue you were doing something incorrectly and needed to take a step back to assess. If you tried to force it, you would probably strip the threads and mess up the screw, giving you a potentially unstable or lopsided coffee bookshelf.

This is good cheap furniture assembly advice, but it’s also good life advice. If you’re feeling like you’re forcing something, stop and take a step back.

What forcing it looks ands feels likes

It’s not always obvious when you’re forcing it.

In unemployment, “forcing it” looks and feels like frantic motion and emotion. It’s a form of self-soothing in the short term, but does very little to actually move the needle.

Here are some examples:

• Sending out lots of cold job applications, for jobs you don’t actually want

• Tweaking your resume endlessly

• Networking with people you don’t actually care about hoping they’ll just give you a job

• Feeling like you’re not doing enough

• Catastrophizing; thinking you’ll become homeless

• Worrying about being good enough as a person

• Feeling embarrassed about not having a job

As perverse as it is, moving frantically and letting yourself get anxious is a way of feeling like you have more control than you actually have.

But this doesn’t change the fact that this will have very little impact on the results you get. Most things that are forced end up having very little impact relative to your effort and a surprisingly high emotional cost.

You can’t force it, but you can’t do nothing

This idea is uncomfortable because there is a core tension. You can’t force things to happen, but you can’t just do nothing. If you do nothing, nothing about your situation will change.

We’re naturally drawn to stories of grit and perseverance. We love underdogs that make it against the odds by performing heroic efforts to achieve their goals.

Grit and perseverance have their place. I think those are great attributes to have because that’s what meaningful goals sometimes require.

So when it comes down to choosing action that you know, deep down, is a waste of time, versus feeling like you’re not doing enough, you are likely to choose the former, lest you think of yourself as a lazy person who just can’t get it together.

Let Things Unfold

But, taking action and not doing anything at all is a false choice. There is a way to do things without forcing it.

Imagine dropping some leaves into a river. They’ll all flow generally in the same direction, but they may end up in different spots. Some will get caught on a rock, others nested in the bank, others may make it to the ocean.

Your efforts should be like those leaves. You try things and, without psychological attachment let them go where they naturally want to go. It’s effort plus openness.

You don’t try to force a leaf to move upstream. It’s pointless. If you’re encountering so much resistance, that’s a sign you’re trying to move upstream.

The metaphor is limited, but here’s what not forcing it may look like in a job-hunting situation:

• Having lots of conversations with people and sharing your situation (a more honest version of networking) but also sharing your natural interests

• Working on an interesting side project that may have professional applications

• Taking some part time or gig work to pay the bills while you keep your eyes out for opportunities

• Finding companies you’re actually excited about and pitching them ideas on how to help them

This should all feel, if not effortless, at least not like you’re swimming upstream, it should generate a curious and hopeful feeling, like “I wonder where I’ll land.”

You won’t beat yourself up for not doing everything humanly possible with every spare minute you have to get a job.

How I’m applying it today

I’ve been dissatisfied for a long time about my work in government contracting. But whenever I was in between projects, I’d run back to it, instead of branching out. I’d make some token efforts to look at non-government corporate jobs, but I felt repulsed by them. So then I’d go back to the only industry I felt comfortable in. The longer I went in between projects, the more anxious I felt about money, the more embarrassed I felt about not working, and the worse I felt about myself. I’d retreat into myself.

This time I’m dropping a few more leaves into the river, reaching out to others and being open to different paths and outcomes. I’m learning to accept that anxiety is part of it which, helpfully, lessens it.

Accept Being Lost

I felt perpetually lost and dissatisfied in my twenties (and to a lesser extent, my thirties). This wasn’t a bad thing per se. It forced me to take action. I read lots of books, started a few businesses and writing projects, and made some good relationships along the way.

The mistake I made was to think that being lost and dissatisfied was something to be resolved, that the feelings themselves required drastic action and that the measure of success was to feel like I found “the” path and perpetually satisfied.

But there’s nothing you can change about your external situation to make it feel like you’ve solved your existential crisis once and for all.

When you embrace that, you can move through your lives with greater freedom and love. Freedom because you’ve loosened the grip of endless expectations, love because you accept your life as an unearned gift.

—-

As your dad, it’s a real joy to witness your lives unfold, particularly as this very cute stage of your childhoods. I can’t force anything to happen (despite my efforts to get you dressed and out the door), so instead I get the luxury of watching you both become yourselves (unless we’re running late).

If and when you have your own kids, you’ll understand the feeling, but before then, I hope you can learn to take joy in witnessing your lives unfold, even when it feels like things aren’t going your way or aren’t progressing as quickly as you like.

Instead of forcing your life to happen, just watch your leaves of effort float down the river and land where they naturally want to go.

Love,

Dad

Dear Gup and Dabbles,

I’m about 70,000 words into the book I’m writing for you Gup (Dabbles, don’t worry, I will write a book for you next!).

The book is meant to be a sort of life guide to your twenties, focusing on the main areas that I believe are important (career, family, identity, etc).

In the process of writing the different sections, I keep discovering these meta themes about your twenties and life in general that sort of tie all the sections together, so while they’re fresh in my mind, I wanted to distill them here.

• In your twenties you don’t know enough about yourself.

• You also don’t know enough about the world.

• The biggest trap in your twenties is thinking you do know enough about yourself and the world, and then trying to create a life around these false ideas

• The way to fight this trap is to try different things in real life, and then catalog and deeply reflect on how you react to those different experiences.

• Over time you’ll begin to develop a more accurate picture of who you are, and have a better understanding of how the world actually works.

• Once you accept the truth about yourself and the world, you can begin to live freely.

• Living freely means not trying to live a life that is in contradiction with who you are and how the world works. To live freely is to live truthfully, as you see it.

• Knowing the truth does not mean living it is easy. There are many pressures life throws at you that may have you question what you know and believe.

• There is no point, in which you’ll feel like you’re living 100% consistently with the truth. Life is messier than you think.

• The key to a messy life is not to try to chip away at the bad parts and only leave the good parts.

• The key is to love all of it, the good, the bad, and the ugly.

• There is no part of the messy life that is not just part of life.

• The best “hack” to love your messy life is to find a partner and spouse who can support you and whom you can support. Messy lives are more fun if you spend it with someone you love and who loves you.

• Becoming a parent will make your life even messier, but also give you more perspective. The things you think are important and unimportant will change dramatically.

• This is because kids increase your capacity for love. Your heart breaks open and in a way, you become a different person, in a new reality.

• It’s a process of “unselfishing,” a process of removing yourself as the center of your universe.

• Unselfishing is a good indicator that your twenties (conceptually, not literally), are beginning to end.

• You begin to internalize that your life is just a small part of a whole web of relationships, environments, and experiences that represent all of existence, past and present.

• From this new perspective, you can look back at your twenties with gratitude, gratitude for getting you to this place in your life, even if the path felt long and winding.

• Knowing that your past led you somewhere you couldn’t have predicted, you can look forward to the future without expectation, understanding that life will unfold as it wants.

• If your twenties was about trying to understand life and master it, the next phase is about surrendering to it.

Gup and Dabbles, though I’m sharing these insights with you in neat bullets, you’ll only really be able to internalize them by living. When you’re adults, I hope you’ll let me keep watching, listening, and being a small part of those lives you’re building.

Love,

Dad

Dear Gup and Dabbles,

I read this article the other day about young women who feel FOMO on going to the Hamptons because of all the social media content from both influencers and “normal” people. They film their trips there and make it seem fun and glamorous which of course, makes other people want to go there and they spend thousands of dollars for something that was previously reserved for the very wealthy (or perhaps, someone of more modest means who saved for a splurge).

My first thought was, “if you get influenced by this crap, you must be pretty shallow.”

My second thought was, “hmm, I’ve gone out of my way to sign up for maybe a hundred credit cards because of points bloggers who made me want to fly first class for free.”

My third thought was, “am I actually just as gullible as these Hampton’s people?”

Then I thought I should write a letter to you both to work out my thoughts on this, because the world is going to try to influence you, and I want you to be smart about what you let yourself be influenced by.

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Let’s start with my biggest fear: that you fall into the wrong crowd and start doing things that can hurt you.

Drugs come to mind. If you run with a crowd that normalizes that behavior, I worry that you’ll take something that will kill you. It may seem cheesy or something that doesn’t really apply to people who grew up in middle to upper-middle class families.

I read an article about a few normal professional types in New York who ordered delivery cocaine (I guess in NYC you can get anything delivered…) and died because the cocaine was laced with fentanyl.

Apparently cocaine is a somewhat normal part of high-achiever culture in NYC. I’m sure when these victims were in high school they didn’t envision dying of an overdose or making cocaine a part of their lives. But maintaining a high stress, high pressure career led them to believe they needed drugs. And maybe they did. One of the guys in the article was a Wall Street trader who probably worked 100-hour weeks. I don’t know how you do that without some kind of drug.

But this is where I hope you take some of my fatherly advice. If you are pursuing something that requires you to take drugs, or really, do anything that is so obviously risky to your health or life, you should re-evaluate your goals.

This seems obvious but I imagine it’s easier said than done. If you dreamed of becoming a top tier New York lawyer or investment banker or [insert other dream job] and you actually got there, you would probably go to great lengths to not lose it. Giving up something you worked hard for and that you love will make you do crazy things, like starting a cocaine habit.

Avoiding these types of tragic goals is probably the preferred strategy. If someone told these guys they’d have to do cocaine to get their dream jobs while they were kids, they probably would have done something else.

But you’ll inevitably be in a position where you might have to give up on something that’s become a part of your identity, your self-image. That’s when it’d be hard to walk away and you might try negotiating with yourself. “Well, if I can just get through this tough period at work, I’ll stop the drugs and get healthy and really make some changes.”

But it will never happen.

I don’t have a good solution or technique for walking away from a part of yourself, but there is a lot of ancient wisdom about attachment and how holding onto things too tightly can corrupt you. You basically get greedy and cling to what you have.

You could be greedy in the traditional, material sense. For many, a little coke is a small price to pay to live in a nice apartment in Manhattan.

Or you might be greedy for a vision of yourself as someone who will do anything it takes to do good in the world. One of the women in that article was a social worker who counseled cancer patients. She witnessed a lot of suffering and did her best to help, but perhaps to sustain this career (and therefore her self-image), she needed drugs to help manage the emotional energy expenditure.

Now to be fair, I’m guessing most social workers and Wall St. traders don’t do cocaine (though I’m less confident about the latter), but the slightly more normalized culture of cocaine use in NYC made it easier for the young people in those articles to feel okay about trying it, which of course led to tragedy.

I went on a bit of a tangent with this whole cocaine thing, considering I opened the letter about some silly Hamptons influencers. The chances of either of you dying via fentanyl laced drugs is pretty low, statistically speaking. It’s just my dad brain that watches out for these very overt threats.

But it’s not as much of a tangent as it may seem. The NYC cocaine story is about how how an extreme behavior can become normalized in the culture, occasionally leading to tragic outcomes.

The upside is that it’s observable, so you can avoid the threat. You know drugs can kill you, so don’t do drugs and don’t pursue things that would subtly pressure you to do drugs.

But there are lots of hidden cultural pressures that are much harder to detect that are also harmful to your well-being. They just shape you without you knowing it. It’s like having poor eating habits. No single day of bad eating really matters that much, but a decade of it can lead to health problems that you just accept as normal. You didn’t even notice you were making yourself sick.

Your aunt Chloe came to visit us here in Arlington, VA this week. She has lived in Portland almost her entire life, and she made a comment at your [Gup’s] pre-school graduation and birthday party that all the parents were extremely put together, organized, and wealthy. This was in contrast to Portland where the population basically self-selected for it’s creative/slightly slacker ethos.

Her comment made me feel a little proud to live here. But what she doesn’t observe is that the DC crowd, on average, are very career focused, stressed, and a bit trapped by upper middle class golden handcuffs.

I asked some of the dads from your pre-school at a happy hour the following question: if all careers paid the same, what would you choose to do?

No one chose their current career.

But lots of people don’t like their careers. What was interesting is that none of them mentioned making any serious efforts to change it. They basically accepted that they needed to make a certain (high) amount of a money, make sure their kids go to excellent schools, and buy a nice house in a reputable neighborhood. Their values were shaped by the DC culture, which prioritizes career success above all else. Or, more accurately, a successful career is a minimum requirement to be here.

What happened to my DC parent friends is just the more, subtle, long term version of what’s happening with those women who have FOMO onHamptons trips. You start wanting and believing what your peers (or perceived peers) want and believe, even if you don’t actually want or believe those things.

You don’t have to be particularly gullible, it’s just the way humans are wired.

But you are my daughters, and naturally I want you to be happier and more fulfilled than the average human, so I want you to become cautious observers of the cultures you participate in. If you get good at observing the values underlying the culture and groups you are a part of, you can make a conscious decision about whether to adopt or reject them.

Your mom and I are wrestling with the cultural values we want to accept or reject right now. We’ve seen the good and the bad of our zip code, and on the surface, it’s mostly good. But something keeps calling us elsewhere and it’s really hard to pinpoint.

We like people with ambition so DC seems like a good place to be but we also like people who have unique ambitions, so Portland seems better for that. We also like good coffee and Portland is way better for that but DC also has all the jobs while Portland seems to get by on part time barista work and dreams.

We haven’t reached any decisions which is why we’re still here in the DC area, but I feel good about noticing the tension and contradictions in our values. That’s the skill I want you both to cultivate: to identify the values of the cultures you’re in and the feelings you have about them.

And to say no to drugs, and not get in credit card debt to go to the Hamptons.

But mostly the values thing.

Love,

Dad

Last week I had a call with a 25-year old kid (yes, I can call 20-somethings kids as a thirty-something dad) who decided to quit his job at a private equity firm, move back home with his parents, and buy a business.

He decided to quit because he was working non-stop and saw that his boss and his boss' boss also worked non-stop. He knew it would be intense when he joined the company but he felt it deeply when he had to work during his PTO while visiting his newborn nephew.

To make matters worse, despite a glowing performance review, the company passed him over for a promotion that he was implicitly promised.

The future payoff was not worth the grind, so he crashed his life and quit.

---

The first time I crashed my life was about six months after I graduated college. I had commissioned into the Navy and won a spot at BUD/s, the initial selection training for aspiring Navy SEALs.

It wasn't long before I realized I didn't fit in. I was below-average performance wise, I didn't relate to most of the officers there (and wouldn't choose to hang out with them), and most importantly, I was no longer excited by the prospect of becoming a Navy SEAL

I set a goal in high school of becoming a Navy SEAL, and took all necessary steps to get a spot in training. But between high school and the time I entered training, that desire had faded.

So I quit, and then six months later, I was out of the Navy entirely in the middle of the Great Recession.

Crash.

---

I asked Jake (the 25-year old) why he wanted to buy a business as his next career move.

He listed a few:

• He wanted more autonomy and control over his destiny

• He wanted to take the risk now while he was young and not thirty-something with a family

• The potential to make a lot of money was appealing

• He likes the idea of creating a great service experience for customers and wants to really make them happy

I thought these were all great reasons for buying a business, but just to be a bit of a provocateur, I asked:

"Have you ever considered moving to Thailand for a year and screwing around?"

---

The reason I asked this question is because after I separated from the Navy, I went to Cairo with your mom to teach English to have an adventure. I was newly under the influence of Tim Ferriss' Four Hour Work Week and wanted to live cheaply overseas and think of a "passive income business" I could start.

I made a complete 180 degree turn in life paths. Initially I was on track for a military career, and now I was on track to live a very strange unstructured, bohemian traveler lifestyle.

It would have been relatively easy to change course in a less dramatic fashion (say, a 30 degree course correction) by say, pushing harder to find a different military career path, maybe leaning into an intelligence officer career.

The 180 degree turn was valuable, but not because living overseas full time or starting a passive income business was the right path for me.

It was valuable because it gave me more information about myself. My self-identity had been built around pursuing this Navy SEAL goal and I destroyed that in under a year. Trying to pursue a different military career would have been a sort of compromise solution. I'd still be doing something masculine and patriotic inside a bureaucratic organization with a defined career path and sure I'd learn a few things about myself.

But I wouldn't have gotten so many insights into myself as I did hanging out with a bunch of American expats and wealthy western-education Egyptians and trying to start my own business.

I learned that I chafe under authority (wish I had known that before joining the military), I have a creative side, I default to laziness in the absence of work, and I appreciate developed western country comforts,

I learned that I'm actually not particularly money motivated. I like being contrarian. I learned that I was confusing wanting to be an entrepreneur with wanting to be known for my ideas and making money outside of a paycheck format.

I learned a lot, and I learned it on an accelerated timeline, because I did something so radically different from what I was initially doing. These lessons are still making a big impact on how I think about my career today, now that I'm a thirty-something with a family.

---

Jake was surprised by my question, and he responded, honestly, that no, he has never actually considered doing that.

And I don't think he will.

I think Jake will be just fine. Buying a business is definitely an adventure.

But it feels a little too close to what he was doing before in some ways.

It's still business and money driven to some degree. It's still analytical, and it's still a known and well trodden path that can be prestigious if it works out. I think it's a 30 degree correction, not a 180.

Jake will still learn a lot, but my hunch is that he'd learn a lot more about himself if he actually went to Thailand (or other cheap foreign land) and tried not having any goals for a while.

---

One of the best ways to learn who you really are and what you truly want is to experience something completely different from your default path [see ’s writing on this].

Career crises, despite being painful, are uniquely valuable moments that make radical experimentation possible.

My advice to you, sweet daughters, is that if (or when!) you face a career crisis, don’t rush to simply fix it or get back on a known path.

Instead, ask yourself: "What is the most interesting, radically different thing I could try right now?" And then go do it.

Like Jake correctly assessed, this is the time in your life to take risks.

Just make sure you're taking enough risk to make it worth it.

Love,

Dad

This morning I completed a four mile run, at a pace of 9:00 minutes/mile.

In the not-so-distant past, I would have berated myself for running so slow because when I was in high school, I was pretty fast.

I wasn’t elite by any means but I ran track and cross country. My mile time was 5:07 and my 5k time was under 18 minutes. I felt proud of myself.

I carried this identity of being an in shape person (with abs!) for a long time

This identity was useful, because it kept fitness and physical health top of mind. Even if I wasn't always consistent about working out, I felt BAD when I didn't and so would never go too long between workouts.

But as you get older, your life fills with more constraints.

In high school, you basically have zero major responsibilities. In college, it’s pretty much the same. Perhaps after college when you get your first job you have limited hours to work out and it requires some light tradeoffs.

Since I became a dad, there have been real constraints. Kids (and by kids, I mean you two) demand a lot, and more importantly, they are disruptive to any sort of consistent planning.

Even if I'm disciplined and can get up early to workout before work, if either of you started crying in the middle of the night, I’d be too tired to do the 5 AM workout.

Because being in shape is part of my identity, my instinct is to berate myself for not maintaining discipline or being tough enough to push through the fatigue.

But this is just my identity trying to fight reality.

The problem is reality always wins, but you can be in a state of denial about this for a long time.

The key then, for all identities that you want to continue to maintain, is to approach them with the attitude of "strong identities, loosely held"

The identities stay strong because you’ll always retain them to some degree.

But holding them loosely means being aware of the very real constraints you have, and then adapting your identity to account for them.

In my case that means accepting I won't be able to work out as frequently as I want, that I might have to let go of my abs, and that I'll have to move up a pants size, at least for a little while.

But I still view myself as a fit person. That will prevent me from totally going down the dad-bod mode route.

As you go through your twenties, you should keep tabs on these open identities you have.

The classic cliche is the former high school football star or prom queen that peaked in high school so they cling on to their glory days, never allowing themselves to move on.

But identities can be subtle and nuanced.

Here's another one of mine that is more subtle: "rational guy."

Since high school I've always viewed myself as a logical person who could reason my way through things to solve problems and navigate life.

But this identity as a rational person has been breaking down, and has in fact, blocked me from being more fully human

For example, for a long time I thought my frustration with government work was that it was inefficient and ineffective. The government did a lot of things that didn't make sense logically for the aims it was trying to pursue.

But it turns out a lot my frustration stems from people (i.e. clients) telling me to do things I didn't want to do. It also turns out that these conflicts are just me psychologically re-enacting some of my childhood fights with my dad and adding a "logic" based explanation for what I was feeling.

Since I've acknowledge this reality, the frequency and intensity of that anger has reduced, and I've become more aware of how my emotion drives my thinking.

So sure, I'm still probably more rational than the average person, but I also have the full range of emotions that anyone else does.

This realization has been a bit of an epiphany in terms of being able to see more possibilities for myself in all domains of my life.

By loosening my grasp on this “rational” identity, I've been able to incorporate my feelings into my behavior and decision making.

There's a biblical lesson from I Corinthians 13:11 (KJV): "When I was a child, I spake as a child, I understood as a child, I thought as a child: but when I became a man, I put away childish things."

This is a lesson in maturity, but I think we can adapt it a bit. Instead of just putting away "childish" things, we can say, "when I became a man, I put away closely held parts of my identity that were no longer true nor serving me."

Not as pithy, but you get the idea.

Clinging too tightly to any identity is going to hinder you. Your twenties are a great opportunity to practice loosening your hold on your identities.

You don’t have to keep pursuing STEM careers just because you were good at high school calculus. You can pursue art if that’s something you want. You don’t have to let your superior math skills dictate your direction in life.

If you were lazy in college it doesn't mean you can't work hard now to get something you want but thought was out of reach because of your work ethic. You can tell yourself a new story declaring yourself to be a hard-working person who puts in the effort when it matters.

Learning to evaluate and loosen your grasp on your identities is a great skill to have. It’ll help you grow, stay sane, and even find joy in the chaos —especially when the chaos has names like Gup and Dabbles.

Love,

Dad

It's Q2FY25 in government fiscal year time and Elon Musk's DOGE (Department of Government Efficiency) is in full force, cutting or threatening government employees and government contractors with termination.

---

I've been working in government contracting and have run my own government contracting business for over a decade now, and I've mostly disliked it.

Sure, the money has been good and on occasion I have fun tinkering around in Excel, but for the most part, my position has been, "God I can't believe this is my professional life."

So last month, I made a plan to quit. By the end of the summer, I will leave the day job of sitting around at a government office not doing anything important to pursue...something else, something more creative and fulfilling.

I didn't arrive at the decision easily. It took a lot of careful thought and introspection. I even hired a coach (thanks ) to try to help me NOT quit!

But I arrived at the inevitable conclusion that I should quit, and I felt really good about that decision.

---

A few days ago, my business partner texted me and said his programs might be at risk of getting cut by DOGE.

This triggered some fear in me and my gut reaction was to hold on to my project for as long as possible.

This was strange because I was ALREADY PLANNING ON QUITTING!

DOGE making some cuts to our business would have minimal impact on me if I quit.

But still, the feeling was there.

---

Part of working through the decision to quit was learning about a form of psychotherapy called Internal Family Systems, or IFS.

The core idea is that everyone has these "parts" that represent different parts of their psychology and identity. Some broad buckets for these parts include managers, who, as the title suggests, tries to keep you safe by managing your environment, behaviors and emotions. Firefighters are sort of emotional emergency workers that take dramatic action to guard you against painful emotions. Exiles are sort of inner child personas that have had some sort of painful experiences or trauma.

None of these parts are bad. They serve a purpose. But they can become imbalanced or come into conflict with each other.

In my case, it literally felt like my manager part was in an interminable war with my firefighter part. My inner manager wanted to protect me from financial stress and generally, blowing up my life. My firefighter wanted to extract me from the soul deadening environment of a government gig immediately and send me off to the woods to work on my novel.

Both parts sounded totally reasonable. Well, the firefighter did not sound reasonable, but he certainly sounded fun!

But this war in my head was driving me insane, until I realized that it was a war between those two parts.

Once I acknowledged them, I negotiated a peace-treaty that involved quitting, but with some time-bound constraints.

I felt at peace. I was letting my true "Self" lead, which is the core soul/identity/ego matter that defines who you really are.

---

Having that IFS experience, I quickly realized that my inner manager was feeling threatened again and was just making itself known. It felt threatened because instead of being able to say, "you can't fire me, I quit!," DOGE was going to fire me first such that the inverse was true: "I can't quit, you fired me!"

I once again, acknowledged the manager, thanked it for remaining vigilant, but reassured him our original peace treaty still held, and I felt better.

--

In your twenties (and beyond), you're going to feel conflicted in many domains. Are you going to be practical and take a steady job or take a wild risk and start your own business? Do you follow a boyfriend to another city where you don't know anyone or stay in your hometown?

There are lots of decision-making frameworks out there that could be useful. At a basic level, a pros and cons list, or, if you want to be a consultant nerd about it, you can run a SWOT analysis

But my hunch is, the really hard decisions you have to make, the ones where you decide choice A one day and choice B the next, come down to conflicts between your different parts.

All the parts are trying to help you, but they are also driving you crazy, and making you feel insane.

I want to assure you both that you're not insane, and that there is a way to let your true Self lead.

First, you need to acknowledge that you have different parts and be able to identify them.

I didn't go to therapy, but I read a book about IFS and did a lot of writing and bounced some of my experiences off of ChatGPT.

I identified my manager part and firefighter part when ChatGPT spit out a description of each them that aligned with my thought processes and feelings.

It was a feeling of "oooh that's definitely the manager right there."

Next, once you identify them, you need to thank them for doing their best to help you.

You shouldn't despise them and wish one part would just disappear. IF your manager has been dominant you might resent the firefighter for trying to make you take dangerous risks. Or you might resent the manager for not letting you take enough risks.

But the manager (and the firefighter) was doing its best and you needed them at some point in your life. So thank them.

Finally, you should imagine yourself taking different courses of action and seeing how your gut feels.

For me, I felt a strong agitation and restlessness when I thought about just trying to stick it out in my job. Obviously, my firefighter was acting out.

But when I thought about quitting, my manager would freak out and get me worried about things like 401ks and becoming homeless.

When I thought about quitting, but in a few months instead of immediately, I felt a great sense of relief, like that was exactly the right decision.

When you feel that relief, the true Self has spoken.

----

My wish for both of you, my sweet daughters, is that you don’t spend your lives feeling trapped between competing voices, unsure which one to trust. I want you to know that you are whole, that you have a Self (Selves?) that is wise, calm, and strong enough to guide you through anything.

And of course, if that fails, your wise ol' man can just make your decision for you.

Love,

Dad

PS: Don't follow the boyfriend to a new city, particularly if he has lots of tattoos.