#106: Avoiding Hustle Traps, Squads, From Politics to Seminary & More

😷 Making sense of what matters in these crazy times

September 5th, 2020 - Greetings From Connecticut!

This is my last week in Connecticut as my wife and I are about to embark on a road trip across the US via North Carolina, Boulder, Utah and Phoenix to LA before heading to Puerto Escondido for the winter. If you are somewhere along the route or would like to camp with us, let me know!

This was a picture of my wife and I spending some quality time with my grandmother!


#1 Avoiding Hustle Traps: The whole game is to keep doing what you want to be doing

My conception of the self-employment “game” has evolved to be defined as creating a life that I want to keep living. This means that work is downstream from life decisions. Compared to how I was living until I left my job in 2017, this has been a dramatic shift and one that comes without a map.

The biggest challenge is not making money, thought that is certainly hard. It is learning to be comfortable with uncertainty and knowing how to exist in a state of not knowing.

This is incredibly hard because at almost every step of the journey, there are tempting actions to take that will enable you to escape the weight of that uncertainty.

Let’s talk about six of these “traps.”

#1 The dopamine bomb of internet fame

I think its still early for creating on the web. If you are able to consistently create content, explore topics you are genuinely interested in and develop some way to improve as you go, you will inevitably get some version of 15 minutes of internet fame. This could come from a famous person promoting your stuff, getting published in a mainstream publication, economic success or or some piece of content going semi-viral for a few days.

To the self-employed creator that dances in daily uncertainty and self-doubt, this can unleash a satisfying dopamine bomb of approval. This can be so blinding and exciting that you might try to chase that same feeling over and over again, even if its not the work you actually want to go deeper on.

I got a dose of this when I posted a Twitter thread exploring the “40% of Americans cant afford a $400 emergency bill” myth. If you read the report and the data, you’d be doing some serious mental gymnastics to land on such a takeaway. However, I was looking at it from the perspective of a former consultant who is skeptical of how data is represented and didn’t realize I was walking into a political talking point. This exploration earned me the applause of right wing trolls and a twitter follow from Ann Coulter.

That wasn’t a path I wanted to keep exploring.

#2 The desire to prove yourself, especially to your parents

In my conversations with people around the globe, the biggest challenge many self-employed creators have is winning the approval of their parents. This is often unspoken, but can drive a large amount of decision making of people wandering into the self-employed space. Being self-employed in the digital world is a life that is illegible to many in our parents generation and I’ve seen a lot of people quit without giving it a proper chance or not fully pursing things they might be good at.

It’s often easier to do things that win us approval than doing the things we really want to pursue.

Stephen Warley, who has become a friend and mentor, has been self-employed for almost the last twenty years, but says it took years before his mother accepted his path. Once he came to terms with the fact that the approval may not come, he was able to move forward.

4 years in, I was struggling and I was talking to my mom one day and she asked if I would ever consider getting a job.

I told her absolutely not and I haven’t struggled since!

#3 Trying to recreate the success of a guru

A great trend online has been that many people who have reached some measure of success are very open with their approach. This can include sharing writing strategies, audience building strategies, pricing tactics, content creation strategies and so on. The depth of information available to people who want to follow certain paths is more honest and useful than ever before.

However, many people mistake the tactics for the journey and overlook the more challenging things like the inner game, managing finances and navigating relationships that enable people to succeed.

Ultimately you can only learn so much until you need to do things in your own unique way. Robert Greene outline three steps of learning through apprenticeship in his book Mastery.

  1. Passive Mode: Learning the rules of the game and how it works

  2. Practice Mode: Taking action & building skills

  3. Active mode: Experimenting in your own way

As Greene says about the active mode,

“most people wait too long to take this step, generally out of fear…you must force yourself to initiate such actions or experiments before you think you are ready"

I think most people follow or seek out gurus way too long. Instead of looking for the next course or playbook, try to do things the way you want, even if it doesn’t feel right.

#4 The productivity trap / Streak trap

Growing up in the US is to be convinced that your purpose in life is to continuously be doing things. To rest is to be lazy and to avoid feeling lazy its smart to keep doing things.

It’s a great idea when you first start creating to commit to some type of rhythm, such as posting once a week, because this can help you overcome a lot of the self-doubt and friction that emerges when you first start sharing online.

Over time this can become a trap or a way to avoid the deeper reflection to keep your journey alive. Or as Anne-Laure Le Cunff, who has written a lot about the traps of productivity, an avoidance of the questions that matter:

We are scared of idleness because stopping would mean having to really consider what we want out of life and what we currently have. Sometimes, the gap feels so wide, we’d rather stay on the hamster wheel.

The way I see it, work is downstream from life. It’s always hit me as a bit absurd that people describe their Sundays as “unproductive” if they fail to do laundry and some chores.

When you are self-employed you definitely need to find some way to motivate yourself, but often people mistake the productive urge for the thing that keeps them going.

When you create deadlines that stress you out, remember that you are the one tuning self-employment into a job and isn’t the whole point of self-employment to avoid having a boss telling us what to do?

So I give you permission to take a week off. If anyone gets mad, blame it on me.

#5 An income goal as the metric of success

Nothing will force you to compromise quicker than lofty income goals for your self-employed life. In my first year of self-employment I used my freelance target income calculator and figured out that if I’m living in the US, I could pay for a life I really liked for about $35,000-40,000 in earnings per year.

This required a year of testing my limits after living in a high-end apartment in New York City, but it also helped me to be able to say no to many paid projects in that first year. Instead of those paid projects I developed things like Boundless, the Reimagine Work podcast and my future of work mindset assessment.

If I had an income goal of making $100,000 a year I would not have pursued this path. But I had not defined my own success as an amount of money. My metrics of success were closer to what Thomas outlines here:

Money is important but most people tend to overvalue the importance of money as they start their self-employed journey and undervalue the unexpected upsides of more flexibility, space for creativity and leaving time for unknown opportunities to emerge.

#6 The “I am a x” identity trap

You used to have an easy answer to the “what do you do?” question. Now you find yourself mumbling random lines about making friends on the internet and writing 25 blog posts about an obscure topic you’re fascinated by and you get hit with blank stares.

This can make a lot of people desperate to have an easier to understand label.

There’s a subtle different between adopting labels to increase legibility to potential clients and seeing that label as who you are. It makes sense to tell potential clients you are a freelance consultant, but if you start seeing the world through the eyes of what a freelance consultant might do and looking at others freelance consultants for what kind of work to do, this might be a trap.

You are a human playing the role of a freelance consultant. Always remember that and your game will be a little more fun.

A New Post-Hustle Narrative Emerging?

When I started sharing publicly online a few years ago, the dominant narrative was a hustle narrative. Do as much as possible, as productively as possible. This works for some people but I think is a trap for most people and at worst, locks many in a cycle of performative productivity instead of exploring what they want to do.

I think a lot of this comes from fear, as Anne-Laure argues:

Going deeper, consuming too much productivity porn can sometimes be a symptom of lack of confidence. The process of learning from supposedly more productive people is akin to asking for permission to start working on an ambitious project

The only way to gain confidence is through the discomfort and finding things you actually want to create. It doesn’t make sense to create 100 podcast episodes if you hate podcasting. Find a better avenue or take a break and see where your energy goes.

Michael Ashcroft shared a similar sentiment from an emerging counter-narrative to the productivity driven mindset that so many self-employed creators gravitate towards.

I’m not sure “non-coercive productivity” is the right term but it gets to the heart of the challenges that emerge when we ignore the traps of self-employment and creating online.

It’s time to stop talking about productivity and start talking about the work that matters to people.


#2 Squad Culture - A New Millennial Mood?

I loved this essay on “squad wealth.” It seems this whole pandemic pause has paused a lot of young people to look around and realize they want a bit more than the work-centered individualism that the economy has nudges us into:

Squad culture is the antithesis of neoliberal individualism. Millennials are healing from decades of irony poisoning, rediscovering what it's like to have generative, exploratory relationships with one another. Younger generations are already imbued with extremely powerful squad energy, equipped with formative experiences in Minecraft, DOTA 2, and Fortnite parties.

Great read, check it out here.


#3 The Ugly Truth About High Wage Cities

The hidden truth about the incredible boom time for high-wage workers in expensive cities has been that these cities have increasingly relied on a lower-wage precarious class of workers that service these high wage workers:

But now, suggests MIT economist David Autor in a paper last month, the office economy is under threat. The pandemic, he and his co-author, Elisabeth Reynolds, a lecturer at MIT, write, has made a permanent shift to remote work for a large part of the office workforce a near certainty. And with that, tens of thousands of workers in the office support economy — those who “feed, transport, clothe, entertain, and shelter people when they are not in their own homes” — will lose their jobs.

This has served a pseudo wealth redistribution, especially in places like New York where people in service industries can make a decent living. But now many of these jobs have disappeared and I’m not sure they’ll ever fully come back.


#4 Worker Reclassification

There has been a steady trend of worker re-classification of middle wage jobs over the past ten years that I first came aware of in this Politico article on the real future of work. These are the kind of jobs that have made having work beliefs like “work hard and you’ll be okay” a sensible idea as a way to navigate life.

Unfortunately, companies don’t care about work beliefs. This essay about Vanguards decision to turn 1,300 full-time employees into contractors is an ongoing trend to watch.

But “Vanguard employees who will be re-badged as Infosys employees better start looking for new jobs as soon as possible because almost all of them will be let go after the 12-month commitment expires,” predicts Howard University associate professor Ron Hira, who has studied “offshoring” and foreign tech worker visa programs since the early 2000s and testified in Washington on the impact of the H-1B visa program on U.S. workers.

Hira adds:

“The stock market is doing well. Vanguard is doing well. Why is it offshoring all of these middle-class jobs? Why didn’t it invest in its workers?” Hira concluded. “This is a microcosm of what’s wrong with the economy.”


#5 Laving A Path That Makes Sense

From the Life I Want, a great site by Christine Bader, this interview with Cyrus Habib, the former lieutenant governor of Washington resonates with many of the stories I’ve heard of stepping off the default path.

He left a promising career in politics to join a seminary:

I came into politics and that started to happen to me. I started seeing myself playing into it and being like, “O.K., let me get a book deal; let me try to get a national speaking role at the convention.” I started seeing myself wanting that without ever asking myself the question, “What do I want it for? Would that make me happy?”

and some interesting thoughts on work, identity and living fully:

This is why I think about vocation more broadly, because I think your marriage and your kids and these kinds of things are also vocations that you have. If those play a proper role in your life, then your job becomes a job and you take it seriously, but you don't take it too seriously; it doesn't become central to your sense of self worth.

The second thing is, do you truly feel comfortable with what you're doing? If you lost your election or you got fired from your job, would you be fine? Would you be happy with what you did and what you would be able to do next? Or do you need this? And in fact, do you not only need this, but do you need what comes next? That can be distortionary.

Where I see holiness is in someone fully—and I think the Dalai Lama is the apotheosis of this—fully living in the moment, the self that they feel they’re meant to be, and for whom what they do therefore becomes a joy. Because it’s not pointing to some other reference: It is itself where one is meant to be.

Check out the full article!


🎧 New Podcast! If you wanted to listen or watch the conversation with Amy McMillen about writing a book and how she handled taking a year wandering into the unknown, check it out via Reimagine Work or youtube link here:

Thanks for tuning in. See you next week!

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