Check your Pulse #49

Letter to a friend who is thinking of leaving her job to do do something on her own

Welcome to the 631 subscribers since the last issue. I’m Sari Azout and this is the the 49th edition of Check your Pulse, a tech and startups newsletter designed to make you feel human. I try to make this one of the best emails you get each week. If you’ve been sent this email and you’re not a subscriber, you can join by clicking on this big red button below.

Happy Tuesday, friends.

It’s been a while since I popped into your inbox.  

Truthfully, I’ve tried dozens of ways to carve out time and energy to write. Turns out, no amount of coffee can help me parent two wonderfully exhausting children, run a fund, work on ongoing consulting projects, this newsletter, and a side project all at once. And it turns out, I’m not alone.

I can’t promise a consistent cadence, but I promise that when I write it will be worth your time. Respect for your time is my #1 priority. 

Today’s issue is a little different. A friend who is thinking of leaving her job to do something on her own recently asked for my advice, so I wrote this letter. As I crafted these thoughts, I realized they are relevant to anyone considering leaving their job to pursue a passion.

I know you’ve been thinking about doing something on your own. 

There are a lot of resources to draw upon to help you find product-market fit. There are less resources designed to prepare you for the psychological challenges.

The passion economy promises to bring greater alignment between your life and your work. And yet, in the passion economy, the real risk is that your job has to earn a living and meet the needs of your soul.

As you let the possibility of merging your career and your passion live in your mind, I’ve tried to distill the patterns that I’ve observed into a series of questions:

  1. Will you use this opportunity to grow and evolve or will you use it to beat yourself up?  

  2. How will you avoid insecurity work?

  3. Can you learn to enjoy the process as the end in itself, not the means? 

  4. Will you default to the norms of your industry, or will you be an original?

  5. What tools will you use to quiet your ego and see reality clearly?

  6. Do you have clarity on what kind of financial value you aim to create?

Will you use this opportunity to grow and evolve or will you use it to beat yourself up?  

Ideas start out small, weak and fragile. 

In order to grow, ideas need financial capital. 

But they also need emotional capital — good energy, positivity, and resilience. The best way to control your emotional capital is to fine tune your internal monologue and replace your hunger for approval with a desire to grow. 

Jeff Bezos has a wonderful quote about this: “Invention requires a long-term willingness to be misunderstood. When you do something that you genuinely believe in, that you have conviction about, for a long period of time, well-meaning people may criticize that effort. To sustain yourself over this time, you can’t look for accolades, and you can’t rely on being understood.”

The only remedy I know is patience. 

Stay the course.

How will you avoid insecurity work? 

When you’re anxious, there is no quicker relief than checking things. Checking your Substack subscriber stats, refreshing your inbox and order confirmations.

Scott Belsky coined the term insecurity work to describe work that does not move the ball forward, but is quick enough that you can do it multiple times a day without realizing.

Unlike insecurity work, deep work often feels elusive because it takes time.

It requires weaning yourself from distractions and being unencumbered by the highs and lows of the day to day.

Your ultimate objective is to ride the waves of your business with serenity.

Can you learn to enjoy the process as the end in itself, not the means? 

In the beginning, the dissonance between the scale of your aspirations and the reality of your days will riddle you with anxiety. You will be tempted to strip the unknown of its surprises and travel to the future: What if my customers churn? What if a competitor introduces a better product? What if I run out of ideas? 

But spending your time wrestling with the future is an invitation to ride on the envy trolley, to look at another’s peaks with jealousy and end your days in sadness.

Joseph Campbell’s words ring so true here: “If you can see your path laid out in front of you step by step, you know it's not your path. Your own path you make with every step you take. That's why it's your path.”

Looking back won’t serve you. Looking above won’t serve you. The trick is to look ahead, like a biker riding into the sunset, with lightness, excitement and humility.

Will you default to the norms of your industry, or will you be an original? 

Your business exists in the context of a marketplace, but also in the context of your lived experience.

Defaulting to the norms of your industry will shape your business to be similar to the rest, where the best entrepreneurs zero-in on their self expression. Do you have an eye for good design? Inject design into a tasteless industry. Do you have a knack for writing? Share your journey and commit to learning in public. Are you funny? Inject humor into your copy.

You have to be willing to overcome the defaults and orient your business around the things that define you, all the way down to your KPIs. The things you measure should reflect the things you value.

When you’re feeling small, remind yourself this is the artist’s struggle and find comfort in Anna Quindlen’s words: Once you've read Anna Karenina, Bleak House, The Sound and the Fury, To Kill a Mockingbirdand A Wrinkle in Time, you understand that there is really no reason to ever write another novel. Except that each writer brings to the table, if she will let herself, something that no one else in the history of time has ever had. And that is herself, her own personality, her own voice.

What tools will you use to quiet your ego and see reality clearly?

In fear mode, your brain will bend reality to meet your prior experiences and vulnerabilities.

You have to free your mind of the narrative that the world is out to get you, and notice the difference between imagination and reality. When you catch yourself saying “nobody likes my work”, witness your thoughts and replace them with “I am struggling”.

I’ve found a useful way to develop a relationship with the truth is to step out of yourself and consider your circumstance from a cosmic perspective.

Do you have clarity on what kind of financial value you aim to create?

Do you have enough savings to sustain yourself during a ramp up period? If it takes longer to ramp up, how will you gain financial security? Is your significant other on board? Will 1,000 fans paying $10 a month satisfy you? Is your goal to build a sustainable business or are you willing to spend 10 years building a business on a lottery chance to take it public? Are your financial goals truly yours or are they borrowed from somebody else?

I love this quote from marathoner Dick Collins: “Decide before the race the conditions that will cause you to stop and drop out. You don’t want to be out there saying, ‘Well gee, my leg hurts, I’m a little dehydrated, I’m sleepy, I’m tired, and it’s cold and windy.’ And talk yourself into quitting. If you are making a decision based on how you feel at that moment, you will probably make the wrong decision.”

Friend, I hope you can see that what will propel you to thrive has a little to do with your skills and a lot to do with your mind.

I hope you get to know your inner world. I hope you thrive financially while living your values. I hope you focus less on what you achieve and more on who you become. I hope you learn to be kind to yourself. I hope you fall in love with the process. I hope you see the point of pursuing passion work is not to drain yourself to create work that eclipses your life, but rather to create a life you are proud of. I hope this new venture takes you far away from conformism and enables you to make a life and a living on your own terms, with your spirit and creativity unhindered.

And I hope you share your journey so you can inspire me. Because I, too, have been thinking of doing something on my own.



If you know someone who would benefit from reading this, share this issue:


A great list of the best single operator newsletters, featuring yours truly. (Thanks, Eli!) ✍🏻

What a smart approach to marketing Iceland! 🏞️

Michelle Obama interviews Barack Obama in her new podcast! 💯

So much wisdom in this podcast interview with Charlie Songhurst, former head of strategy at Microsoft. I love this line: If you survive long enough, maybe greatness eventually becomes you. One of the things I think that sort of is perhaps underestimated, is if you want to live forever, maybe don’t start thinking about studying centenarians, instead, work out how to not die of a DUI or drunk driving or anybody else smoking 20 cigarettes a day. 💭

This is funny. 😜

With $30bn in GMV, Shopify surpassed eBay last quarter $30bn. 😮

Jeff Bezos’ written statement for the anti-trust committee is a great piece of writing and storytelling. At Amazon, customer obsession has made us what we are, and allowed us to do ever greater things. I know what Amazon could do when we were 10 people. I know what we could do when we were 1,000 people, and when we were 10,000 people. And I know what we can do today when we’re nearly a million. I love garage entrepreneurs—I was one. But, just like the world needs small companies, it also needs large ones. There are things small companies simply can’t do. I don’t care how good an entrepreneur you are, you’re not going to build an all-fiber Boeing 787 in your garage. Our scale allows us to make a meaningful impact on important societal issues. Our scale allows us to make a meaningful impact on important societal issues. 🛒

An important read on cancel culture, contamination by association, and bogus “safety” as grounds for repressing ideas. A generation unable or disinclined to engage with ideas and interlocutors that make them uncomfortable … opens the door—accessible from both the left and the right—to various forms of authoritarianism. 🧠

If you’re feeling trapped, Windowswap lets you look at the world through other people’s windows. 🏠

The Black Creative Directory is a soon-to-launch community-sourced list of Black artists, freelancers & vendors for hire. Get Early Access. (sponsored) 📋

An awesome piece by Li Jin on how creators are unbundling work from employment and opportunities for new companies to power micro-entrepreneurship. 🔮

A new wave of consumer brands is throwing “palatable” out the window. 🎭

If you liked my previous issue on the forthcoming participatory economy, you’ll enjoy Jesse Walden’s writing on the ownership economy. As the barriers to professional connectivity have fallen dramatically, so too have the hurdles for more equitable distribution of economic value. This is a future I can get behind! 💥

The RFS100 newsletter compiles startup ideas from top investors, founders, and operators - it’s worth your time. 💡

Cool startups on my radar: Glimpse, Jemi, House of Wise, Kibbo, Moment, and Dance. 👀

If you’re wondering who’s behind this newsletter:

My name is Sari Azout. I am a design-thinker, strategist, and early stage startup investor at Level Ventures and Rokk3r. My mission is to bring more humanity and creativity to technology and business.

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