letter to a friend who is thinking of starting something new

if you are thinking of leaving your job to start a company or passion project, this letter is for you too

Happy Sunday, friends. In 2020, I wrote a letter to a friend who was thinking about leaving her job to pursue her passion. If you’re a founder/artist/creator/entrepreneur, this letter is for you too. 🙏🏽

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Dear friend,

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.

Sari

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