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It Won’t Be Easy - How to Prepare for Entrepreneurship

Let me start by telling you one fundamental truth about entrepreneurship:

fashion entrepreneur kristen anderson

There is no "right" way to do it.

It's like you're a pilot, flying in a plane while you're still building it…and you don't know how all the pieces of the plane go together, what they do, or how they work. In fact, you've actually never even flown in a plane; hell, you're not even a pilot. 🪂

Your plans will never go entirely as planned, expectations will be turned upside down and inside out, and without a doubt -- change will happen. So be prepared to face that reality.

If entrepreneurship was a clear, cut-and-dry path, it'd be a totally different thing altogether. It's not like grade school or college, where the point is to reach graduation and finish. The word's origin is literally 'to undertake,' which is basically the same as 'beginning a journey' or 'attempting a task.'

The path of an entrepreneur has no proper plan, and that finish line you're chasing? It's ever-elusive. There are millions of little ends, but the journey is sort of the point.

Kristen Anderson and Nicole Beals hugging on a city sidewalk in NYC
Me sharing a moment with one of my most inspiring friends, Nicole Beals, COO + Co-Founder @ TechMate!

You will make millions of mistakes, but that's no biggie. Mistakes aren't the worst thing. No, the worst that can happen is paralyzation. To be frozen and unable to act is the worst. But freezing up is just a symptom of a more significant issue, usually a lack of clarity.

So, how do you prepare for entrepreneurship? I suggest you start by writing a letter to your future self. This letter should credit you for what you're working on, where you're going, and what you'd like to achieve. It should also be a testament to what you want from your life and what is *not* going to stop you from making the changes you need to make your dreams a reality.

I like framing this exercise as a letter to your future self.

If you know me well, you know I do many things for my future self. So I always like the way of framing it around her. I don't want to make life harder for her, only better.

This is private and can be a journal entry for your eyes only. Still, I've shared some of my intimate thoughts below to enlighten you on how you can go about it.

Dear Future Self,

Sometimes your path will feel more complicated than you can even imagine right now.

The days will turn into weeks and eventually months into years. You will grind endlessly and halt on a dime for the whim and will of your customer, your factories, and your other partnerships. The wavering comes with the way of the land. It's just what entrepreneurship is. But you already know that, so don't pretend this is news to you now.

It's going to be super hard sometimes. You will undoubtedly think about quitting more often than you'd like. But, never quit on a bad day. Bad days come and go, but quitting is relinquishing your dream. Perseverance and persistence are the name of the game.

Sometimes you'll feel on top of the world, and other days may come crashing down on you in endless waves that ripple across your world.

You will wonder if you have it in you. Don't worry, you do.

The world wouldn't have brought the conditions together to get you just far enough to see it within reach but kept you an arm's distance away.

Sometimes, you'll doubt yourself over and over only to find that your gut instinct was right after all. It's annoying as all hell, but it's a kind reminder to listen to yourself better every time it happens.

Starting a business is not for the weak at heart. It's a daily grind, and it'll take a lot more out of you than you could ever imagine.

It's also the most rewarding work you might ever do.

Creating something special in the market that is your own little corner of wonder is pure magic when it works the way you want it to.

The world doesn't always work like that, though, so below are some reminders for you when times get tough...which they will.

  1. Surround yourself with people that inspire you to do better. Remind yourself often that you're the culmination of the 5 people you spend the most time with. Choose these people carefully. Evaluate them often.

  2. Read as many books as you can get your hands on, starting with our list, Top 9 Books for the Early-Stage Entrepreneur.

  3. Postmortem everything. Reflection on past failures and mistakes is critical to not repeating them. Don't expect everyone to learn the lesson the first time without this debrief.

  4. Don't be too precious with your first few ideas or iterations. Things will change more than you expect them to, and the longer you hold onto those initial ideas, the more you hinder and slow your future progress.

  5. Do more than you think about doing. Clarity comes from action, not thought. Consider the consequences, but don't dawdle, and don't hesitate.

  6. Move a little faster than what feels comfortable because we're all naturally slow to change.

  7. Try again if you face plant. It's normal to botch things up the first few goes.

  8. Test + repeat, iterate.

Remember, you're a badass dreamer and entrepreneur! You've got this.


Your Future Self

This is just an example of my love letter to myself. Now I urge you to write one to yourself. It doesn't have to be anything like mine. Just write something from the heart that will resonate with you on those tough days. They will come. There's no doubt there, but you're mentally tough enough to handle them. So tuck this away and read it as often as needed.


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