Expectations of an Entrepreneur: A Letter to Myself

At the beginning of my Bootstrap Sabbatical, all I could see was an empty horizon, a desolate landscape.

I'd written out my thesis - a blueprint of what I intended my year off to look like. But that's the thing about blueprints - they look great on paper.

Knowing what I expected of myself and what I'd committed to in public was daunting. So the first thing I did was take myself for a coffee and write down all my thoughts and feelings.

Exactly a year ago, on March 31, 2021, I penned the below letter to myself.

I read it every time I felt like I was stalling, or times got tough, or I needed a kick to get back to creating.

A year later I thought I would embrace some of that vulnerability and share it publicly.

If you're an entrepreneur, or whatever path you're currently on, maybe you'll find inspiration in it as well?

Lace up your shoes. Join me on this run.

Sydney | 31 March, 2021

Dear Kev,

You’ve just started and you’re now thinking WTF have I done?!

You tied your shoes. Chose a playlist. And now that your feet have hit the pavement, it has dawned on you, I’ve got a hell of a run ahead!

And like always, there is a doubt. And as your breath and feet struggle to find rhythm, there is hesitation and a little voice that challenges you, and says: “You know, you’re not far. You can just turn back now.”

But you never do.

You never have, and you never will.

If the journey is clear and the road is paved in your mind, you must keep on that path, because you, yourself, have set it.

And the beginning is always tough. Like your body hitting cold water, your first instinct is always to quickly resurface and take a HUGE gulp of air, just to know, “you’re safe, you’re okay!”

And that’s what this is, a journey. And no matter what happens, you can always take a breath, and remind yourself it will be okay.

And once you find reassurance, you’ll find rhythm in momentum. Soon will come that runner’s high. You’ll be so invested. You’ll be in the moment, sailing, cruising, not even remotely aware that your feet are still hitting the pavement and you’re making strides on this marathon.

And there will be barriers, blockades, road closures and probably skinned knees. Oh yes, there will be failure, probably lots of it. But this is all anticipated and expected. Don’t cry over cuts, bruises and grazes. Get on up and keep moving onto the next path and the next turn.

And you’ll learn along the way. Don’t get too obsessed with what you learned, but how you acted on those learnings and created. Because this whole year is about creating.

So may you always err on the side of action, weight the balance towards creation and continue to build.

But remember to keep focused. 

Set your goals on a project and work hard to validate it, quickly, and, ALWAYS, try sell it first. Seek forgiveness, don’t ask for permission.

Don’t hesitate to put yourself and your projects out there. That is what you said you would do, that is your own pledge and commitment.

You’ve put out a lot of goals that dictate what you’d like to see looking back a year, but it’s not always as simple as that.

As the saying goes

Mann Tracht, Un Gott Lacht

Yiddish for “Man plans, and G-d laughs”.

Don’t fear the sideswipe. Embrace it, because it is likely inevitable.

So what would I really hope to see from you in a year?

Well let’s start with anti-goals, things I would not like to see:

  1. A sense of failure – you’ve already taken the plunge, how far you swim is merely further success points.

  2. You’re incredibly stressed and unhappy – entrepreneurship is really fucking hard. You need to work hard to achieve big things, but remember that athletes spend more time resting than training and competing.

    Take breaks, meditate, do yoga, exercise – the restoration time is as important as the “go” time.

  3. You burn a LOT of bridges – life can be categorised into buckets: work, personal/health, friends, family. This year is about work. Based on the Four Burner Model it will take up a lot of gas. This means that some burners may get a little less attention. That is fine, as long as they still get some.

    Prioritize your health than your family, than your friends – you might need to lean on them more than ever to burden the load. If they don’t offer support, don’t guilt yourself into feeling like you let down the team – relationships are a two-way street.

    You are also wanting to, well you need to, connect with your own tribe for support in this journey. They will take up some gas and they are the gas you’re going to need to get through. If time is limited for friends and family, make sure it matters – depart when it does not.

  4. You’ve put yourself into another “job” – avoid spending too much time solving other people’s problems, especially if the relationship involves a monthly salary or a stipend.

    Your goal is to scale, not trade your time for money.

So what do you want to end the year with?

  1. Tangible products / businesses – whether they worked or not, it would be ideal to see a portfolio of attempts. If your first attempt was a hole-in-one – no one is going to judge the lack of multiple swings.

  2. Dollars in the bank! – the goal is high, its daunting, but without aspirations we don’t know how high we can jump. But jump, you must!

    If you put over $10,000 in the bank, from products, you can pat yourself on the back and say “Well Done!”, because anyone can exchange time for money, but only a few can create, build, sell and capture value by exchanging a solution to a customer’s problem. If you hit $50,000, you can be more than incredibly happy!

  3. You learnt and leveled up – to end, this is a reminder that whilst dollars pay the bills, this experience is a journey of growth. It’s about learning and leveling up. With that, may you feel more confident, more capable and more enabled to keep doing what you’re doing, or whatever you decide to do next.

Keep going!

Wishing you all the best, 

Kev

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31/03/2021

Thank you for taking the time to read this and join me on this journey.

If you missed the beginning, you can find out more about the Bootstrap Sabbatical here.

And my current progress here.

And, finally, if you’re interested in getting more insights that I don’t share publicly, I have a private newsletter where I share business ideas, lessons and other tools to help entrepreneurs level up. It’s free. You can sign up here.