Advice I’d Give to Someone Who’s Starting

The following is an excerpt from a newsletter published March 14th, 2024


A photo of a book titled "How To Dotcom" sits on someone's front lawn.

Whether you're starting a new business or pivoting within an existing one, here's the general advice I'd give to someone who's starting.

Consider this a choose-your-own-adventure kind of newsletter.

Take what's needed. Leave the rest.

— Focus on (and measure!) what's in your control.

You can’t control how many people are going to buy your work. You can control how many times you show up and talk about it.

(And how you talk about it and perhaps how you feel when you talk about it…)

It’s wonderful to have goals and targets in your business (sales goals! visibility dreams!). It’s necessary to figure out what actions you can consistently take to achieve them.

Business culture is so wired for outcomes and shortcuts that we forget the basics of doing good work and showing up on behalf of it.

In general 💡: If you’re only measuring the results of your efforts and not the efforts themselves… you'll feel powerless to your own success/failure.

— Good enough really is good enough.

There's going to be information you want that you simply won't have.

If you're struggling with language, offer design, or pricing… It's probably because you haven't done this before!

You might not know what you have, who you are, or what you do until you start (especially if your work is closer to art).

The same goes with plans. Just as no self survives a real conversation (h/t David Whyte), no plan survives the real world.

Your budget, business model, website, event, etc., doesn't need to be exact to be effective.

Is it in the realm? Is it an educated guess?

— Make educated guesses.

There is almost certainly a middle path between Absolute Certainty!! and throwing spaghetti at the wall.

Small bets. Educated guesses.

Keep your experiments focused.

— Give things a chance to work.

Sometimes we get all the information we need from trying once (nope, not that!). But more often that not, the growth comes from staying with it.

Please, please give yourself many chances to talk about your work before deciding it’s not working. And even then, get curious as to why (the structure, the timing, the price, the place?).

So much of being in business is running experiments, and experiments need time. More time than you think.

Please! ❤️: Make marketing a practice. Give people a chance to buy from you.

— Resist the urge to optimize early.

Trying and refining are two different stages.

1) I’m trying this to see if it works.

2) OK it works! (I like doing it, people like buying it, etc.). Now it’s worth investing a bit more money, energy, and intention into making it even better i.e. more beautiful, more easeful, more elegant…

But remember 💡: “Don’t optimize what shouldn’t be done.” (h/t Kenneth E. Boulding)

— Start with capacity.

I was so nervous about starting this iteration of my business after years of being consumed by my mental health that step one was to build my capacity. Rather than have an income goal for my business (I cobbled together an income bridge from freelance work, savings, an inheritance, and my line of credit), my “goal” for the better part of a year was 10 hours of deep work a week.

Can I focus my best attention toward what matters to me for 10 hours a week?

Tip 💡: If there are any capacities that underpin your ability to do your business/project, try focusing on strengthening those first.

— Build income bridges.

Does your business need to make money right away and if so, how much?

Some people like the forced scrappiness of “leap without a net”. Some are forced into that scrappiness because of circumstances beyond their control. Some people have temporary/indefinite financial support from partners, family, savings, etc.

Regardless of your personal circumstance, savings buffers and income bridges (and our ability to create them) are our allies.

Jobs are great. Bridge work is great. Leaving a job/world/gig you hated and then going back to it part-time a few months or years later is totally normal. There is no shame in you doing what you need to support yourself financially.

There is no prize for linearity (I started my business and never had a job again!).

There *is* something meaningful in ongoing devotion.

— Be mindful who you get advice from.

For the most part, the advice someone gives tells you a lot about them and not much about you.

Most people give advice based on what would/did work for them or what they believe is possible for themselves, rather than what’s actually available to you.

It's also all too common to be given advice for resources you don't have access to, a business you're not interested in running, or a growth stage you're not actually at.

Be mindful! Practice discernment! You are the ultimate authority on you!

Related: 12 Beliefs that inform my advising approach.

— Invest proportionally

Proportionally to what, you’ll have to decide. Investing a lot of money upfront in your business *can* put stifling pressure on some folks (especially if it's work you haven't done before, a hobby/passion you've turned into a business, or an unproven business model). The awareness that you’re putting in substantially more money/energy than you're receiving back can actually lower your confidence or ability to see and celebrate the progress of what is working.

Perhaps your level of investment should be balanced out by the proof/confidence this will be returned to you. Or your willingness to deal with the risk (i.e. if you're not willing to lose your retirement savings, don't bet with it).

Risk is healthy! Risk is necessary! But risk shouldn’t ruin you.

— And finally, know what game you're playing.

A lot of business advice/culture is geared toward short-term trends and medium-term exits. Creating something popular/lucrative now or a company you can eventually sell.

If you’re in this for the long haul (i.e. “I want to do this work for the foreseeable future and/or the rest of my life”), make choices that mean you can keep playing the game.

It can be incredibly powerful to see the shiny object, feel the urgency in your body, and then anchor back into, “Nope, not for me. I'm playing a different game."

Business is a beautiful reflection of creation in general.

We will plant many seeds and they won’t all grow. That’s not a failing, that’s how creation works.

It’s messy. It’s beautiful. It’s unpredictable and yet it follows patterns.

By starting, you are showing a tremendous willingness to be in active collaboration with what you want.

What a worthwhile endeavour.

I'm proud of you,

— Kate


P.S. Let me leave you with that full Kenneth E. Boulding quote… “Don’t go to great trouble to optimize something that never should be done at all. Aim to enhance total systems properties, such as creativity, stability, diversity, resilience, and sustainability—whether they are easily measured or not.”  

Beautiful, yes?


Kate Smalley

Kate Smalley is a small business advisor, facilitator, and educator based in Toronto, Canada. She writes about growth and business development for principled, industry-shaping entrepreneurs.

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