What Business Should I Start?

artists creative entrepreneurship entrepreneurship how to Feb 15, 2023

How do I decide what business to start?

Here are some questions you may not have considered yet that can help you make the best choice for you.


First, I want to say that most of the people I work with are incredibly talented in a lot of different areas. They have a wide variety of skills that could all be monetized. Maybe they’ve freelanced, or spent years cultivating a variety of special interests.

This is awesome — AND it can make it challenging to determine which of these things they want to turn into a business.


A lot of advice will tell you to pick the thing that will be the most financially lucrative; or maybe to go with the area you have the most existing professional connections. The thing that “makes the most sense”. But for me, these concerns factor lower than you might guess.


The question I might ask is… What do you want your days to feel like?

What makes you feel rich and successful, regardless of how much money you have?


The things that make me feel rich and successful have nothing to do with how much is in my bank account really.
Before I started building this business, I thought carefully about what I wanted my life to feel like.
I wrote out my ideal day from beginning to end.
I thought about how different my ideal day was from my day-to-day life at the time, and what I'd have to change to get to my ideal day.

Then I designed my business around that.

For those of us who want to work for ourselves, a big part of the appeal is knowing what we want our life to feel like, and knowing we're not going to get that working for other people.

Unfortunately, the idea that money comes from hard work, and the pressure to defer what we want thinking that we have to "earn" it first, can cause us to replicate exactly the overworking and under-earning structure we're trying to get out of in our new businesses.


The fear that if we don't accept clients at any price we'll end up with no money.

The fear that if we say no to working early mornings or late nights or weekends we'll end up with no money.

The fear that if we do what we really want to do vs the thing that sounds like the "safer" choice, we'll end up with no money.

The fear, the fear, the fear.

We may find ourselves saying yes to everything, overextending ourselves, working way too much for way too little, and thinking that somehow, someday, we'll finally "earn enough" to cut back our hours or raise our prices....but someday never seems to come.

I knew there were some things I wanted in my life, that felt like wealth to me.

Here are things in my life that make me feel rich:

Slow mornings.

It's storming in California and I've been thinking about the decades I spent commuting to work in all weather, early in the morning and late at night, usually on busses and trains, carrying a days worth of food and water and changes of clothes and shoes in duffel bags.

One thing I knew was that my ideal day included a long slow morning with no commute (so I had to structure a business where I don't work before 11am most days).

Fridays off.

I love Fridays, and I love dedicating them to pleasure in honor of my planetary ruler, Venus.I decided in my ideal week I wanted the freedom and flexibility to give myself every Friday off.

Being able to work from anywhere.

After years of teaching in-person classes or working on-site, where I could never leave town because I had to be somewhere, I wanted to be able to work from anywhere.

I knew my ideal business gave me the freedom to work from a hotel, an airbnb, a cafe, or my bed if I wanted to. Or if something came up and I needed to go be with family, I could do that at a moment's notice and not have to worry about getting "permission" to be away.

These were part of my ideal day/week, and they felt like extreme luxury to me (they still do). They're not dependent upon how much cash I have on hand at any given time, but they feel opulent in my body.

And I didn't have to wait until someone gave it to me, I didn't wait until I hit a financial milestone to do them, I didn't have to retire to get them.

At my business I'm the boss, and I don't have to ask anyone for permission, so I built my schedule to include these things from the very beginning.

This allowed me to experience my ideal schedule damn-near immediately, and the joy of that feeling was able to seep into every other choice I made about my business.

There's a whole different direction I could take this, about how all of this is work on boundaries, standards, and raising minimum requirements, but that's a different sermon for a different day.


Today I want to point out that knowing what I wanted my life to feel like helped me clarify which of my (many ­čĺů) marketable talents I wanted to build a business around.

There are a lot of things I could do, but not all of them would give me the freedom and flexibility I was craving at this time in my life.


This is just one of the criteria I use when I help clients decide which of thier many skills and talents they want to leverage into a business, or settling on which strategy is right for them.

If you want to be able to work from anywhere, we shouldn't open you a brick and mortar store!

If you want a lot of time to work on your art or be with your family, we shouldn't build your whole business on 1:1 work.


I'm sure you could do a lot of different things, but just because you can doesn't mean that's the choice that will make you happiest. And I personally believe there's no criteria more important to put at the forefront of your decision making process than that you enjoy your days. (Now, not someday.)


Here's some journal prompts to explore to help you decide what business to start:

  1. What's your ideal day/week like?
  2. How is that different from your days now?
  3. What would make you feel rich in your day to day life, that doesn't have anything to do with the number on your account balance?
  4. What type of business would allow you to have these types of days now (or as close to it as possible)?


If you know you want to start your own business, but you’re not exactly sure what business you want to start, I urge you to consider these questions. Build a business that supports the type of life you want to live while you’re building it, not someday in the future.




Want help? I’d love to assist you in building your dream business.

There are 2 ways to work with me: in my hybrid coaching/membership The Elemental Entrepreneurship Coven, or in 1:1 Coaching.

To join The Coven: Click Here.

To review 1:1 Coaching packages: Click Here.


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