How To Quit Your Day Job and Start Your Own Thing

catherine-mcmahon-10118-unsplashSo many of you are interested in how on earth to stop doing the job you hate and create an entrepreneurial life where you are the boss of yourself, where you’re creating a career that will sustain you financially, and one in which you loooooove your work. I’ve taught a class for several years called Quit Your Day Job and in that class I’ve noticed over and over so many similarities about the fears of becoming an entrepreneur. I want to help you work through some of them and see not only if the entrepreneurial life is for you, but to also help you save tons of wasted time reinventing the wheel and having difficult fits and starts, when you could really be moving ahead to making your career dream a reality much faster and with less stress and anxiety.

And also instead of big mistakes and fails, little mistakes and fails! Ha! Kidding. Sort of. You’ll definitely make mistakes and have some things that don’t work, but for most people this is where they stop. They quit. They then go back to the job or life they hate and that’s not only a shame but it’s really not necessary.

And what’s even worse? The world then does not benefit from your creation! And far as I see it, that’s your job spiritually on the planet. To get your gifts out there so other people can benefit from them.

So let’s start here:

Why are you wanting to create this entrepreneurial career? What is the gift you’re giving to the planet?

Let me start off by saying – and those of you who know me, know I’m a broken record about this –  if you’re doing it solely in the hope of making a ton of money, then you’re going to be on the wrong track. Not only will you not have the juice long-term, but you also won’t have the energy and enthusiasm to sell whatever you’re creating, nor will you be able to keep your employees engaged. In short, it will be a shit show.

But that doesn’t mean you can’t make money. Quite the opposite in fact! People who are passionate about their work are the ones who sustain energy over the long-term. They are the ones the ones who wake up at 5am with a killer idea and bounce over to their laptop or notepad or studio and start working on it.

And cool is that? You got up at 5am BECAUSE YOU WANTED TO!!! Whaaahhh??

What I’m so amazed at is the diversity of ideas in my students. One is creating adorable crafts with her hands to sell online. One is a coach but wants to specifically start to work with women over 60 who want to move into consulting so as not to be tied down so they can travel.  One is an actress who wants to create original shows for kids about tough issues. All of these students came to me desperate to do their project and terrified it wouldn’t work or sell and they’d have to give it up.

Now. There are a billion ways to be an entrepreneur. You CAN keep a day job, or even preferably a job you actually like, while you do your creative work on the side. You can quit everything and wing it. Or you can do a slow shift. It depends of course on your financial situation and your bravery, and your support system, your entrepreneurial habits, your marketing knowledge, and of course, your creative skills.

Next year we will be offering a digital course on this you that can download and do in your own time. If you want to be notified of that, just get on our mailing list by going to But for now, I’ve been an entrepreneur for 30 years and have been giddy with enthusiasm most of the time (with some minor hair-pulling days), and have made a very good living at it, so let me help outline a few things to get you rolling.

First, let’s talk about your mission. Write these down if you can:

  1. What gifts do you have?
  2. What gives you joy?
  3. Who do you want to help?

If you put all three of these together, you’re going to have a good shot at a successful creative entrepreneurial career.

So let’s actually start with your idea that you have. What gives you joy about it? So say you love creative writing and you want to create a workshop for writers. First question… does it give you joy? (I’m sounding like Marie Kondo here!) Does it spark joy when you help other people get good at writing? Or…. do you simply like writing yourself? Because those are very different things. You can love writing but not love helping writers. And that’s completely fine. You should become a writer not a teacher.

But if you love teaching someone and watching them get all juiced up by your workshop, and you could see yourself waking up at 5 in the morning with a great new exercise for teaching writing, then you’ve got a hit on your hands!

Here’s another question: What about the delivery of it? So for example, if you used to like teaching or leading your workshops, but now you are dragging your ass to class, can you suss out what the problem is? Is it the students? Is it a group that’s not engaged? Is it just you’ve been doing the same thing for too long and it’s gone stale? Is it that you don’t like the subject? Is it that you don’t like the company or community you’re working with? Do you feel repressed by what they want you to teach?

See if you can figure out just what it is and write it down.

As we go forward and you’re making changes in your work life, if you don’t know intellectually what was wrong last time, you won’t see the warning signs of the next iteration of your career. It’s like, you know when someone has a break up and they get into a new relationship quickly and it’s exactly the same problems as the last one? Yeah, you don’t want that. I teach a process called Get Lost (you can listen to my podcast episode on getting lost by clicking here.)

If you allow yourself to be lost for a bit, answer the questions that I just went over. Then, you can actively and consciously find something new that ticks all your boxes for what you want.

Speaking of ticking boxes, if you don’t have my downloadable Life Satisfaction Checklist Worksheet, go to and get one for free. That will also really help you with this.

Okay so let’s say you want to teach a workshop on writing. You love teaching and you love your ideas and you are getting up at 5am bouncing out of bed. (Or ya know, not necessarily 5am… But at least you wake up excited some days with ideas.)

So the next question is: what exactly about your idea for your creative entrepreneurial career gives you joy? And now the next question is:

Why do you want to do this? The only reason we do things or plan to do something in the future is because of what our imagination tells us we will FEEL in the future when we do or have them.    

So what are you picturing? Autonomy? Energy? Excitement? Fun? Newness and learning? A steady or growing income? Connection? Delight?

So for those of you who have worked with me before know that I stress how important it is for your feelings to match your plan. In other words, if say, you wanted to build a creative entrepreneurial career in which you started an old school hippy restaurant but the things on your list that you want to feel are: security, calm, peace, connection, newness…. Well this might be a terrible choice.

Restaurants are notoriously insecure financially, and even though you love the hippy vibe, a restaurant with a lot of needy hippies might be the opposite of peace and calm. ☺ You may feel actually totally disconnected as people come and go without getting to know them (both the customers and the employees which have a high turnover rate), and while you’ll scratch the itch of needing newness while you build it, that will turn to tedium if you have a low tolerance for consistency after the thing is up and running.

Gah! What’s a creative entrepreneur to do???

We are strategically looking at these questions, right now, before you start. So again, write down the feelings that are most important to you to have in life. Then figure out which of those feelings you get at home, with friends, etc and which of those feelings you want or need to get from your work.

Next! Research! Really dive in and meet people doing something like what you want to create. Ask them what a typical day is like. Ask them what THEY feel. But don’t just ask one, ask several. Research research research. This will save you GOBS of time where you could end up running down the wrong rabbit hole hoping to get what you want only to end up with something you don’t.

Okay to reiterate: #1 – Write down a list of the things you want to feel in your life and each day. Write them ALL down. Then pick the ones that are most important to you, that you cannot be happy without.

#2 – Research your hoped-for entrepreneurial life. Ask questions of others and of yourself. If you want to do graphic design, are you someone who can work alone all day on your computer without getting lonely? Are you someone who can take direction from someone else even if you don’t like their idea? Things like that. Real tangible questions that help you see what you imagine the work will be link versus what it might really be.

And #3 –  look at these two lists and ask if they match up or at least match up enough. Can you get some of the things you need to be happy – like connection – outside of work enough so that during your work day you don’t mind being solitary? Or is that really important and you need to figure out where you could work as a graphic designer that is in a room full of people?

And finally, back to where we started: make sure the work you pick is not just because you have dollar signs in your eyes. YOU WILL NOT BE ABLE TO SUSTAIN THAT. You will lose energy and enthusiasm and connection to yourself if it is entirely about money. And you won’t really be able to sell yourself and your work unless you truly love the work itself. You won’t be able to get or keep excited employees and trouble because it does seem like it should be that simple.

But starting at the beginning of either a career shift or building one from scratch: If your ideas for marketing also won’t probably work. If you want to create the next Rubik’s cube, you’ve gotta be someone who adores game design. That is the first question. Do I love this thing I’m thinking of making? Do I love the product this career is built upon?

Just a little side note: Remember the saying Do What You Love & The Money Will Follow? Ugh. Bad news: It’s not that simple at all. And a lot of entrepreneurs get into you figure out what you want to FEEL when you have this career of your dreams, then all the failures and mistakes and difficulties will be easier to handle because you’ll know where you’re headed  — not in terms of what the end product will look like. If you’ve listened to me at all you know that improvising a great life means you basically have no idea where things are headed! ☺

But here’s the deal! It won’t matter exactly where you end up. You’ll end up somewhere where you are happy and confident, and engaged and enthusiastic. And that will work if you do these steps.

If you want to hear more about these really fun programs of self-discovery , like my upcoming Improvisation For The Spirit workshops and retreats, or my Workshop Teacher Certification Program, just go to


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