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12 Wild Phases of Entrepreneurship: What's Yours and What's Next?

12 Wild Phases of Entrepreneurship: What's Yours and What's Next?

Euphoric super fans tout entrepreneurship as the best thing since the iPhone. Others describe it as a never-ending slog of busywork. The truth lies somewhere in the middle. If you’re a new entrepreneur, or an aspiring one, read on to see which phase of entrepreneurship you’re in right now, and how to prepare for what’s next.

Phase 1: I Wish

As with any 12-step program, the first step is admitting you have a problem. In this case, your problem is that you want to be an entrepreneur, but you’re not. Yet.

Many people live in the “I wish” zone for years before they make a move. Watching from the sidelines can be a good way to learn, but there’s only so much you can soak up as a spectator. When you’re ready to get in the game, do this…

Talk to people about your desire. Say it out loud. It takes the edge off. “My name is __________, and I want to start my own business”. Now you’ve put it out into the universe. It’s a small but important first step.

Phase 2: I Will

Starting a business takes more than just talk. This is where you actually do something about it. Have no idea where to start? Join the club. That’s where all entrepreneurs begin. You’re in good company.

There’s no need to up and quit your job tomorrow or sink your life savings into product development right away. Take it slow. Slow is good. Slow gives you time to plan.

Take a class. Hire a coach. Join a mastermind group. Attend a conference. Write a business plan. These are wonderful ways to invest your time and money when you’re just dipping your toe into entrepreneurial waters.

Phase 3: Plan, Plan, Plan

So, you’re committed to starting your own business. You will need to do a lot of planning. This includes a formal business plan. Do one even if you’re a simple one-man-show and you don’t need a cent of funding. Why? It will force you to consider everything, so you’re really prepared for launch. There are a ton of business planning tools out there. Find one that works for you.

A word to the wise: You may be tempted to stay in planning mode indefinitely, especially if you’re a details person. But you will never know everything there is to know. At some point you have to jump. Much of entrepreneurship involves tweaking along the way, so when you have your ducks in a row it’s time to launch.

[Related: Why You Should NOT Leave Your Job To Become An Entrepreneur]

Phase 4: Ta-da!

Jazz hands! Neon lights! Confetti! Like Rafiki holding the little lion king out for the world to see, your launch is when you introduce your baby to the world. This is an exciting step for a new entrepreneur.

When you hang up that OPEN sign, enjoy it. Be proud. You’ll be exhausted from the work it took to get there, and there are sure to be hiccups, but take a moment to pop some champagne and drink it all in.

Phase 5: Crickets

Maybe there wasn’t a line-up around the corner on launch day. Or maybe there was, but the launch rush has now subsided. You may wonder, where did everybody go? Do. Not. Panic.

The post-launch lull is when you take a deep breath and regroup. Go back to your business plan. Are you following it? Is there something you missed? What adjustments need to be made? If you did not create a business plan, for the love of Pete get some help and create one! Pronto.

Seek feedback from people who will give it to you straight - from clients, from industry veterans, from successful sophomores. Ask them to tell you what isn’t working. Gloria Steinem said, “The truth will set you free, but first it will piss you off.” Listen to the (potentially frustrating) feedback and make your adjustments.

Phase 6: Impostor Syndrome

Impostor syndrome is a psychological phenomenon associated with the fear of being discovered as stupid or unworthy. It happens to all entrepreneurs at some point.

You will occasionally (or often) feel like you are out of your league. You will feel like you don’t speak the language. Venture capital or equity funding? And what does “bootstrapping” mean, anyway? Everyone else seems to know more than you do. The learning curve for entrepreneurs is steep, and you will feel incompetent at times. This is normal. Breathe.

Aristotle said, “The more you know, the more you know you don’t know”. As you learn more about running your own business you will also identify your knowledge gaps. Notice them, and find a way to learn. Don’t compare yourself as a newbie to the guy who’s 20 years in. You will learn in due time.

Phase 7: Sponge

This is where you soak up information to fill your knowledge gaps. Note: I did not say this is where you learn everything about everything. That isn’t remotely possible, so don’t try, lest you burn yourself out or feel the urge to throw yourself off a cliff.

Decide what’s important for you to learn during this stage of your business. To avoid entrepreneur overwhelm pick one or two things to learn about. What’s one thing you can do this week to help you get there?

You will return to the sponge phase again and again as your business evolves. There will always be something new to learn. Embrace it as a part of the process.

Phase 8: Everything is Awesome!

You’re doing exactly what you dreamed of and you’re getting PAID for it! These moments are why you became an entrepreneur. You’re most likely to experience the “Everything is Awesome!” high when you first quit your job to become an entrepreneur, at launch, after an especially lucrative month of business, when you work with a dream client, or when you take a random Friday off work just because you can.

Enjoy these moments. They don’t happen all of the time, but they’re damn satisfying when they do.

Phase 9: Panic!

You may encounter entrepreneur “bag lady” fears. They go something like this: I have no idea what I’m doing and I will never make money doing this. I never should have left the security of my job. Soon I will be forced to live out of a shopping cart on the corner, and my old colleagues will point and laugh at me on their way to work.

Fine. Allow yourself to indulge in this ridiculous dystopian fantasy for exactly two minutes. Do you feel better? I didn’t think so. Feel the fear, and then do something about it. What’s one small action you can take to help your business today? Do it.

As an entrepreneur you will likely vacillate between Everything is Awesome and Panic. Try not to spend too much time here. Panic breeds paralysis. Keep moving.

[Related: What I've Learned As An Entrepreneur (And Didn't Know As A Corporate Exec)]

Phase 10: Buddy Up

By now you’ve realized that you can’t do it all by yourself. If you try you’ll burn out. It’s time to focus on your forte and outsource the other bits to strategic partners. Hire a designer, a distributor, tech support, admin support, an accountant, a social media partner. Getting stuff off your plate frees up more time and energy for you to do your best work.

Phase 11: Switcheroo

You’ve learned enough about your business to realize that you need to make some changes. Perhaps you need to refine your offering to two core services instead of ten. Or maybe you need to make a radical shift in the direction of your business.

Face-saving entrepreneurs will call this a “pivot”, which basically means, “I was doing this one thing, and now I realize I should be doing this other thing instead”. You might feel like a fool for not getting it right the first time around, but I challenge you to find any entrepreneur who got everything right from the get-go. A switcheroo of some sort happens to many entrepreneurs over time, and I like to think of it as a rite of passage.

Phase 12: Business as Usual

Business as usual for an entrepreneur means juggling a little bit of everything and, as you know, the only constant is change. There will be ups and downs and celebration and panic and LOTS of learning. And you’re ready for all of it. You’re a bonafide entrepreneur now. Welcome to the club. 

Sarah Vermunt is a career and entrepreneur coach, and the Founder of Toronto-based Careergasm. Her mission is to help people create work that feels good. Follow Sarah to feel-good work at

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