Have you ever wondered, “Am I entrepreneur material?”

Here you are… sitting at your desk, bored to tears or stressed to the max. “Is this where I want to be? Is this it for me?” you think to yourself. “Do I have what it takes to go out on my own?”

As women over fifty, that’s the $64,000 question.

The momentum of women leaving corporate careers to start their own ventures has increased 68% over the last five years. There are nine million women owned businesses in the US and roughly eight million are solopreneurs with average revenues of only $56,000. In fact, women are starting new businesses at 1.5 times the rate of men.

BUT only 2-3% of women owned businesses will reach $1M in revenues. It’s not that $1M is the holy grail, but if you are building a substantive and sustainable business, it is a critical milestone. It’s equally acceptable and rewarding to build a lifestyle business doing something that you love and that enables you to have the freedom and flexibility you crave to live the lifestyle that suits you now.

The aging workforce is also fueling this rush to entrepreneurship. No longer just for 20 and 30 somethings, women not yet ready to retire in their 50’s and 60’s are starting new ventures by turning their passions into what they hope will be a profitable business.

Yet for all the momentum in this trend to entrepreneurship, there are an equal number of women miserable in jobs they no longer enjoy for fear of not getting another, and not believing they can generate enough wealth out on their own. It takes a certain type of woman to leave the safety net of her corporate gig (even if it’s not fun anymore) and take the risk of starting a business.

This is my sixth year after leaving my high-paying corporate job to start The Great Do-Over. I just let out a deep breath and wiped my brow… happy to have passed that critical five year mark where most businesses go belly up.

In these last six years I have seen it all – women entrepreneurs succeeding and launching and growing a business beyond seven figures and others who floundered miserably and who eventually bootstrapped themselves back into a job.

I’ve woken up in a cold sweat in the middle of the night wondering how I would pay the bills. I’ve gone down dead end roads. I’ve learned about grit, insight, intuition and the importance of steady implementation.

People say I’m extremely disciplined – I’m not sure. I know I am wedded to my BIG Why of helping you succeed in launching a business and I have decades of experience behind me. Plus… I’ve learned to dance with fear, and can teach you how too…

So before you go packing up your desk and hanging out a shingle, it’s a good idea to ask, “Am I entrepreneur material?”

Here’s a quick checklist to see if heading out on your own is right for you.

Do you have a big WHY? The most successful companies were born out of a passion to solve a problem. Joe Gebbia, co-founder of AirBnB, beyond an initial need to make their rent, seeing a need for hosting people for a conference when the hotels were full, rented out air mattresses in their living room. “Air Bed and Breakfast” was born! They wanted to create an entire experience for people from the very beginning and shared their city with people who arrived as strangers and left as friends.

The idea was born. “I bet there are other people in the world who would like to share their homes.”

“AirBnB was created based on a problem we solved for ourselves.” Joe Gebbia, co-founder AirBnB

What is your big WHY? What problem do you see in the world, or problem that you have overcome in your own life? The best business concepts solve a specific problem for a specific ideal customer.

Can you tolerate risk and uncertainty? Brush up on your yoga practice, the entrepreneurial journey is not for those that can’t handle stress. First, you need to be a risk taker. There are no guarantees of success and there is a good dose of uncertainty on this path. Are you comfortable being uncomfortable? That’s a key question to ask.

To mitigate perceived risk, it’s a great idea to start a Passion Project on the side. Do you your research and market testing up front and then make the leap only when you have a proven concept and a path to success.

“I launched the blog out of my apartment for $700 from 4am – 8am before I went to work.” Emily Weiss, Founder & CEO of Glossier

Is there a clear path to the money? Business cases are rarely worth the paper they are written on. The plain hard truth is – where is the cash flow? How soon until break-even given the most conservative scenarios. Start with the end in mind. How much do you want/need to earn? Where is that revenue coming from? What will it cost you to get it? What needs to happen in order to get the money?

Expect to invest some of your own cash in your startup. Whether or not you seek outside capital, you will bootstrap until you get a viable product or service launched. If you are seeking outside investors, be clear on your strategy and your offer and get advice on business structure, compliance, and the best investor strategy for you.

You don’t have to give up control or sell your soul, be as smart about choosing investors as you would your most trusted employee.

Do you have a head for strategy? My motto is mindset + mechanics + metrics = money. As a new CEO, you need to spend time working ON your business as well as IN your business. How will you reach your market? What is your launch strategy? How will you gather and cultivate leads? What is your average conversion. What are your customers craving? This requires data. If you are selling a service, what is the average cost of a sale? How many prospects do I need to close? What is the average value of a sale? Therefore, what actions must I take now to ensure I meet my month/year-end goals?

“Focus on the outcome, not the activity.” Tony Robbins

Can you implement and get things done? Are you a good delegator? Ideas are easy. Getting sh!t done is hard. It’s impossible and wrong for you to take on all the tasks needed to start your business. You need a team – even if that team is a virtual assistant, a designer, and technology manager. You are the most important asset to your business.

Prioritize your time carefully and delegate well. You can’t be going after new customers, if you are posting the blog and managing your email campaign. Make sure you are focused on the most critical tasks and those are the ones that generate revenue and keep existing customers delighted.

Do you have courage to ask for what you want? This is the achilles heel of most women entrepreneurs. Men have no problem asking for what they want. They ask for money with confidence.They get people onboard to marshall their cause with bar talk over a dirty martini.

Women often don’t get what they want and deserve because they don’t ask for it. They don’t ask for the raise. They don’t ask for help. When it comes to launching their own business, they don’t ask for money. Women are used to settling for less and caring for others and they lack the much needed skill of negotiation. More women than men bootstrap themselves right out of a business. You won’t get funded if you never ask for money.

Is your why stronger than your fear? Is your belief in your purpose so strong that you are willing to learn to dance with fear to get it? Trust me, fear comes in many shapes and sizes and in many little voices in your head. It’s sticky and slippery. Just when you think you’ve got it nailed, it shows up somewhere else. Managing your mindset is your number one priority on this journey. If you are in it to win it, ask yourself, “what within me needs to change.”

When I resist the temptation to go back to bed and pull the covers over my head because I opened my launch and no-one clicked the buy button, I ask why and come up with new strategies to keep the campaign running and continually engage prospects until the program is full. Mastering fear is your greatest weapon. Cultivate it daily.

Entrepreneurship can be a lonely road. Make sure you have a mentor you can trust who will show you the ropes and oversee your strategy and fill in your gaps. Cultivate a board of advisors that shares your vision and has your back. Get tight with your entrepreneurial sisters and lean on them for moral support and guidance.

You can reinvent your career after 40, after 50, even after 60. If you are feeling the internal pull, ask yourself, “What am I waiting for?” If the corporate waters are already unsettled – who do you want to make the first move?

“I’ve come to believe that each of us has a personal calling that’s as unique as a fingerprint – and that the best way to succeed is to discover what you love and then find a way to offer it to others in the form of service, working hard, and also allowing the energy of the universe to lead you.”
– Oprah Winfrey


Deb Boulanger is a business mentor, lifestyle coach and retreat leader for smart and accomplished women who want to live a successful and joy-filled life. Find out more here: The Great Do-Over

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