Seven Things to Consider Before Ditching Your Corporate Gig

By: Debra Boulanger

Have you ever wondered if you’re entrepreneur material? You’re sitting at your desk, bored to tears or stressed to the max. Maybe you’re not getting the acknowledgement you want and deserve, or the options for moving up just aren’t there.

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. Women are starting new businesses at 1.5 times the rate of men.

The aging workforce is also fueling this rush to entrepreneurship. No longer just for 20- and 30-somethings, women in their 50s and 60s are starting new ventures by turning their passions into profitable businesses. It takes a certain type of woman to leave the safety net of her corporate gig and take the risk of starting a business.

In these last six years with The Great Do-Over, I have seen it all — women entrepreneurs succeeding, launching, and growing a business beyond seven figures, and others who floundered and eventually bootstrapped themselves back into a job.

Before you go packing up your desk, 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 are born out of a passion to solve a problem. What is your big why? What problem do you see in the world? What problem have you overcome in your own life? The best business concepts solve a specific problem for a specific ideal customer.

[Related: Confessions of a Purpose-Driven Company: What I Learned When I Tried to Save the World]

Can you tolerate risk and uncertainty?

Brush up on your yoga practice — the entrepreneurial journey is not for those that can’t handle stress. 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 your research and market-testing up front, and make the leap only when you have a proven concept and path to success.

Is there a clear path to money?

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 you need to close? What is the average value of a sale? What actions must you take now to ensure you meet your month/year-end goals?

[Related: Taking Control: Managing Your Business Finances]

Can you implement and get things done? Are you a good delegator?

Ideas are easy. Getting sh*t done is hard. It’s impossible for you to take on all the tasks needed to start your business. You need a team.

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 running the blog and managing your e-mail campaign. Make sure you are focused on the most critical tasks — those 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 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? Fear comes in many shapes, sizes, and 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?” 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, 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, 50, or 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?

[Related: Why You Should Put Your Fears Aside and Act on Your Own Business Ideas]

Debra Boulanger is a launch expert. She provides deep insights to her clients regarding how to launch and grow a successful venture that meets their lifestyle and financial goals.

Originally published at



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