Before You Quit: 30 Things to Consider Before Taking the Leap From Employee to Entrepreneur

Posted on Posted in Entrepreneurship

One of the most common questions that I get asked is: “I’m ready to quit my job, what should I be doing now to prepare to take the leap from employee to entrepreneur?” My canned response is always: “There’s no one blueprint for success, however, there are a few things you can do to prepare for the transition. So here you go:

Get Your Mind Right

While many people focus on the tips and tools to succeed as an entrepreneur, here’s what I need you to understand—your mindset is the foundation of your successFeeling uncertain about the process, working long hours without a dollar attached to your hard work and anticipating failure are just a few of the outcomes you’ll need to embrace to be successful as an entrepreneur. Here are a few other mindsets that I live by:

  • The secret of your success is found in your daily routine – What time can you allocate each day to make your goal happen? Oh and it’s not about having the time—it’s about making the time.
  • Your path will look different than everyone else’s path – Remember, “just because you took longer, doesn’t mean you failed.” So don’t get caught up comparing your journey to others. Minimize distractions by taking a social media detox.
  • Audit yourself and YOUR circle: Is this really your vision or someone else’s dream? What are you feeding your mind daily? Would you intentionally eat disgusting food? No, I didn’t think so. The same rule applies to your mind and your friendships: Nourish your mind daily with positivity.
  • Embrace mistakes and uncertainty as a part of the process—because these experiences are shaping you into who you need to be and where you need to go. My motto: Failure is feedback for the come-up. “Trust and Grow” through the process.
  • Surround yourself with Badassery – In the real world most people describe this as a network–your personal board of advisors or mentors. But since I’m all for creating your own reality, I use the term  “a network of badassery,” my personal group of rule breakers, risk takers, super connectors and champions, who actively turn their ideas into action.  Our relationships are mutually beneficial. They tell me what I need to hear, not what I want to hear. And they have an “influential voice” within my industry and advocate for me when I’m not around.

Lastly, if you’re ready to make the switch in the next 6-12 months, now’s the time to have a candid conversation with a few entrepreneurs about what it really takes to build a profitable business.

  • Make connections with at least 3-4 entrepreneurs and industry insiders. Ask your friends to introduce you to people they know who have successfully operated a business for at least 3-5 years. Invite them to coffee or a quick chat on the phone.
  • Attend a few industry related conferences to learn about the entrepreneurial process, trends, etc.
  • Listen to podcasts focused on entrepreneurship. I love Tim Ferris’s 4-hour work week, Side Hustle Pro, Hashtags & Stilettos, and The Daily Vee, by Gary Vaynerchuk.
  • Test your business idea while working full time. Can you commit to a daily after work schedule?

Prepare Your Family and Friends

I’m not saying you need the approval or permission from your family and friends to start a business. But the sacrifice that comes with entrepreneurship takes a toll on everyone around you.

  • What sacrifices will you have to make as a family?
  • How does your family feel about your decision to pursue entrepreneurship?
  • How will you balance a business and family?
  • Is your spouse willing to take on more financial obligations or household duties?

Assess Your Financial Health

  • What is the least amount of money you can live on per month? How much money do you need to save each month to cover 6 months of living expenses?
  • What does it cost to operate your business for 90 days? Consider advertising, software, inventory, credit card fees, contractors, etc.
  • How much money can you set aside in case clients don’t pay on time or business slows down?
  • Can you make any drastic lifestyle changes? Do you really need the car payment, mortgage, etc.? Can you downsize your home or take on a roommate?
  • What marketable skills can you use to make money on the side, (e.g., sell used items, sell writing or accounting services, fix things, teach computer skills, etc.)?
  • Consider opening a “Freedom Savings Account,” which can include funds for living expenses and money to cover you during slow months in business. Also if you need help becoming financially free? I’m obsessed with My Fab Finance, The Budgetnista and Careful Cents. These women are rock stars at providing a number of resources on how to become financially fit.

Take Advantage of Employee Benefits and Freebies

Many companies offer their employees professional development courses and conferences. So before you quit,

  • Take courses such as marketing, management and finance and accounting.
  • Schedule doctors appointments and routine medical exams.
  • Find out about any fees or penalties for your retirement investments and 401k plans.

Trips for Transitioning from employee to entrepreneur

Create a Business Plan

Many people say business plans are a waste of time. But I believe you can’t sit around hoping for success, you have to plan for it. When you put pen to paper & sprinkle in some action—things get real. A business plan doesn’t need to be complicated. But it should have a basic summary, strategy and implementation plan.

  • What problem does your business solve? Who do you solve it for?
  • What’s the ‘Why” behind your business?
  • Do you have a viable business idea?
  • Do you have a pricing strategy?
  • Who are your competitors? What sets you apart?
  • What will it take to make a profit?
  • What are the applications /systems and tools required to deliver your products or services?
  • How will you withstand the ups and downs of the business world?

Build the Foundation For Your Business

  • Build a website (I recommend WordPress or Squarespace).
  • Establish a social media presence. You don’t have to be active on a gazillion social networks. Pick 2-3, be consistent and master it!
  • Set up a designated workspace (especially if you’re creating an at-home business).

Related: 12 Ways to Make Yourself More Marketable

Implement Processes and Systems for Success

While running the day-to-day operations of a business, many entrepreneurs fail to pay attention to the functions necessary to take the business to the next level such as marketing, technology and customer service. What’s your plan for working on (not in) the business?

Tips for Transitioning from Employee to Entrepreneur

  • Identify systems, processes and tools to run your business. Consider the following applications:
    • Mail Chimp, Aweber, or Convert Kit for email marketing.
    • HootSuite, Coschedule or Buffer for social media marketing.
    • Intuit, Wave or Paypal for payroll/customer/ client payment.
    • Google Drive or Dropbox for storing, saving and sharing documents with employees and clients/customers.
    • Asana project management system to collaborate with teams and track progress.
  • Do you need to outsource some task? Just because you can do it all, doesn’t mean you should.

I’m happy to answer any questions you may have about making the leap from employee to entrepreneur. Shoot me an email at

Related Post