When you’re working in a job or career that is less than optimal, it’s easy to fantasize about working for yourself. After all, you’ve already thought about how differently you’d run the company you’re working for if you were in charge.

However, the transition from employee to entrepreneur can be more challenging then you think. My most recent leap into entrepreneurial life was my third, but most meaningful. The two previous businesses I established where done while I was still an employee, but this time I truly made the leap. As a result,  I’m uniquely positioned to talk about the right way to make the leap.

Choosing entrepreneurship has been the best decision of my life. It’s afforded me the opportunity to create my own economy and make a meaningful impact on the lives of others. If that’s one of the many reasons that’s tempting you to leave your nine-to-five, consider the following four questions before you make it official.

Do You Know Why?

Not only do you need to know why you want to become an entrepreneur, your “why” must be a compelling one. Hating your boss or your job, or just wanting freedom and independence is not enough. It may be a motivator, but it won’t sustain you.

Your “why” is what will keep you committed when you doubt yourself and your decision. Your “why” will keep you focused during those initial lean and unpredictable years. Also, the “why” that will ultimately drive your success won’t be the same as what drives someone else. It’s intrinsic, a deeply personal choice that must have great meaning to you, and you alone.

So what’s your big “why”? Read Simon Sinek’s Find Your Why if you need help discovering your true motivation for taking the leap. Your life experiences often inform your life’s work, so look for the the patterns in your life to help discover your why.

Once you’ve landed on this powerful piece of information use it as the driving force behind every action you take. When you’re deciding on the type of business venture you’ll start, or setting goals for the quarter or year, and even when choosing your clients, check to make sure they’re in alignment with your big why.

Can You Be Your Own Boss?

As an entrepreneur you have an opportunity to create something impactful, but it requires hard work and perseverance. So, let me ask you a question. Just how many hours a day do you work? I don’t mean the time you’re in the office, I mean the actual time you spend working?

Employees who dislike their jobs tend to be clock-watchers, just waiting for the “workday” to end. But that’s not the entrepreneurial life. There’s a lot of hard work and initially you’ll be spending some sleepless nights working in your business. I don’t want to scare or discourage you, but it’s important to have a realistic picture.

Employees wait for direction while entrepreneurs make big decisions, take risks and get things done. As an employee you may have become used to waiting for someone else to present solutions, but as an entrepreneur if you wait for things to happen you could be out of business. You can’t simply do what needs to be done, you have to look ahead to create opportunities and foresee obstacles. What you do or don’t do in your business will become obvious in the next 60, 90 or 180 days.

Be honest and ask yourself if you’re ready to be the boss. If you’re not sure, start acting like the boss now. Create new habits and routines and start working like an entrepreneur in your current job.

Are You Ready to Change Your Mindset?

Working for yourself is unlike anything you’ll ever do. The work requires you to live continuously outside of your comfort zone.  What’s your tolerance level for disappointment and perceived failures? Are you prepared to work for days, weeks or even months before getting paid? How’s your patience level for learning new things? What’s your mindset around money? Are you good at self-promotion? Do the words sales and marketing make you uncomfortable?

The path to success is never straight, easy or immediate. More than money, time or resources, most entrepreneurial ventures fail because of a faulty mindset. It usually starts with the misnomer, “if you build it they will come”. Yes you have to build something to create a business, but what makes your tribe come running to you is their knowing, liking, and trusting you. That comes from your ability to sell, market and persevere.

One of the best ways to develop an entrepreneurial mindset is to change the way you’re thinking. There’s a direct correlation between what you think and what you do. Our thoughts about certain situation and circumstances form our beliefs and at that point it becomes hard to separate fact from fiction. Examine your thoughts (and beliefs) about money, failure, learning, and self-promotion. The proverbial “mindset safety net” you’ve enjoyed as an employee is removed once you become an entrepreneur.

Do You Have a Network of Support?

This biggest lesson I’ve learned as an entrepreneur is that you can not do this alone. As an employee you have an unofficial network of support built into your job with your co-workers and leaders. Since entrepreneurs usually work alone, you’ll need to develop your own network of support.

Networking is an important aspect of building your business. You’ll receive great insight when meeting with others who are similarly situated. Fostering relationships through these networks can also lead to client referrals and leads. Attending training events, conferences and workshops will give you the opportunity to continue to grow in your knowledge while increasing your network.

Early on as an entrepreneur, I’d recommend you find a coach, mentor or mastermind group. Surrounding yourself with a group of experts and industry veterans will save you considerable time and provide you with great resources. Through your journey as an entrepreneur you’ll find you’ll need varying levels of support and guidance, so it’s not uncommon to have several mentors and coaches along the way. Don’t make the mistake of believing one person holds all of the answers for you.

Finding a coach or mentor is a very personal one. There are numerous facets to running a business and as you master one area you may find it’s time to find a different coach or mentor to help you accomplish another. That’s ok and perfectly normal. It’s important to find someone whose been where you’re trying to go. As helpful as friends and colleagues may be, they won’t be as intimately well-versed in your business or have the experience to guide you where you need to go.


There are several other practical considerations to becoming an entrepreneur that I didn’t mention in this article. While finances, time (with regard to when is a good time to make the leap), and legalities are important, I believe the four questions outlined above, once answered, will lay the groundwork for a successful transition.

I help successful professional women who’ve climbed the ladder of success only to realize they’ve climbed the wrong one discover their life’s work. Their life’s work could be found in a new career or a new business venture. After years of toiling and struggling to build a fabulous career they’re most scared of what people will say or think if they dared to leave. But the career they’ve built is not the career they want. My work and process prepares them by giving them the tools and confidence needed to unapologetically do what they know they were always meant to do. 

Is that you? Then let’s connect and explore whether or not you’re ready to make the leap.


  • Carol Parker Walsh, JD, PhD

    Helping successful professional women courageously step into their life's work.

    Dr. Carol Parker Walsh is career & professional development consultant who helps successful professional women who've climbed the ladder of success but feel called to do something new, discover and courageously step into their true authentic calling. She's a TEDx speaker, Amazon best-selling author, an award winning consultant, and is a current member of Forbes Coaches Council. Carol can be seen regularly on ABC affiliate KATU's AM Northwest morning show and in her column in the Vancouver Business Journal. Learn more at http://carolparkerwalsh.com