The Road Between Employment and Entrepreneurship: How Do I Handle the Inevitable Challenges?

In making the decision to walk the road between employment and entrepreneurship, it's important to approach things with a clear and open perspective.
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I was recently talking to a newly minted entrepreneur. He was listing the things that scared him and admitted that one of his biggest fears is that he will be tripped up by the things he's not good at. Some things come easy to him, and others (e.g., admin and marketing)... not so much. So a huge question mark was whether he would be successful in business knowing that he would be challenged in particular ways.

The fear in his voice was palpable, and I could feel the juicy internal conflict that comes with being at a crossroads. Should he move forward knowing that he would be walking straight into situations that would challenge him? Or should he stay put? I empathized with him because I remember being in the same situation. I could pinpoint specific areas where I would be challenged, and was unsure whether these challenges would cause me to fail miserably.

In making the decision to walk the road between employment and entrepreneurship, it's important to approach things with a clear and open perspective. If you find yourself shutting down around the areas where you know you'll be challenged, I encourage you to think through the questions below. They can help you remain open so that you arrive at the best decision for you.

Are you willing to work through your challenges?

"The brick walls are there for a reason. The brick walls are not there to keep us out. The brick walls are there to give us a chance to show how badly we want something. Because the brick walls are there to stop the people who don't want it badly enough." ~ Randy Pausch from The Last Lecture

My first business coach told me that entrepreneurship is a deep dive into personal development, and I've experienced the truth of her words many times. Facing challenges in business is inevitable, and it's what you do with these challenges that determine how successful you'll be. It's easy to view difficulties as roadblocks that keep you from getting what you want. A better perspective is to view them as opportunities. A few questions that can give you some perspective when you're in a challenging situation:

  • How have I created the situation that I'm currently in?

  • Moving forward, what can I do to keep this from happening again?
  • How can this challenge work for me? (Instead of asking "Why is this happening to me?")
  • Are you willing to ask for help?

    "There is no quick and easy solution except to start reaching out. As you work, look for answers wherever you can. Continually build your network: your team members, business acquaintances, online forums..." ~ Richard Branson

    As an entrepreneur you are going to be challenged in many different ways. You will think you've worked through all of your kinks and have fallen into a rhythm, only to have something come at you out of left field. You'll constantly have to think on your feet and adapt as you find yourself in new situations.

    You'll be doing yourself an incredible disservice if you try to go at it alone.

    From the outset, you should work on cultivating relationships with individuals who can provide well-crafted advice. This will be your secret weapon that will help you manage even the stickiest of situations.

    In finding individuals to whom you can go to for counsel, consider the following questions:

    • How can this individual best advise me? What is his or her expertise?

  • Am I willing and able to be vulnerable in front of this person and share the intimate details of what I am going through?
  • Do I respect this person enough to follow his or her advice?
  • Are you also focusing on the benefits of entrepreneurship?

    "[F]or the past 33 years, I have looked in the mirror every morning and asked myself: 'If today were the last day of my life, would I want to do what I am about to do today?' And whenever the answer has been "No" for too many days in a row, I know I need to change something." ~ Steve Jobs

    It's easy to become so focused on the challenges that you forget why you considered becoming an entrepreneur in the first place. What got you thinking about leaving employment to become an entrepreneur? How would starting your own business allow you to experience life the way you want to be living it?

    Focusing on the benefits you expect to receive from becoming an entrepreneur can serve as a beacon that guides you through the challenging moments. (Just as important: celebrating successes, no matter how small, as you achieve them).

    A few questions to help you maintain a balanced perspective:

    • How do you want to be showing up in the world?

  • What kind of impact do you want to make?
  • If today were the last day of your life, would you want to do what you are about to do today?
  • I suggest taking some time to think through these questions as you decide whether you want to transition from employment to entrepreneurship. If you're open to sharing, feel free to write me at thebusinessalchemist@gmail.com. I'd love to hear from you!

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