When Jason asked me to contribute to the blog for TravelHost I thought about how I started going from employee to entrepreneur and the changes/impact it would take on my life. I wrote this article back in September 2015 and it still resonates today. When you decide to take the leap of faith and become a publisher in the TravelHost network keep this in mind as you transition from employee to entrepreneur.


I would like to tell you that this post is coming from a place of well earned wisdom but the reality is — I’m in the thick of it.  A little over four weeks ago I took the biggest leap of my life. I opted out of my 18 year corporate career and said “HELL YES” to entrepreneurship.

When I exited the building for the last time, I had grand plans of how I would spend my first weeks of full time entrepreneurship. No longer having to squeeze my work into ill fitting time slots, I was ready to hit the ground running. It was going to be graceful and gazelle-like.

But it wasn’t. I hit the ground and face planted!

After two weeks of fighting what was happening, I chose to surrender and give myself whatever time I needed. Instead of digging deep and pushing through, I took a step back. Perspective was gained and wisdom has started to trickle through.

If you’re going though a significant life transition with mixed up mojo, don’t fret. Deep breaths and try some of these things to reclaim your sense of self.

31 Things to Do When You Transition from Employee to Entrepreneur

  1. Acknowledge the MAJOR life change. This is going to have a HUGE impact on your life.
  2. Give yourself the space to figure things out.  This might be a good time to plan some business activities that allow you to downshift a bit.
  3. Find your full time entrepreneur flow. You’re programmed to be working all the time if you were setting up a business while working full time. It’s time to stop grinding.
  4. Build your new routine. You no longer need to crack the laptop at the crack of dawn and guzzle your coffee as you’re rushing out the door.
  5. Take some time to visualize your ideal day.
  6. Get to know the REAL you. The one that no longer needs to split personalities between work and life.
  7. Let go. Scary, yes but so worth it.  You will be OK. Let go of whatever you need to and start fresh.
  8. Forgive. Depending on why you are making the leap, you might have some forgiveness work to do. Were you bullied or treated poorly? Maybe you were underutilized or undervalued?
  9. Express DEEP gratitude. Were there people who supported you along the way? Put up with your crazy work hours? Took a chance on you and gave you business?
  10. SLOW down. You ditched the rat race for a reason. Savor where you are.
  11. BE present. This time can be anxiety producing and you might want to numb out. Stay present. Whatever you are experiencing will become a part of your story — make it a good one!
  12. Welcome making new connections. Building quality relationships are key to building a business — especially when you’re on your own.
  13. Celebrate!! Keep celebrating. These first few weeks and months can be harrowing or they can be the best of your life. You get to choose. Choose to celebrate.
  14. Shut out the noise. Now is NOT the time to be comparing yourself to others. Stay focused on your accomplishments. Heck, you just achieved a MASSIVE goal. See #13.
  15. Create space. Get intentional with your calendar and build in plenty of margin.
  16. Schedule time daily to work on your mindset.
  17. BELIEVE in yourself. Create beliefs that support your vision and goals. Root them deep in your being.
  18. Suspend judgement. However long it takes to move through this transition is how long it takes. There is no right or wrong way to do this.
  19. Do something really out of your comfort zone. I realize that ditching your steady paycheck feels super scary but do the next scary thing.  Ah, perspective.
  20. Focus on abundance. Work on your wealth consciousness and keep your money mindset in tip top shape. Thinking about scarcity and “needing” clients is a good way to stop the flow of business.
  21. Regain clarity. You have achieved the freedom and control you wanted. Now what? Take some time to get clear on what’s next.
  22. Declare loudly and often  how much you love your new life (because it’s pretty damn amazing!)
  23. Declutter, purge, and clear old energy. Trust me…let it go.
  24. Focus on ALL the positives.
  25. Find a hobby (this is the one I’m most excited about!).
  26. Plan small incremental upgrades to your life that make you feel like you really are in charge of your own future.
  27. Feeling aimless but not ready for another ENORMOUS goal? Set smaller goals or create a mini business bucket list with quick hit items.
  28. Be kind to yourself. Now is a great time for self-care and self-love.
  29. Allow yourself to feel “all the feels” — the happy/sads and the scared/exciteds.
  30. Be flexible. You have most likely been on a rigid schedule to get everything done in life, work, and business building. Do things different. Try something new. Break away from the rigid schedule. You will survive (I promise!).
  31. Trust the process. Just go with the flow.

For the Unapologetically Ambitious (like me)

This list is not your new conquest. These are merely suggestions on how you can spend your transitional time in lieu of freaking out about EVERYTHING. There is another way. It’s possible to ease through this transition and emerge deeply rooted in your new vision.

You are exactly where you are meant to be. You might as well enjoy it.


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Jason Bahamundi

VP Sales and Marketing at TravelHost
I have spent my entire career in the multi-media industry with experience in broadcast/cable TV, Radio, Print and Digital. Developing and executing a marketing strategy is my passion, but not my only passion as evidenced by my Instagram page. I love cooking and fueling my body for endurance sports through a plant-based diet. When I am not working on multi-media marketing, swimming, biking, running and cooking I can be found sharing laughs with my wife and step-son.

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