5 Tips on Becoming Your Own Boss

Posted by on Feb 28, 2014 in Our Journey

In the early days following my initial decision to start Slipstream it was surprisingly easy to stay busy. The problem for me was the feeling of uncertainty and not knowing if all that was keeping me busy was actually helping me reach my goal. Unlike my job in finance, there was no structure, no deadlines, no manager; it was just me. I have never been skydiving, but I imagine the feeling is similar. It is exciting beyond words and at the same time you are filled with fear. The prospect of returning to your old career stares you in the face, tempting you to choose safety over uncertainty, but once you make the leap the only way to control your path is to stay the course.

To be happy as your own boss you need to quickly get comfortable being uncomfortable. Working for yourself requires a whole new way of thinking about success, productivity and objectives. Below are a few guidelines that helped me out early on:

1)   Define Success. Any journey is easier when you have a destination. It gives you purpose and a path to get back on when you inevitably stray in the wrong direction. When you define success it makes it real and to me this was the true beginning.

2)   Break it Down. I quickly learned that focus on the destination without considering the path can be overwhelming. It is extremely important to identify the major milestones needed to reach your goal. These milestones should be measurable, large enough to matter and small enough to digest. For example, instead of “learn about coffee” I set milestones like “complete barista training course and learn major coffee varieties and processing methods”. Learning about coffee is something I hope to continue throughout my entire life, but the later goal is a box I can check.

3)   Take it One Day at a Time. Remember you are self-employed, not unemployed so treat each day like a real workday. Set a schedule and stick to it. Start every day with 3-4 achievable tasks you have to complete before you go to sleep. Completing these small tasks each day will keep you productive and the consistent progress will help you sleep at night.

4)   Find Support. When working for yourself, it is easy to take it to the extreme and keep everything inside in fear that others may see your mistakes and failures. It feels safer to limit exposure until you are closer to your goal. The problem with this thinking is that it makes it exponentially more challenging to actually reach that goal. If you made the tough decision to go after your dream, have the confidence to let others in and ask for help. Support can mean friends and family to help keep you sane and hold you accountable or it can mean leaders in your field that are happy to share their experiences.

5)   Expect Change and Adapt. No matter how well you plan, you will face many unexpected obstacles on your journey.  These obstacles could be external (e.g., a funding source falls through or you fail to get a permit) or internal (e.g., you realize that your plan requires several steps that you did not originally anticipate). Regardless, please remember that this is an unavoidable part of your journey and use your planning and support network to adapt. While your milestones may shift, it is important to stay focused on your primary goal and not let roadblocks knock you off course.

Hopefully the above will help you as much as it helped me. As I work towards my goal of opening Slipstream, I will continue to share the lessons I learn along the way. If you are experienced at being self-employed, please share any tips you have found helpful.

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