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Lessons Learned in My First Decade of Entrepreneurship

Posted January 30, 2017 in Career Management, Latest News & Insights, Self-Insight

My birthday was this past month and this year it was a bit of a significant milestone for me. You see, exactly 10 years ago today, I had my last day as a full time employee. I remember walking out of the office (frantically throwing to-do lists at everyone in my path) completely unsure of what I was about to step in to. No plan, no income, no severance, no sugar Daddy, no safety net of savings. It’s hard to believe that it’s been 10 years, but in that time, here’s what I’ve learned:

  1. You can do more than you think you can do. Everybody is scared shitless and feels like they don’t know what they’re doing. The difference is that they lean into the fear and push forward. I have to continually remind myself of that fact… but my fears are getting more and more manageable.
  2. When other people believe in you, believe them. Period. We often hold ourselves so much smaller than we have the potential to be. Listen to those around you and surround yourself with people who believe in you and will support you.
  3. When you leave your fancy post with the fancy title, you’ll really see who your real ‘friends’ are.
  4. There’s a lot of bullshit bravado in the entrepreneurial community that you don’t have to subscribe to. You don’t have to sacrifice your family to build a business.
  5. There’s no such thing as perpetual career bliss. Even when you genuinely love what you do, there’ll be good days and bad days and days that are simply ‘meh’.
  6. Comparison to others is never healthy. You will face disappointment, rejection and possibly even have people do unethical things like rip off your clients or your ideas, but…if you continue to care about the work you do and the people you work with…none of that stuff will really matter. You will keep going and growing and making a difference.
  7. ‘Talk does not cook rice’. Neither does a slick website or cool marketing collateral. Building a business (like mine anyway) is 100% about the hustle.
  8. You can have too much of a good thing. Shiny object syndrome is a real affliction and one best controlled by surrounding yourself with people who don’t think the way you think. I’m grateful for all the amazing people who have worked with me at The Roundtable over the years and kept me on the straight and narrow (for the most part anyway!)
  9. Being an entrepreneur is the most stressful job in the world. There is never a ‘steady state’. You will worry about making payroll, you will worry about where your next client project is coming from, you will worry if your new team member will work out…it’s endless. Sometimes a steady paycheque is so much more appealing but…
  10. Being an entrepreneur is the most amazing, rewarding and exciting career in the world and has given me the opportunity to connect with so many amazing people. I wouldn’t trade it for a second and only wish that I’d had the belief in myself to start the journey sooner.

If you’re someone who is thinking of taking a leap into uncharted territory…whether that be self employment or a career change via a new job or industry…remember… we are much more likely to be driven by our fears and that’s what ultimately holds us back. I hope you found this post to be a bit of a shot of inspiration that encourages you to pursue whatever dream you might be chasing.

Happy leading!


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