Taking The Leap (Two Essentials)

Shannon was fifteen years deep in her career. She stayed late, got to work early, and opened up her laptop on the weekends to help get ahead.

Then she received a summons that she was under investigation. Her boss issued the investigation that would eventually lead to Shannon quitting her job. She left her steady job, wrote a best-selling memoir, and became her own boss as an entrepreneur.

An inner city teacher in New York City, Shannon spent hours planning out lessons that would empower students and get them excited for learning. After finishing one particular project, her students were so excited that they suggested the class have a group hug to celebrate their success.

That’s when her boss walked by and felt she may be crossing the line.

Even though Shannon was found to be completely innocent from inappropriately socializing with students, the investigation left a scar so deep that Shannon knew it was time to leave.

She could no longer be comfortable at work.

The investigation caused Shannon to really examine why she was doing what she was doing. She knew she wanted to have a positive impact on students and help them live remarkable lives, but felt she was being held back.

The school system, which she had been frustrated with long before, needs some serious transforming and Shannon knew she could better empower students by pursuing her entrepreneurial dreams outside the classroom.

She went on to write, My Last 40 Days, and created The Transforming Public Education Podcast. She now works as a marketer for progressive schools to help them get their word out.

As a bonus, she’s free to travel where she wants when she wants and she no longer feels stifled by a bad boss.

Unfortunately, Shannon’s story is not that unique.

I’ve interviewed quite a few people who had to leave their corporate jobs because their boss created an unsuitable environment to work.

You may remember Ayelet Baron, for instance, who proudly fired herself from the corporate world after spending nearly two decades shouldering the tight deadlines and impossible travel schedules created by corporate bureaucracy. She now works on her own as a speaker and consultant.

I’ve struggled with this too. I have been teaching for almost a decade and love seeing the daily impact I’m able to have in helping teenagers pursue their dream career.

Sometimes I question leaving my safe full-time job to further grow The Traveling Cup and my writing and speaking career. Like Shannon, I wouldn’t leave teaching unless I knew what I was building would help empower millennials more than my full-time teaching job.

Thankfully, unlike Shannon, I have a great team to work with. I am also incredibly grateful for health insurance to help my wife battle Lyme disease.

Taking The Leap

If you too want to take the leap, here are two things to take with you.

1. Accountability Group

You need to surround yourself with people that will empower you through the transition. Jim Collins, in his book Good to Great, said that once you know where you’re steering your bus (read “your business”), you need to bring the right people on the bus. A screaming group of negativity will only cause the ride to be full of stress and potholes.

A bus full of people who empower you, offer solid criticism in a warm yet honest manner, and keep you moving forward is what you want.

2. Coach/Mentor

Hiring a solid coach or mentor you can have on speed dial can help you be more efficient. You can get something down in two months with a coach that may take you two years of making mistakes if you did it yourself.

When I was a personal trainer and triathlon coach, I was able to get people ready for a triathlon injury free in the best shape of their life and help them set a personal record far faster than if they trained by themselves.

A coach is a guide, an accountability partner, and expert troubleshooter.

I have both a coach and a mentor and they have helped me be more efficient and grow far more than I ever could by myself.

What about you? I’d love to hear your story. If you’ve taken the leap into being an entrepreneur or are questioning it, reach out and say hello (mark@thetravelingcup.com).

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