Shaping your career is a lifelong process by Sam Shanck, CEO HOTEL TONIGHT

Shaping your career is a lifelong process by Sam Shanck, CEO HOTEL TONIGHT



Shaping your career is a lifelong process.


Many of you want to start a company. I certainly did. But I knew I wasn’t ready when I graduated.


You probably think starting a company is risky. When I started my first business, most of my friends thought I was a crazy risk-taker. I couldn’t disagree more—I had raised money from my family and wouldn’t be financially ruined if I failed. That would be true risk. That said, I did put my reputation at risk, especially within my family, who were people I desperately didn’t want to disappoint. While I didn’t feel risk, I felt an immense amount of discomfort and stress.


The key skill you must master for life as an entrepreneur is to be comfortable taking calculated, or safe, risks. I call this feeling “being over your skis.” It’s the feeling of losing control when you’ve hit a jump and are flying through the air. Worst case? You’ll land in powder and have a bruised ego. But you’ll emerge a stronger skier.


Prepare yourself now by always being slightly uncomfortable. Make career choices that others view as risky, but that you know have limited downside.


Start small in taking safe risks by interviewing for a job you know nothing about. Or by emailing people you admire and asking for an informational interview. Then move on to volunteering for a highly visible project in your company. Challenge yourself to find discomfort by focusing on your weaknesses. If you’re not good at sales, find a way to start selling a product or service at your company. If you’re intimidated by technology, teach yourself to code and ask your CTO to review your work.


I practiced taking safe risks until the discomfort of starting a company was just bearable enough that I could actually do the work of starting a company.


By the time I asked investors for hundreds of thousands of dollars in seed financing, it was stressful but not paralyzing.


The best part about learning by taking smart risks and staying uncomfortable is that you’ll always emerge stronger. This will help you have a better, fuller life, even if you never actually want to start a business. Ultimately, the real risk in life is that you’ll depart this world not accomplishing what you want—and what you are capable of doing.


Take risks. Find satisfaction in staying uncomfortable. Turn your ability to endure risk into your confidence as an entrepreneur. You’ll be amazed at what you will accomplish. I, for one, can’t wait to be your customer.