You’re Not Crazy, Quit Your Job

A special thanks to our sponsors for making this newsletter free for our readers:

It’s tough out there. CMO Huddles helps B2B CMOs gain the confidence, colleagues, and coverage they need to succeed. Ask Drew Neisser for a guest pass.

Need to hire a CMO or VP of Marketing? Want the ‘make money’ variety, not the ‘make it pretty’ variety? I recommend Erica Seidel of The Connective Good. Join her newsletter.

Entrepreneurialism defies human instinct, yet it’s addicting. Once you get just a taste of what life can be like with a future built on your terms, it’s game over.

There’s no going back to a 9 to 5—at least not without a persistent nagging in the corner of your brain that says, “I can do this on my own. I know I can.” I know the feeling firsthand, with 10 marketing roles in as many years to attest to the fact. Some positions included world-class benefits, stock options, outrageous 401k matches, remote world travel and six-figure salaries.

Even so, no full-time role in someone else’s company ever felt quite right. I itched to build my own business. During the rocky past three years, I’ve learned a number of valuable lessons that I believe can help anyone making the leap to create their own company.

Conquer financial fear.

Fear has been the biggest detriment to my success as a business owner. The rising cost of essentials such as groceries, housing, insurance, family, taxes … the list goes on and on. It’s no wonder so many innovative spirits are crushed by the pressures of modern society.

Fear is the paralyzing bane of the entrepreneur, and I’m guilty as charged.

For me, overcoming my fear and attaining financial security meant living well beneath my means. While my friends partied and went to bars, I stayed in, squirreled away spare change and worked as a freelancer. The key was changing my mindset to discover the bare minimum I needed to live on each month.

I spent three years working full-time while building my business. During that span, it was most important to:

  • Reduce monthly expenses by negotiating utility bills, rent and credit-card interest rates. I clipped coupons for groceries and calculated unit cost by the ounce to find the best value for my money.
  • Eliminate all credit-card debt. I used 0 percent balance-transfer offers to extend my grace period and avoid paying more than the principal I’d charged.
  • Battle the urges to buy a new vehicle or an expensive bottle of wine.
  • Earn repeat freelance writing clients to supplement my business.

You should aim to build up a security net that can cover your living expenses over a three to six month time frame.

Understand that you can be happy living on very little cash. To test your threshold, experiment with cost-cutting before you leave your full-time job. This can give you a better idea of how your lifestyle will look and feel when you’re a startup business owner.

Remove your ego.

I’m ashamed to admit it, but some sick part of me always wanted to earn more money than my parents. I was obsessed with money. Yet when I attained my first Director of Marketing title and oversaw large departments for a Fortune 500 company, I was completely miserable.

Money meant nothing. I didn’t know how many bosses I reported to or how many employees I managed. There I was, in my mid-20s, and I thought I was golden.

I felt disgusting.

To get beyond (some of) my ego, I began reading books about Buddhist philosophy, minimalism and meditation. I’d get my butt kicked at the gym—an incredibly humbling yet oddly rewarding experience. Most important, I carved out more time to spend with family and friends.

Eliminate your ego by putting others ahead of yourself, staying positive in times of hardship and being grateful for the opportunities you’ve been given.

Build relationships.

All of business depends on people. If you understand how to communicate your dreams to those in your network, you’ll discover mutual interests, form new friendships and create the right conditions to generate business.

Make it a point to:

  • Reach out to professionals by phone, email or on social media sites such as LinkedIn, Twitter and Facebook.
  • Organize coffee meetings—and since you’re the host, you always should cover the bill.
  • Attend industry events or local community gatherings.
  • Strike up conversations on airplanes, in long lines and in public.
  • Always give more than you take.
  • Seek and cultivate mentor relationships.

Build a network of people who believe in your efforts and whom you are proud to call your friends. Your support system is a crucial component to help maintain your sanity and build confidence as you invest in yourself and your dream.

Trust yourself.

You don’t need to be an expert in every aspect of business to be an entrepreneur. Are you worried about 1099 taxes or filing paperwork for your LLC or S-Corporation status?

You’ll figure it out when the time is right—and by then you’ll be smart enough to know when you need to enlist the help of a professional. You cannot afford to be paralyzed by the unknown.

According to self-improvement and leadership pioneer Dale Carnegie, “Inaction breeds doubt and fear. Action breeds confidence and courage. If you want to conquer fear, do not sit home and think about it. Go out and get busy.”

When something becomes a challenge, you must face it head on. If your challenge is becoming an entrepreneur, the time is now.

A version of this post originally appeared on Entrepreneur.

When you're ready, there are 4 ways I can help you.

Elevate Your Executive Game Join my exclusive coaching program and strategize with the top 1% of leaders. Outmaneuver competitors, secure coveted roles, and shatter compensation benchmarks.

Boost Your Brand to 10,000+ Executives Sponsor Execs and the City for unrivaled exposure to 10,000+ engaged executives and 32,000+ LinkedIn followers. Amplify your message and grow your influence today.

Captivate Your Audience Book me for keynotes and workshops that motivate. From influence and persuasion to negotiation and sales, I’ll deliver lasting impact. Inspire your team now.

Win High-Stakes Negotiations Founders, CEOs, celebrities, and athletes: gain a master negotiator’s edge in turnarounds, M&As, and major contracts. Secure optimal outcomes in any challenge.

Gain a competitive edge.
Join 10,000+ global readers receiving an original take on career strategy every week.


Share this Article