When Should You Become an Entrepreneur?

by / ⠀Startup Advice / June 2, 2022
bungee jumping

There’s no better time to become an entrepreneur. With more free and low-cost resources available to small businesses than ever before, there are no excuses left for not jumping in. Free communication tools (Skype), free document sharing and storage (Google), peer-to-peer business loans (Kiva) and affordable labor (Craigslist, Elance) make getting the guts to go for it the only thing left on the list. So what are you waiting for? Still considering all the “what-ifs?” Let me help you get over them.

What if I Fail?

All the “what-ifs?” really boil down to one question: What if I fail? Here’s the answer: everyone fails now and then. Even the most successful entrepreneurs experience a few failures. What makes them different is they learn from them and move on.

Three years ago, with the encouragement of my now husband and business partner, I took the leap, leaving traditional employment for the life of an entrepreneur. It was quite nerve-wracking at first (it took about a year before the sight of a business logo didn’t induce a whirl of anxiety and self-doubt) but I kept pushing through it. Today I can honestly say that it was the BEST DECISION I’VE EVER MADE. While I enjoyed my work in the past, today I experience more freedom and self-fulfillment than ever before.

How did I do it? To say it was easy would be a lie. Nothing worth having is ever easily attained. That said, it hasn’t been much more difficult than working for someone else. In fact, whenever I had doubts about my ability to succeed as an entrepreneur during those last few weeks as an employee, I reminded myself that if I put half as much effort towards my new business as I did towards being a great employee, I would surely succeed as an entrepreneur. And I have.

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Instead of asking yourself, “what if I fail?” ask yourself how you will succeed. Write down your goals and how you will achieve them, and get started on the first steps today.


How I Made the Leap

My husband and I were contemplating leaving the San Francisco Bay area in order to be closer to our families and buy a home, something we didn’t see as a possibility in the near (or distant) future in the evermore expensive California. I couldn’t imagine working for anyone other than my current employer – a well-known tech company where I had done well for myself as a PR manager, built solid relationships and actually enjoyed the work, despite the high stress level.

My husband had been working for himself as a graphic designer and Internet marketing consultant for several years, and he suggested I give consulting a shot. We could partner and offer all of our services under one umbrella. As soon as we discussed it, I thought, this could work. I know a number of professionals through my work at various companies who would recommend me to their colleagues and maybe even hire me themselves – I’ll give it a shot!

We told our friends and colleagues of our plans, and before we knew it we had more work on our hands than we could handle on our own. We began to hire other consultants to work with us who had similar work philosophies to ours: good work can be done no matter the time or location, as long as we meet client deadlines and expectations. Thus, our virtual PR and Internet marketing agency was born.

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Why Being an Entrepreneur Rocks

Today, we enjoy the freedom and flexibility that working at a bigger company simply does not afford. My husband and I take regular trips to our favorite places around the country, sometimes follow our favorite bands, taking our work with us, if necessary, on our laptops. We make the most of business trips, adding on a few days before or after to say, go skiing in Tahoe or tour around Europe. While we are always available during business hours so clients can reach us when they need us, we often take breaks during the day to go bike riding, fishing or head down to the beach for some fresh air.

Because our line of work (consulting) can get pretty time-consuming, we’ve launched other projects designed to reduce our dependence on our time as currency. For example, we have a janitorial supply business called Stock and Supply. We’ve set this business up to be as automated as possible – we don’t handle any actual inventory – and for a few minutes each week we are able to bring in a nice supplemental income. Working for ourselves affords us the time to create these additional income streams so that one day, we may not have to put much “work” time in at all.

You Can Do It, Too

The great thing about living in these times is that the possibilities for income generation are literally endless. The Internet makes it easy to research a market, find free and low-cost tools for getting started and just dive in.  The Web offers more free business advice for entrepreneurs than one can possibly consume. On top of this, new communication tools and mobile wireless cards have made it possible to do business from anywhere — like the backseat of a car or a poolside bar ;-).

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My recommendation to anyone thinking of making the leap is to jump in! You won’t succeed if you don’t try. And if you fail, you’ll find a way to get through it, learn from your mistakes and give it another go. No one gets it right all the time. If you pride yourself on doing a great job at what you do and if, when you look at your current job, you think – geez, if I put this much time and effort into my own business, surely I will succeed – then you have everything it takes to be an entrepreneur.

Good luck!

Author: My name is Ali Croft and I’m co-founder of Just Drive Media, a virtual PR and online marketing firm.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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