Realities of Leaving a Day Job and Pursuing Entrepreneurship

by / ⠀Entrepreneurship Startup Advice / January 13, 2014


If you’re an entrepreneur, no matter what industry you’re interested in, there’s a certain call that’s difficult to ignore. It’s the thrill of a new idea, the possibility of a product or service becoming a household name, the high of success…entrepreneurship truly is in the blood. However, for every wonderful thing that comes with being your own boss, there is a challenge to overcome. If you’re considering striking out on your own and trying your hand at entrepreneurship, it’s essential to go into it with the knowledge that there will be many challenges – both great and small – that will have to be addressed.

Leaving the Comfort Zone

The hardest part about becoming an entrepreneur is leaving the “Comfort Zone”.   No longer will you be relying upon another successful business to provide you with a monthly paycheck.    The fluctuation of your business and its growth will control what your take home salary is every year.

If this does not scare you, it should.   The process of becoming an entrepreneur is riddled with failures and learning experiences.  It is not uncommon by any mean to fail before succeeding in business.

There are very few people that can withstand losing months or years of pay pursuing a business that simply does not take off.    It is important to have a plan for failure, and of course a plan for success.   Be prepared for the business you are developing to take time to grow, and thus time to create a profit.

Reality check, Checked!

Once you have come to the understanding that this ride could get bumpy, it’s time to begin developing your plan for success.


With any great business idea, there is a need for capital to get it up and running. Start-up costs include things like product development, marketing and advertising budgets, store-fronts and more. Obtaining this financing can be daunting at times, considering most new entrepreneurs don’t have the funds on hand to cover those start-up costs themselves, and banks aren’t quick to give out loans to businesses that aren’t already creating an income. Although all businesses are different and may require different amounts of seed money, a Gallup Small Business Index Study suggests that the average start-up cost for a small business is $10,000.

When choosing a startup it usually is a good idea to start very small.   Dream big, but start small.  Choose a business plan that has a very small overhead and startup cost, which will allow your business to grow gradually and avoid large expenses that could quickly sink your entrepreneurial endeavor.

The Positive – The great news is that entrepreneurs no longer have to rely solely on small business loans or investors. Crowd-sourcing is a wonderful way to gather that initial investment in the business or idea, and websites like and are great places to start. These platforms allow investors of all kinds to help out a brand new business, with the promise of unique incentives.


Part of the thrill of becoming an entrepreneur is caught up in the risks you will take, and there is no great payoff without risk. Often times a new business is a huge gamble; you’re gambling with your own money and the money of investors, you’re gambling with your lifestyle and your family’s lifestyle, and with your own reputation. No matter how much research you do on a particular product or service idea, there’s no way to tell just how successful it will be until it’s launched and out there for the public to take advantage of.

The Positive – There are several ways to reduce the risks you’re taking when you start a new company. The most important thing you can do is research. Research the market, your competition, and every other aspect you can think of when it comes to a particular product or idea. The more you know about the possibilities, the better you will be able to guess the outcome.

As mentioned above, try to stay clear of startup businesses that cost a great deal of initial capital.   This allows for chance to fail and potentially bounce back, then trying again with a revamped idea.  It also gives a business breathing room to expand gradually, instead of immediately placing itself in a great deal of debt and having to struggle to keep itself above water.

Drive and Persistence

Not everyone can make it as a successful entrepreneur. Even with the best ideas, poor personal skills can spell quick ruin. As your own boss, you will need a certain amount of initiative to operate a company or manage a business idea. There is no supervisor reminding you of what needs to be done and how quickly it needs to be done. There is no team of higher-ups managing tasks that must be completed and the teams that will complete them. You answer directly to yourself and the expectations of those around you. This can be extremely difficult if you don’t have the right drive, persistence and mindset. Because of this, many companies and ideas with a huge amount of potential end up failing.

The Positive – You can teach yourself the skills you need to be successful. This includes things like organizational skills, time-management skills, setting goals and taking steps to achieve those goals, team-building and motivational skills and more. Consider taking classes designed to teach these techniques and skills; they will certainly pay off and you will continue to draw on the knowledge throughout your career as an entrepreneur and when interacting with others.

Find Mentorship

Find people that have been successful in the type of business you are pursuing.   It is important to find someone that can mentor you before and during your approach to this new business.  Find someone that has experience but is not in direct competition with you in your area.  Mentors are incredibly valuable and can allow you to dodge pitfalls, as well as keep you aimed and focused on the prize.

Many people that start businesses want to “reinvent the wheel” with their new business idea.   It’s important to base your business off a profitable model that has already worked,  this greatly reduces the risk of your start up failing.  Start by understanding your competition and how they have succeeded and then strive to be better than them through innovation.

Other Unique Challenges

There are many other challenges entrepreneurs face – from finding a balance between work and life to chasing down the payments of clients. Being willing to research, study and learn is a great first step in becoming a successful entrepreneur. Read everything you can get your hands on and be willing to try out different methods until something works. Accept advice from those who have been there and take notes when an entrepreneur you admire is speaking/offering pointers. Just remember that no amount of reading or research can truly make you successful until you’re willing to follow your dreams and take a leap of faith.

Jonathan Koenig is a small business owner in the U.S..  His expertise lies in start-up marketing, strategy, and development.   He currently runs and owns a Medial Assistant Training center and website in San Diego, California.

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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, 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.