Red Responds: Longing to Be an Entrepreneur

Lynn in Beverly Hills writes:

I’m trying to decide whether to keep my well-paying job in corporate America or to start my own business. I enjoy my current job but I long to be an entrepreneur and do something totally different. I worry about giving up the lifestyle I’ve become accustomed to and more importantly that I may not be able to continue setting myself up for a comfortable retirement. what do you see?


Dear Lynn,

If you were to quit your job and go full swing into an entrepreneurial position, the experience through your eyes, could be classified as falling flat on your face. It’s not because you won’t achieve success on your own because you will. But, the initial transition comes with the consequence of working twice as hard for half as much and it will reflect in your financial portfolio. You would do much better than simply recover from this in the long run, but I have concerns on how you handle the stress during the journey.

Even if you were to buy an existing business, the transitional period is going to be tough on you. You are not a foolish woman. You understand that it takes money to make money but your projections, in any scenario, are coming through as “off” in terms of the return timeline. Ironically, it is not due to fault or flaw on your part, it is more massive – an economic shift that is just enough to screw up your plans and kick in your neurosis. What it all boils down to around you, is a timing thing.

I am not trying to discourage you from catching your dream – it can become a reality. I do, however, want you to rethink your methodology of making this transition. All the way around, you seem to benefit more by starting your business before you quit your job. Unless you are mentally and emotionally prepared to change financial lifestyle, your best approach is to play it on the safer side of things by not going “all in” in one fell swoop.

If you have to take an “all or nothing” approach, you need to wait at least a year and a half before you can do this with relative ease.

You have a talent for thinking outside of the box, and you definitely aren’t afraid of hard work. Follow your creative spirit. That is where your happiness, not to mention your money, flourishes and grows.

Brightest Blessings!

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