Two Entrepreneurial Takeaways From International Boost Your Self-Esteem Month


Regardless of age, gender or the size or age of their companies, the one single factor driving most entrepreneurs is their desire for autonomy, according to an Inc. magazine study from a while back.

Indeed, believing in your cause as a business and entrepreneur – and believing in yourself – is not only an important factor in your endeavor, it’s necessary. This dynamic is something to ponder when considering February’s International Boost Your Self-Esteem Month.

Self-esteem – sure. Self-confidence – absolutely. Heck, perhaps a bit of cockiness may serve you to an extent during that first big leap of faith in the life of your business – the start-up phase. In the beginning, doubt about what you’re doing can be paralyzing. Starting off, an entrepreneur may be bound to make a mistake or overlook a better way of doing something, but it’s better to make a call and believe in it than to exist perpetually in uncertainty.

However, there comes a point when you, as a business leader, have to understand how your roles may have changed in the life of the enterprise that you created. Unfortunately, just as a mother may not want to let go of her offspring, an entrepreneur may not want to yield control of the business to others – even when it’s clear that the business would be better off with delegated management.

This is the premise of my most recently published business leadership book, “The Second Decision: The Qualified Entrepreneur.” It’s so important to be able to identify which phase of your business’s life-cycle you’re in. As I’ve mentioned in prior posts, “The First Decision,” in which you were inspired to pull the trigger on a brilliant idea, start up the business and see its fruition, is the honeymoon phase. But as we know, honeymoons do not last forever. Even the most passionate love affairs must deal with a cooling off period in which life returns to a more normal and predictable pattern. You have to adjust to a second phase if you want to make the relationship work in the long term. Likewise, there is a time where you must adapt to what your business needs. This is what I call The Second Phase.

So, I offer at least two entrepreneurial takeaways for your self-esteem. First, take stock in what you’ve created. Great job! It’s not easy to invest time, effort and capital on your entrepreneurial dream. You’ve not only done well for yourself, you’ve likely also created jobs for others. This leads me to my second takeaway: don’t cling too desperately to your baby. If you cling too tightly, you may choke it, either compromising the enterprise’s well-being, or killing it. Your self-esteem and confidence should be sufficiently high. When you’re able to see The Second Phase, be honest with yourself. There will probably be portions of the business that are better delegated to others.

Whatever the assessment brings, realize that The Second Phase is a good thing. You’ve made it this far, and now you may have time for other things, which may very well include continued leadership in your business’s trajectory.