The journey of entrepreneurship is a long and treacherous route towards absolution; but for the few who never give up, the rewards are vast and stupendous. “

Aidan Neal

Islanders are no strangers to entrepreneurship. With an unparalleled zeal and ingenuity, it’s no wonder that more Caribbean professionals are taking the plunge and using their wits and creativity to pave a way for themselves. Along that journey, there are several struggles every Caribbean entrepreneur knows all too well. Here are a few:

1. Tapering Risks

We all know that “you gotta spend money to make money,” But how much do you spend? How much do you risk. If you read enough books your bound to discover conflicting advice. Like Joy Mangano you could risk it all on one idea, put up your home and entire life savings as backative for the unwavering belief in yourself and your dreams. Or you could play it safe with meager financial contributions to your dreams, with the hopes of supplementing funding with good old hard work. Both are extremes, and both have their share of success stories, but the best approach is somewhere in between. In the word of the late Muhammad Ali, he who is not courageous enough to take risks will accomplish nothing in life.

2. Badmindedness

There has been a long line of crab-in-a-barrel mentalities within Afro-communities. The Afro-Caribbean community is no different. A lot of Caribbean leaders fail to see the value in uplifting others or joining forces with great minds to achieve amazing feats. Instead, we are more prone to tear each other down our withdraw our support. People give into jealous natures and while they may not make moves to sabotage another’s stride, they will do little to nothing to augment it. This platform of badmindness also stunts the thinking of an entrepreneur. It cultivates an environment where though one may not subscribe to those ideals, they may fear sharing ideas or offering too much of themselves because they are weary of others ill-intentions.

3. Deciding when to jump

It’s not unusual for the Caribbean entrepreneur to start their journey “late”. Getting a good education and thereafter, a good job has been instilled in us. As such, for a lot of island entrepreneurs,the jump into self employment tends to come after we have established a sense of security. Experts are now saying that the concept of taking great risks to reap great rewards is now an obsolete one. Taking a life vest with you, doesn’t mean you’re not serious about the plunge. But you must jump. If you find yourself spending more time building safety nets than making moves towards your financial freedom, then you’re not serious about your dreams.

4. Lack of Mentorship

This struggle echoes not from the unavailability of mentors but the unwillingness of many to do so. If this is false, the compelling truth is that enough believe it to even attempt seeking mentorship within the Caribbean community. Success is seen as something that is coveted and owned, instead of as a platform to serve. Instead of asking ourselves, “how can I be of service to this person, and they in turn to me” we instead ask, “what are they up to?” “Will my mentorship put them in a place to surpass me?” “Nobody neva help me reach this point, why should I be shelling out handouts.” All these, miss the point entirely.

5. Living to work vs working to live

Island life is pretty laid back. I remember that if it was raining too hard, that was just enough cause to skip school. To this day I have friends who leave work midday for hair appointments or to get their cars washed. Living in an overworked society can give the false impression that this is laziness. It’s not. We grow up with a true value for quality of life. We learn early to tie our happiness to experiences and the ones we love. Being an entrepreneur requires more time and sacrifice of self than any one could imagine, It calls for the sacrifice of experiences, of time and often the quality of relationships. The internal struggle one faces as to whether they are living to work, or working to live is even greater for the Caribbean entrepreneur.

6. Being Undervalued

Those who don’t want a handout, feel entitled to a discount. The Caribbean entrepreneur is plagued with a community of persons who ask, no matter the quoted price, “u cyan work wid me?” or “a so you dare?” Everybody likes a deal, and it is a consumer’s due diligence to ensure that they are getting a fair break. However, we seem to miss the importance of supporting others and truly understanding the value of the work others provide. Nothing is wrong with an educated negotiation but the expectation and immediate swindling can be quite disheartening. If you’re a consumer, be mindful of this. If you’re the vendor then ensure the price points you set, consider comparables as well as the value of your time and creativity.

7. Jack of all Trades….Master of some?

There’s a running joke about Jamaicans and their propensity for holding down several jobs. And it’s pretty much true. We’re very hard workers and it is not in our nature to explore only one facet of our being. For those of us who have talents beyond the skills required for our careers, it comes naturally to put those talents to work. In Steve Harvey’s Act like a Success, Think like a Success, the author encourages us to identify the specific talent, that when monetized, can lead to our financial goals. But what if you’re multi-talented? What if more than one of your gifts gives you purpose? How do you decide what gets your all? For the islander, because of our work ethic and drive, we may decide to pursue them all, playing a juggling act and undoubtedly never mastering them all. You don’t have to commit to one thing at a time, but you can’t stretch yourself thin and expect life-changing results. Find a way to prioritize and budget your time appropriately.

8. Losing Steam

The struggle of every entrepreneur is being consistently motivated. When we get started we are so very inspired. A fire is lit under us and we take on our dreams with vigor and decisiveness. As time passes and we encounter more challenges than successes, we tend to lose steam and have to dig even deeper to find that drive we once had. The key is to mastermind your failures. To be grateful for the lessons that come with them and to keep going. The only way to truly fail is to give up. You won’t be motivated and excited everyday, but you have to keep going. You’ll find renewed motivation on the way.

9. Unsolicited Advice

Islanders all seem to have a certain arrogance (the degree of which, differs, depending on one’s nationality). Caribbean entrepreneurs, despite their success and levels of accomplishment will be constantly vulnerable to unsolicited advice. Everybody knows something about everything. And whether or not you asked for it, their nuggets of wisdom are coming your way. Never be so arrogant that you fail to listen. Everyone can teach us something, even if that something is how to tune out people.

10. Not Communicating your Value

Not wanting to show off has its place. But in business, there is a delicate dance between humility and being able to speak to ones talents, accomplishments and capabilities. You’re in a game of competition and the person who can best articulate their value wins. Mind Tools and Entrepreneur magazine offer valuable succinct steps on how to perfect your elevator pitch. If you can’t sell yourself, you won’t earn an opportunity to prove just what you can do.

Tell us about your struggles! We wanna know what aspects of entrepreneurship plague you?


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