Ten Steps to Succeed When You're Feeling Overwhelmed

Updated: Aug 17


My father tells a story about how he succeeded in building what is now the highest earning property in the Starwood Hotel portfolio - the Westin St. John in the U.S.V.I. He states that he was capable of doing it because he didn't know he couldn't. While this sounds a bit lofty, and maybe even a tad arrogant, when probed futher, he'll quickly explain that what he really means is that he was too ignorant to know he couldn't. I can still remember so very clearly the day when he took me on the company boat from our property in St. Thomas over to the barren beach of the new development site on St. John. Standing there, in the sugar white sands of the shoreline around the small age of 10, I told my father he had to save the mongoose and the inguanas from what I was sure would be environmental destruction. Inspired by the worried request of a child, he enlisted the help of his crew, built big cages out of chicken wire and proceeded to catch every iguana and mongoose possible for transport to the national preserve round the other side of the island.


In the era of the 80s, sustainable economic development was a phrase no one used; rather, it was simply what you did if you wanted your hotel to stay afloat on a small Carribean island. With no internet or social media to rely on for marketing, industry relationships were key, as was good practices that treated employees with kindness, gratitude, and respect. In those days, not everyone was so easily replaced by a sea of thousands of resumes scoured by AI readers searching for key terms. Company loyalty was cherished, and businesses aimed to develop family-friendly environments where people could enjoy working. Now that I am grown, I wonder whether I will ever be able to attain even a fraction of the impact my parents had on the lives of so many others. I can't forget the story of one island waitress who, upon greetings my parents during breakfast at the seashore restaurant, expressed great gratitude and happiness that due to her employment, she was able to send her son to the best school on the island and that he was now doing very well. She said she was so thankful for her job and she just loved being there. It was then that I understood that how we treat others makes a major difference not only in their lives, but also in the lives of their family, friends and community. Having the real privilege of seeing first-hand how some folks achieve their success, here are 10 tips I have learned and regularly practice to keep going when I'm feeling overwhelmed.


(1) Feel a sense of urgency. What is driving you to develop your startup? Do you have a deep, unfulfilled passion to achieve something that's nagging away at you relentlessly? Are you desperate to escape the grind of never having quite enough, borrowing from one source to pay the other? Or is it more of a passing interest that occupies you on rainy days? My "a-ha" moment came when I realized that no one was going to save me. I wasn't going to figure out the stupid HR algorithm and land that big job, nor was I going to suddenly be let into the big-boys club, crash through gender barriers and be the next senior partner at the big law firm. Well, not before age 60. I was going to have to save myself. How desperate are you to change your destiny and what are you willing to sacrifice to achieve it? If your passion is more of a hobby than a pressing need, you're less likely to succeed.


(2) ALL your days must be filled with work with life tucked-in here and there. I didn't understand it until recently, but the life of a successful entrepreneur is their work. What this means is that if you are awake, you are thinking about work. When you are on a date with your significant other, you are talking about work. When your date goes to the restroom, you check your email, respond to messages and maybe sneak in a phone call. It means that the first place your kids look for you is the home office, and that the only reason you stay home from the real office is because you need some peace and quiet to turn on your super-productivity. The only reason you should be watching Netflix is to turn off your brain just long enough to get some sleep, but you check emails in the middle of the night when you wake-up to pee.


(3) Only include people who support your work-life imbalance. If you are doing it right, you are going to really annoy a lot of people with your work obsession. They will say things to you like "all you ever do is work!", or "you're such a workaholic!" Ignore them and allow them to slide gently from your life. You can't afford to spend hours each week on meaningless phone calls where you listen to your best of friend of 15 years complain about the terrible movie she saw or her latest bad date. You'll know you've made the transition when your friend texts you that she thinks you are mad at her because you haven't replied to her for three days. Embarassed, you quickly shoot back that you've simply been so busy that her text got shoved down to page two on your phone by incoming texts from others and you literally, simply forgot.


(4) Vacations = business trips with an extra day tacked on. You'll have achieved some semblance of success when the expectations of your clients, customers or staff depend so much on your participation that you simply, truly, cannot ignore what's going on at the business for a single, entire day. When you take your phone with you to the resort pool in a waterproof cover and respond to folks in spite of your out-of-office email reply, you're thrilled you actually have a business to manage. You start thinking about whether you can expense certain aspects of your trip if you toss in an hour of work here and there, and make a calendar reminder to call your accountant to discuss. Nah, you call your accountant now.


(5) Don't let your ego crash you. We've all heard that the definition of insanity is repeating the same steps while expecting different results. Regardless of your line of business, no matter the model, unexpected events will occur that cause you to have to rethink your direction and restart your engine. Get over yourself and pivot! All too often, entrepreneurs insist on forcing an issue, or they try to throw more money at a problem in the hopes it will disappear. There's even a famous song about this called The Gambler by Kenny Rogers wherein he sings "You got to know when to hold 'em, know when to fold 'em, know when to walk away, and know when to run." Take it from the good Kenny Rogers, throwing good money after bad seldom works. Stop the crazy and change your course. You can tell everyone about your perceived "failures" after you've achieved unicorn status.


(6) Tackle challenges like an NFL linebacker. Are you panicked by upcoming deadlines and due dates? Are you secretly freaking out that maybe you're a crazy person for even thinking this was possible? I teach my kids that bravery means you do it while afraid. We are taught there is this magic mental state called "fearless", but that's mostly crap unless you're a sociopath. The real truth is most entrepreneurs regularly struggle with fear, doubt, and yes, even crushing depression. The trick is to ignore it, or embrace it for a brief moment and then ignore it, but no matter what, you must RUN STRAIGHT INTO THE FACE OF YOUR DOUBTS! Crawling under your toasty bed covers and hiding from the challenge definitely won't make it go away. Taking a mental health break only brings the deadline closer. The only way to truly conquer a challenge is grasp it firmly and attack, refusing to lay it down until it is fully completed. I don't care if you're bawling your eyes out like a baby while you do it, as long as you're doing it.


(7) Don't fix it if it's not broken. When you figure out something that works, even a small something, like a customer favorite on your restaurant menu, don't fix it. I can't even count the number of times I have watched titans collapse because they had a great thing going, brand loyalty and quality standards, and then they apply a fix. Customers are furious; they feel like their trust has somehow been violated and they run screaming. When you land on something that works, leave it alone! Lather, rinse, repeat.


(8) Shut up and study, but accept you'll never know it all. The world is changing at a blinding pace. Short of a massive disruptive event like an EMP attack, the rate of change is not going to stop. In order to keep up with your industry, you must stay abreast of these changes and do everything you can to stay relevant or be left behind. This means you are going to have to study. Investors and customers don't care if you want to study or even if you like to study, they only care if you're relevant to their objectives. You must subscribe to industry journals, join associations and maybe even achieve a professional certification or a few. You'll have to work harder than you ever thought you could, and it may even make you a little furious for awhile, but it is so worth it. Sow your seeds of success today for a bigger harvest tomorrow. However, understand that because we live in the information age, you'll probably never know it all, and that has to be okay. Don't worry, as long as you keep at it in good faith, you'll figure it out. If you still have trouble, ask for help!


(9) Fair is for Kindergarten. When someone told me, probably my mother, "who told you life is fair?" I was stunned. I had nothing to say. No tawdry come-back, no wit at all. Guess what? Life is not fair and neither is business. Some crap competitor might get the contract over you, or maybe you feel like you've been overlooked and undercompensated because of some ridiculous, invidious discrimination. Trust me; I've been there, a lot. It sucks. It really, really sucks. Call your mom, your BFF or your significant other. Whine, cry, watch a movie or do an activity for a few hours, but never, ever quit. And, despite all the current social support toward embracing your feelings, don't share these feelings with your team, and certainly don't share them with your investors. To do so would destabilize their opinion of your professionalism and your steel will to succeed. Remember tip #6 "Tackle all challenges like a linebacker."


(10) It's better to have a piece of something than all of nothing. Don't hold your business so tightly that you suffocate the life out of it. I've worked with entrepreneurs who are so greedy for control that they only hire folks who are less equipped than they are, and if they are challenged, they make the environment so deragatory and depressed that these talented people walk out. Similarly, I've worked with entrepreneurs who are so greedy for the money, they price themselves right out of the market, scaring off potential investors and customers. Referring to tip #8, you must study your market, prepare your financial projections and value your business reasonably. Only a self-righteous fool prefers to own all of nothing rather than a piece of something.


So, there they are. Ten tips to succeed when you're feeling overwhelmed. While these are in no way exhaustive, they are real. And when your running a business, who has the time for fantasy? Refer to tip #2.

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