How to Win Against All Odds

Jeremiah Ajayi
11 min readOct 27, 2021

It has been exactly 50 days since I received a message that made tears flow down my face like a river escaping a dam. A feeling of disorientation overburdened me as the betrayal sunk in slowly. And when it did, I railed against myself for not taking the initial warnings seriously, exclaiming, “I should have known!”

Indeed, the signs were right in front of my nose. But I didn’t expect their manifestation to be this sudden and embodied in fake empathy. This surprise caused a sting of melancholy similar to how my first heartbreak felt.

This time, however, it wasn’t a girl who shattered my heart. Instead, it was my employer. His message was a termination letter firing me and implying I was an intern all along (even though our contract stated that my role was full-time).

Considering how supposedly well I had done my job, the dismissal was unexpected as snow in August. It was yet another depths of despair in what has been a horrible year.

My response to the termination letter

After getting laid off, I struggled with self-acceptance. I stopped applying for opportunities and paused my newsletter. After all, what’s the point in motivating others when I lack motivation myself? I couldn’t write well as my creative ink became hallow and dull.

Getting fired uncovered every wrapped emotional bruise suffered in 2021 — from toxic workplaces to a struggling freelance business, friendship breakups, numerous job rejections, and financial loss. So I took a break.

During this break, I ranted to a friend (Fola) who gave helpful advice. But whenever I tried to implement it, my inner voices accused me of being a loser who couldn’t handle an opportunity without jinxing it. It wasn’t until I spoke with Ayomide Ofulue before I could overcome that self-doubt.

Speaking to Ayomide revealed that I was unhappy because my self-worth was directly proportionate with my wins. It was this tendency that made this year’s dry spell deteriorate the silk of my happiness.

After that epiphany, I started to apply specific tips that have helped me become happy, resilient, and victorious. Even though I’m nowhere close to my dream destination, this is the happiest I’ve been since the year began. All thanks to the strategies outlined below.

1. Uncover the root cause of your unhappiness

It is easy to attribute our unhappiness to our non-achievement. This, however, isn’t always the case. Sometimes, our unhappiness is a symptom of a bigger problem. So even when we achieve our goals, we still feel a void in us. We remain empty even when we achieve our deepest desires. This was my situation.

I always thought I was unhappy because I hadn’t won this year. But while there was an element of truth to this, my conversation with Ayomide revealed the full truth. I was sad because of how I based my self-worth on my achievements — an unhealthy validation that stemmed from my childhood.

As a kid, I was diminutive, unathletic, and untalented. My intelligence and people skills, however, made me socially relevant. Flash forward to high school, I was an outcast in the midst of the other boys. Yet again, my outstanding performance made me popular and accepted even among cynics. This affected me as I began to believe winning is the only route to acceptance. This explains why I pushed myself to bag 30 certifications and took several jobs even when my plate was full. It is why I constantly worked hard to prove to others that I was worthy of embrace.

When I uncovered this root cause, I took the following steps:

  1. Created a list of the things I love about myself (e.g., my kindness, good-heartedness, listening skills, etc.).
  2. Defined what success truly means to me- impacting others positively. My greatest happiness lies in making other people happy.
  3. Reflect on the part of me that stays constant whether I win or not.
  4. Acknowledged that I deserve love no matter what I achieve.

The root cause of your unhappiness might differ from mine. But you would never know until you introspect. Sit down to think, “why am I miserable?”

2. Acknowledge the indispensability of luck

You need other factors apart from hard work to succeed. This is where luck comes in. And just as Oprah Winfrey defines it, luck is when opportunity meets preparation. So before you beat yourself for not achieving your goals, ask yourself, “How prepared was I? Was the opportunity right for me at the time? Were there contributing factors beyond my control?” If your answers proved that you were simply unlucky despite doing your best, give yourself a break.

Many a time, luck doesn’t shine its light upon you until your effort has compounded. On other days, it doesn’t matter how hard you work; life doesn’t just favor you.

Although that’s the harsh truth, you can get luckier if you apply some of the steps Max Gunther shared in How to Get Lucky:

  • Balance luck with planning

You must recognize the place of luck in success if you want to win in life. Nonetheless, luck won’t always determine your outcomes. There would be periods where planning is necessary. The secret is to know when to leverage either of these factors. “Is it possible to rely on your own or other people’s planning in this situation? Or is the outcome unpredictable and highly dependent on luck?” Ask yourself before you take any decision.

  • Build a quality social capital

Other people need to know what you do and how they can help you. This is how you get life-changing opportunities. I owe more than 70% of my past roles to my network. You, too, can enjoy similar advantages. Surround other people and be present where things are happening. If you don’t know how to cultivate your relationships, these tips will help.

  • Be prepared to take calculated risks

Good things happen to those who are willing to take risks it all. Max best quips this idea:

“One trait of the consistently lucky is that they can assess risk-reward ratios even amid confusion and ambiguity.”

Successful people excel because they know when to stick out their heads a bit, act on speculation, or avoid risks altogether. A lucky person is often in between the two extremes.

  • Anticipate catastrophe

While it feels great to be optimistic, hope isn’t a strategy. So you need to always prepare for the worst whenever you plan. Before you execute, ask yourself, “what’s the worst outcome that can happen?” In the event of this adverse event, how will you turn things around? Or like Max said, “And if the worst does happen, what will I do to save myself?”

  • Realize that not every event is meant to teach you a lesson

In your lowest moments, you might want to make yourself feel better by trying to see the lesson in your failures. But this isn’t always the case. Sometimes, rejection is just rejection. There is no lesson to learn. Lucky people know this and move on from their losses quickly.

These tips work as they helped land my new role at Victor Eduoh Consultancy (VEC) without applying for it.

This is luck in action as:

  • The opportunity landed in my laps: I had no intention of reaching out to him for a job. The coffee chat invitation was to learn about Victor’s processes (FYI: He’s a writer I admire). I didn’t intend to work at VEC
  • I was prepared: Although I had never planned to work at VEC, I prepared for it all along. I have consistently written online, delivered value in my previous positions, taken online courses, and expanded my network in the past years. These attracted Victor to me as he saw me as a valuable addition to his team — a major reason why he reached out.

3. Reframe your perspective

Instead of resorting to the victim mindset, try to change how you interpret your problems. Replace the thought of feeling cursed with ‘maybe the universe is trying to teach me something.’ Although this tip is counterintuitive to the previous sub-point, it’s effective.

Perhaps you’re not landing that job despite being technically ready because you’re not emotionally intelligent to handle it. Maybe you lost that money because the universe is trying to teach you better money management. It could be that you didn’t get into your desired school because you need to discover your true purpose.

There is a lesson in almost every disappointment. For example, I interpreted my numerous job rejections as an avenue to improve my interviewing and networking skills. I had gotten my past four roles without applying for them. So while I was knowledgeable on the different skills to land a job (e.g., resume writing and interviewing), I had not put any of them into practice in a long time. These skills suffered as a result, thereby reducing my success chances. If I hadn’t gotten at least 60 rejections, I probably wouldn’t come across helpful resources like Uncultivated Culture or this list of contacts that expanded my network.

4. Learn from your mistakes

You might be your most giant opp. Yes, you’ve had over 200 job rejections. But what if these were due to your poor interviewing skills? Or worse, you can’t write a proper resume to save your life. What if the inability to nurture relationships is the cause of your stagnancy at work?

In my situation, my termination would probably not have happened if I had handled a one-time clash with my marketing manager gracefully. Accordingly, I’m improving my conflict resolution and teamwork skills.

Just as I’m acknowledging my contribution to my losses and the need to grow, you should learn from your failures too. Don’t just cry about your problems. Get your act together so it doesn’t repeat itself.

5. Talk to people

It’s easy for you to think your obstacle is the biggest ever faced in the human race. Fortunately, when you speak to other people, you realize you’re not alone. Even better, you release pent-up feelings and break from negative patterns you might not see on your own. So please, vent. Don’t isolate yourself at rock bottom. If you can afford a therapist, great for you. And if you can’t, find solace in the safe spaces created by your friends and loved ones. If push comes to shove, rant to strangers.

The more you learn we are all in this together, the more you’re able to weather through your storm victoriously.

6. Live and love

Capitalism deludes us into thinking our fulfilment lies in the acquisition of material possession. This deception makes us pursue success so much we lose sight of what actually fills our void — connection with others. We become too busy to make time for our family and friends. Work hours seem never to be enough to crush our goals, while time with our loved ones feels long and unproductive. When we eventually hit rock bottom, there is no anchor to hold on to except past accomplishments that left us feeling empty for something. If this sounds like you, you can turn things around by starting to live more.

Go out more. Call your loved ones. Enjoy your creative hobbies even if the corporate world deems them as unproductive. Start a gratitude journal where you record at least ten things you’re grateful for and look at it every morning.

An instance of me living

Above all, nurture and maintain a healthy, loving relationship with other people. George Vaillant, psychologist and principal investigator of a 75-year study that monitored Harvard graduates (from 1939 to 1944) into their 90s, best described happiness: “Happiness is love. Full stop.”

7. Capitalize on the little wins

Winning feels so good because it triggers the release of dopamine (a chemical responsible for pleasure). Because we yearn for this good feeling, most of us set lofty goals. We believe the bigger the goals, the better we will feel about ourselves. Soon, we begin to focus on results more than we do processes. We hope that a big tech job or a 10x increase in our salary will end our unhappiness while disregarding the little steps to accomplishing these big goals, e.g., upskilling and reaching out to at least one person in our dream company daily.

Paradoxically, those little steps matter as much as the huge feats. Bigger isn’t necessarily better. In fact, both big and small wins have the same effect. Goals are simply a yardstick for measuring our progress. It doesn’t matter if this progress entails achieving your to-do list for the day or securing a promotion. Progress is progress. The Harvard Business Review team confirmed this when they conducted a survey that revealed that some participants had their best moments whenever any progressive work occurred in their team. The progress size didn’t matter.

Your little wins sustain your motivation and eventually add up to the significant accomplishments you desire. Make an effort to track your progress and celebrate yourself every day. Whenever you feel down, look back to this track record and remember how far you’ve come.

8. Don’t look at others’ journeys through the lens of envy

Whenever you are at rock bottom, it always looks like everyone else is living their dreams. You begin to see more success stories on your social media feed. You start to see others manifest your desires. Before rushing to envy these people’s wins, I’ll recommend you consider the entire picture of their lives. When you get behind the scenes, can you handle their skeletons? At this point, I’m not so sure you wish to be like them anymore.

So instead of wishing you had their wins, learn from them. If someone gets a job at your dream company or achieves your income goal, study their trajectory. If you can, get on a coffee chat with them to learn what aspect of their strategy you can implement. Don’t be green with envy — glee with inspiration.

Final words

It’d be hypocritical to say I don’t know how heartbreaking this year might have been for you. And while I want to tell you that it gets better, know that you’ll experience more of these low moments in the future. You’ll still go through more periods where you don’t get your desired results, no matter how hard you work. It would seem as if the universe no longer rewards diligence. Success would appear to detest you to the point where it seems it wants nothing to do with you. In the unfolding of these, you’ll cry, stomp your feet, and sometimes lick your wounds.

No matter what happens, realize that none of your negative experiences makes you a failure. Yes, the big wins are attractive. But the small victories matter too.

So while in your dry spell, give yourself the kindness and love you would extend to a good friend in trying times. Celebrate whenever you get to enjoy your hobbies. Appreciate yourself whenever you excel at even the simplest tasks on your to-do list. Rejoice whenever you’re able to pay your bills with the rewards of your hard work.

Life is like a blockbuster with unexpected twists and turns. These Ts exist to advance the storyline of your life — help you grow, learn, and contribute better. So, make a great actor in this blockbuster. Perform flawlessly with the many gifts you have to offer.

You’ll get through this just as a diamond passes through its mining successfully. I’m rooting for you!

--

--