A mentor once explained the two paths to finding happiness as you get older: the lazy and the painful.
The painful option requires you to endure lots of poor outcomes and to learn from each one. The wisdom you gain from those lessons will position you for a happier second half of life.
If you’re smart, however, you’ll take the lazy path. Instead of experiencing those dreadful outcomes yourself, learn from the mistakes of people who came before you.
Throughout most of my twenties and thirties, I did neither. I never learned from others and never took responsibility for my own failures and poor decisions.
As my dissatisfaction mounted, I eventually faced reality. Little by little, I reflected on life, learning from my experiences, and applying that wisdom to my decision-making.
Today, mere months from turning 50, I’ve never been happier, more productive, and more creative. But my journey could have been less painful. As my mentor once advised, it’s vital to learn from your errors, but it’s better to avoid those mistakes by harnessing the wisdom of those who came before you.
These five lessons will prove most beneficial if you’re still on your journey.
Moments of struggle force you to grow if you embrace the challenge.
In 2005, my business collapsed. My savings had vanished, and I had no source of income. If I had been single, I might have surrendered and moved back in with my parents — that’s what I did seven years earlier in the same situation. But I was in love and refused to give up, so I fought to salvage financial independence.
Instead of playing it safe, I battled for a six-figure job way beyond my qualifications at a company that didn’t even have an opening. To win it, I had to do things I had never done before: ask for help, risk rejection, and harness my nascent powers of persuasion. Somehow, it worked out, capping the wildest six months of my life.
What it teaches you
When you face adversity, don’t seek survival; aim to thrive. Misfortune will sap your will if you let it. But fighting your way through it forces you to do things beyond your capability; that’s how you grow and expand your comfort zone.
When the tension ends, you’ll look back on your struggle and recognize it as one of your most rewarding life experiences.
Money won’t make you happy, but you won’t believe it until you experience it.
In one of my first jobs, I worked for a large hotel in New York City. The 70-hour workweeks drained me. The puny salary failed to compensate, and my distaste for the work bankrupted my soul. What sustained me were the mini-promotions they gave every six to twelve months.
Whenever I’d get one of those promotions, I’d feel validated. A few weeks later, I’d come down from the high and feel miserable again. By the end of my tenure, I had become mentally and physically exhausted.
Still, I failed to learn my lesson. I moved to another career for one reason only. It paid better than any other one. It wasn’t until my forties that I concluded what others had advised. You can’t sustain success doing work that doesn’t fulfill you.
What it teaches you
Money needs to be a byproduct of the process. By itself, it won’t make you happy. You know this intellectually, but it’s hard to internalize until you’ve experienced the burnout and the disillusionment of living a dream that isn’t yours.
That’s the abstract, but it’s not always reality.
Quitting your day job to do something you love is unrealistic for most people. Instead, dedicate an hour a day to working on something you’re passionate about. It’ll make your day job a bit more bearable. In time, you may be able to make a full-time living doing what you love.
Shortcuts never pay off, but commitments do.
It’s embarrassing to admit, but for much of my life, I looked for shortcuts. From business to relationship success, I sought every shortcut scheme imaginable: get rich quick, find love fast, become a genius overnight. They never worked.
Shortcuts don’t quicken the time to reach your goal; they waste your time on fruitless activities. Few people escape adulthood without falling prey to one of these quixotic fantasies; they’re too enticing.
What it teaches you
At the age of 44, I finally learned my lesson. That’s when I recommitted to being a writer, not merely giving it a shot but committing for the next 25 years.
It might sound like a long time, but no rule says you have to stick it out for that long. It’s the mindset that matters. If you’re in a rush to hit goals, you’ll opt for get-rich schemes and the like. With a 25-year timeframe, you focus on consistency and getting a tiny bit better each day. In my 49 years, it’s the only path that’s ever worked for me.
If you find success or love, you can thank luck.
I write a lot about the lessons learned from my many failed relationships and my lone successful one. Truth. I often leave out an inconvenient fact. My successful one had a lot to do with luck, genuine luck.
My future wife was eight weeks away from moving out west. I’d given up on any chance we’d ever date.
The night we got together for the first time, I was at my parents’ house and left early to catch a train back to the city with the hope of popping in to see her at the bar she’d be at — one last shot.
The doors to the train were about to close as I snuck inside. Luck.
Two hours later, I returned to my apartment and sent a quick text to see if she was still at the bar. My text caught her minutes before she left. Luck.
Later, I learned she had gone there to meet another guy who never showed. Luck.
If any of those three events didn’t happen, I might still be single.
What it teaches you
Everything was set in motion by my decision to give it one last shot. So many times in life before that, I had given up too early.
When you feel like saying no, say yes. Keep taking one more shot and give luck a target to hit.
When you find happiness or achieve success, it’s not solely because you’re an awesome human being who battled demons and slain dragons. There’s almost always a bit of random chance involved. By putting yourself out there and experiencing more instead of less, you increase the statistical probability of letting luck find you.
To Really Love Yourself, Embrace Being Alone.
I spent most of my twenties alone. For one five year stretch, I hadn’t gone on a date with the same woman more than once. As friends settled into relationships, I became envious and desperate, so I decided to couple up with anyone who wanted me no matter my feelings.
In the beginning, I convinced myself it felt right, but eventually, reality caught up with me.
For the next two years, I embraced being single and experienced more happiness than at any other time of my life. It was the phase where I finally learned to love myself. My self-confidence grew, and that made me more appealing when the right woman came along.
What it teaches you
In my twenties, I wasn’t ready for a relationship. I needed to work on myself first, but I couldn’t do that until I embraced being alone.
Give yourself two years to not care about being in a relationship. Free up that brain space and use that time to get to know yourself and enjoy life. As you become more comfortable with who you are, your self-confidence grows, and that makes for a happier existence, whether the right partner comes along or not.
All you need to know
- Struggles can be a springboard to growth or a trap-door to surrender.
- You might take a job you don’t like because you need the money. There’s no shame in that. But dedicate one hour per day to your passion.
- Avoid shortcuts. Consider the 25-year commitment.
- When you feel like giving up, take one more shot. Luck favors those who play statistics.
- Get comfortable with being alone.