Success Advice
My Mentor And Boss Shocks Me By Quitting – How To Be An Inspirational Leader
I had a last minute meeting appear in my diary late last Wednesday titled “Team Announcement.”
Something told me that in a few hours everything was going to change. I was right.
It’s been two years now working in what I would describe as a dream team.
We’re all crazy intrapreneurs in my team and we think outside the box. We challenge each other to go even further. We disrupt the traditional business models because that’s all we know how to do.
To some we are crazy: to all of us, we want to do something meaningful.
Who is my departing mentor and boss?
In one word, “Gandhi.”
He’s a Buddhist guy with a Yoda philosophy on life. Each day he says something out there and it takes me days to figure out what he means. There is no straight answer because everything has a meaning when it comes from him. The meaning often takes a while to figure out though.
Each day, in our team at work, it’s like preparing for the ancient Japanese Battle of Sekigahara. Every day we have strategy sessions to work out how to take down our enemy. When we get dealt a major blow we know it’s only one of the many battles we face. Overall, we’re optimists led by the chief of the army – my boss and mentor.
His departing gift to me
The challenging thing for my former boss is that he loves to give gifts, yet he knows I don’t like material things. Then, one morning on the train, shortly after the announcement, I get a message on LinkedIn from him. The message read:
“…this is my gift to you.”
My foes will become nothing.
My friends will become nothing.
I, too, will become nothing.
Likewise, all will become nothing.
Just like a dream experience,
Whatever things I enjoy
Will become a memory.
Whatever has passed will not be seen again.
With those eight lines of wisdom, my life and career were set to change. He was giving me a message. He knew me better than most and he knew how much this was the best gift he could give. I then saw him at work later and he said:
“When the student is ready, the teacher will appear.”
He knew deep down that I was upset he was leaving. He knew that I wanted the dream of our team to continue with him at the reigns of the army. What he figured out I needed was the reassurance that the next chapter of my career would soon begin.
He wanted me to know that the next great leader would appear when I (the student) was ready. Just as he had come into my life when I was ready, so too would the next boss and mentor.
While having a chapter in your life and career come to a close is hard, it’s exciting at the same time. I’ve learned that uncertainty about what’s next is the beginning of the next massive opportunity. Nothing stays the same forever although I sometimes wish secretly that it would.
All you can do in these moments of your career is be grateful. The last two years have been the happiest time of my time in any business.
Here are the lessons my boss and mentor taught me:
1. Inspired people change the world
My boss never tried to tell me how to do anything. He always led every conversation with inspiration to do something great. He didn’t want us to be mediocre and be like everyone else. The fact we were a bunch of misfits and didn’t fit in was what he wanted us to embrace. He wanted us to be proud of our unique identity.
Inspirational leaders don’t focus on the how; they focus on the why. Because our team knew why we existed and what our mission was, we always found a way. When our critics laughed at us, we chose to push on. In front of our critics, we always showed respect and smiled. That smile came from a sense that the good guys would win. That good would prevail evil.
Our team was inspired to change the face of our industry. We went after the big stupid goals that everyone said to run a mile from. We put our careers on the line every day. We took calculated risks that others thought were haphazard.
“Nothing, my boss taught us, should ever be done without a why. Everything should have a purpose”
2. Relationships always trump the price paid
Many of the clients we dealt with as a team came about through relationship not price. Each of our clients have become like friends. Doing business with my boss and the team feels like going to a family BBQ. My boss taught us that doing business should be based on trust, your value proposition and the feeling of partnership. Partnerships are based on win-win scenarios.
Both sides in every business interaction should feel like they have won. That’s how you know you’re on to something. That’s the way business should be.
3. Solve real problems
My boss has a fancy job title and with that comes lots of people who want to pitch a product or service. After some meetings, where we saw something cool, my boss would look very pissed off. I’d ask him what was wrong. He says:
“Tim, what problem are they solving? If you’re not solving a problem then you shouldn’t be asking us to buy from you!”
I thought about that often and realized he was spot on. There’s a lot of clever marketing and companies that have raised money from thin air. These companies only make it when they solve a real problem.
Whatever you do in your career, do your best to try and solve a problem. The bigger the problem, the more money you’ll get for solving it.
4. Critical thinking is a rare trait
The one thing that frustrated my boss: lack of critical thinking. Day-to-day in business, we deal with many different characters. Each character forms part of solving a problem (cause that’s what business is after all).
The ability to solve problems effectively, my boss believes, is to use critical thinking. This means that you commit to the following:
– Thinking clearly before deciding on the appropriate action
– Identifying any rational biases beforehand
– Thinking about the connections between different ideas that could form a potential solution
– Being rational about your approach
It’s surprising how rare the superpower is of critical thinking. My boss taught me that it’s something to constantly aim for and to use in business wherever possible.
“Churning out the same old solutions to the same old problems will not move humankind forward. We can all change that”
5. Political capital
Throughout the last two years, it felt like we were facing into a different crisis weekly – such is life. The temptation, my boss taught me, is to try and solve every single one. The challenge with that way of thinking is best summed up through a phrase he drilled into my head like a jackhammer: “Political Capital.”
A lot of business encompasses what you would see day-to-day in politics. Each senior leader is a politician, and every politician only has a certain amount of political capital that they can spend on these weekly crises. My boss taught all of us to spend our political capital wisely.
This political capital over the last two years has been the currency we have used to buy our way into a vision for the future that some may say looked “laughable.” Massive change and seeing things before they happen often involves a lot of critics. The key I’ve learned is to turn these critics into supporters, rather than enemies. As I said before, business is very much like a strategic battle.
6. Customer focus
So many organizations have this concept of customer centricity at the forefront of what they do. It’s not always a reality though. My boss made sure that I understood the importance of making sure the customer was top of mind with every action I took.
I shouldn’t be trying to build anything without having the customer’s input every step of the way. It’s easy to say, but very hard advice to follow. I learned from my boss to do this, or face problems down the road when it’s too late to change.
7. Storytelling futurists matter
Many of our competitors over the last few years were able to win in markets where we were unable to. My boss taught me that the reason our competitors could achieve this goal was because they told better stories than us and spoke about the future.
These competitors spoke about the future and tried to play a part in it. They released products that were way ahead of their time even if they didn’t get the immediate revenue uplift.
Telling stories about the future and releasing products ahead of time gives you a reputation for being a market leader in innovation.
All of us are biased to spend our money with companies who appear to be creating the future we have always dreamt of, even if in reality they are not executing the way it’s perceived they are.
Steve Jobs saw the future of consumer electronics; all of us have the ability to see the future of our industry and play a part in that story.
Stories hold immense power to those who know how to tell them.
Stories make us take action.
Stories inspire us.
8. Your boss can be your best friend
The last two years of my life have been a rollercoaster. Multiple romantic disasters. Huge career wins like going viral all over the Internet. I’ve seen colleagues have major illnesses and even seen crowds of people die right in front of the office I work in.
Through each event, my boss has been there. Like Yoda, he’s always had some words of wisdom that don’t give me the answer but help me find it deep within myself. He’s never given up on me. He’s always inspired me. He’s believed in me and the simple idea that I – just like you – can change the world.
He’s made me see that this life is so short and so is my career.
He’s shown me that everything becomes nothing at some point.
So if everything becomes nothing, then all we have is right now.
I don’t know what the next chapter of my career looks like. I don’t know if I’ll ever have a boss, teacher, or friend like this great man ever again. All each of us has is right now. Enjoy it because change is certain.
So is the way you think about change and the awesome opportunities that come with it. It’s time for me to take a break and have a holiday.
I hope you learned a thing or two about leadership from my boss. I know I certainly did.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
Life
9 Harsh Truths Every Young Man Must Face to Succeed in the Modern World
Before chasing success, every young man needs to face these 9 brutal realities shaping masculinity in the modern world.
Many young men today quietly battle depression, loneliness, and a sense of confusion about who they’re meant to be.
Some blame the lack of deep friendships or romantic relationships. Others feel lost in a digital world that often labels traditional masculinity as “toxic.”
But the truth is this: becoming a man in the modern age takes more than just surviving. It takes resilience, direction, and a willingness to grow even when no one’s watching.
Success doesn’t arrive by accident or luck. It’s built on discipline, sacrifice, and consistency.
Here are 9 harsh truths every young man should know if he wants to thrive, not just survive, in the digital age.
1. Never Use Your Illness as an Excuse
As Dr. Jordan B. Peterson often says, successful people don’t complain; they act.
Your illness, hardship, or struggle shouldn’t define your limits; it should define your motivation. Rest when you must, but always get back up and keep building your dreams. Motivation doesn’t appear magically. It comes after you take action.
Here are five key lessons I’ve learned from Dr. Peterson:
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Learn to write clearly; clarity of thought makes you dangerous.
-
Read quality literature in your free time.
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Nurture a strong relationship with your family.
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Share your ideas publicly; your voice matters.
-
Become a “monster”, powerful, but disciplined enough to control it.
The best leaders and thinkers are grounded. They welcome criticism, adapt quickly, and keep moving forward no matter what.
2. You Can’t Please Everyone And That’s Okay
You don’t need a crowd of people to feel fulfilled. You need a few friends who genuinely accept you for who you are.
If your circle doesn’t bring out your best, it’s okay to walk away. Solitude can be a powerful teacher. It gives you space to understand what you truly want from life. Remember, successful men aren’t people-pleasers; they’re purpose-driven.
3. You Can Control the Process, Not the Outcome
Especially in creative work, writing, business, or content creation, you control effort, not results.
You might publish two articles a day, but you can’t dictate which one will go viral. Focus on mastery, not metrics. Many great writers toiled for years in obscurity before anyone noticed them. Rejection, criticism, and indifference are all part of the path.
The best creators focus on storytelling, not applause.
4. Rejection Is Never Personal
Rejection doesn’t mean you’re unworthy. It simply means your offer, idea, or timing didn’t align.
Every successful person has faced rejection repeatedly. What separates them is persistence and perspective. They see rejection as feedback, not failure. The faster you learn that truth, the faster you’ll grow.
5. Women Value Comfort and Security
Understanding women requires maturity and empathy.
Through books, lectures, and personal growth, I’ve learned that most women desire a man who is grounded, intelligent, confident, emotionally stable, and consistent. Some want humor, others intellect, but nearly all want to feel safe and supported.
Instead of chasing attention, work on self-improvement. Build competence and confidence, and the rest will follow naturally.
6. There’s No Such Thing as Failure, Only Lessons
A powerful lesson from Neuro-Linguistic Programming: failure only exists when you stop trying.
Every mistake brings data. Every setback builds wisdom. The most successful men aren’t fearless. They’ve simply learned to act despite fear.
Be proud of your scars. They’re proof you were brave enough to try.
7. Public Speaking Is an Art Form
Public speaking is one of the most valuable and underrated skills a man can master.
It’s not about perfection; it’s about connection. The best speakers tell stories, inspire confidence, and make people feel seen. They research deeply, speak honestly, and practice relentlessly.
If you can speak well, you can lead, sell, teach, and inspire. Start small, practice at work, in class, or even in front of a mirror, and watch your confidence skyrocket.
8. Teaching Is Leadership in Disguise
Great teachers are not just knowledgeable. They’re brave, compassionate, and disciplined.
Teaching forces you to articulate what you know, and in doing so, you master it at a deeper level. Whether you’re mentoring a peer, leading a team, or sharing insights online, teaching refines your purpose.
Lifelong learners become lifelong leaders.
9. Study Human Nature to Achieve Your Dreams
One of the toughest lessons to accept: most people are self-interested.
That’s not cynicism, it’s human nature. Understanding this helps you navigate relationships, business, and communication more effectively.
Everyone has a darker side, but successful people learn to channel theirs productively into discipline, creativity, and drive.
Psychology isn’t just theory; it’s a toolkit. Learn how people think, act, and decide, and you’ll know how to lead them, influence them, and even understand yourself better.
Final Thoughts
The digital age offers endless opportunities, but only to those who are willing to take responsibility, confront discomfort, and keep improving.
Becoming a man today means embracing the hard truths most avoid.
Because at the end of the day, success isn’t about luck. It’s about who you become when life tests you the most.
Change Your Mindset
Work-Life Balance Isn’t a Myth: Here’s How to Actually Make It Happen
Work stress doesn’t have to win, here’s how to protect your peace and thrive in any workplace.
Starting a new job often comes with excitement and ambition. Yet, beneath that initial enthusiasm, many employees quickly encounter the reality of workplace challenges, especially stress. (more…)
Change Your Mindset
The Four Types of Happiness: Which One Are You Living In?
Most people chase success only to find emptiness, this model reveals why true happiness lies somewhere else.
In a world driven by rapid technological growth and constant competition, many people unknowingly trade joy for achievement. (more…)
Success Advice
11 Mark Manson Lessons That’ll Redefine Success in the Digital Age
Success in the digital age isn’t about hacks, it’s about the raw, real lessons Mark Manson actually lives by.
In 2016, Mark Manson released The Subtle Art of Not Giving a F*ck, a brutally honest, thought-provoking book that redefined self-help for a new generation. (more…)
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