Credit: Ben White

I agree with Gary Vee — Why your happiness starts with self-awareness, not a preoccupation with peer parity

I’m writing this fresh from a conversation I had this morning with Gary Vaynerchuk about 2 topics of acute importance to me, both of which he always covers very powerfully: legacy, and self awareness.

As an entrepreneurial strategy, Gary Vee talks about reverse-engineering consumer behaviour so as to intuitively understand what that means for customer context in the future. From that, we can make calculated bets on what products and business models will add value for those customers. The target here is to understand what is coming down the line a few years ahead of its arrival. What does that give you if your intuition is validated? An unfair advantage.

The last 8 or 10 years of my life have been framed by a personal pursuit of happiness. In part, a focus on understanding and validating what are the levers that drive my own happiness, but on a more macro level, what is success for me in the context of my life as a whole? What I’m focusing on is reverse-engineering my own personal and professional behaviours by a brutally honest understanding of what constitutes a successful end-game in my own life. Assuming I can do this effectively, what does that mean in terms of its impact on gaining genuine and sustainable happiness? Again, it’s an unfair advantage.

Over time, and a period of experimentation, validation and continual self-assessment, I feel like I’ve got this figured out. I’m no wealthier or objectively successful than I was before, but I’m infinitely happier and more focused. And that’s because I’ve positioned my goals, behaviours and projects to be as aligned as possible with the fundamental, inescapable and unchanging drivers of my own happiness.


At the start of my career, I was doing something that I didn’t enjoy and didn’t gain any fulfilment or gratification from. I know many others in the same position. Even with a fantastic life outside of work, I was continually dispirited and stifled by my professional dissatisfaction.

I don’t believe that you can separate personal and professional happiness; the two are intrinsically linked and dependent on each other. I don’t believe that I was unusual; an unacceptably large number of people face the same disillusionment. And since I don’t believe that you can separate personal and professional happiness, what that means is that an unacceptably large number of people are destined to see their personal happiness continually stifled, and ultimately unfulfilled by their professional sadness.

This is a travesty.

I firmly believe that happiness is our raison d’être — it’s the most important thing worth aspiring to. So over time I created a professional life that supports and guarantees the fundamental, inescapable drivers of my happiness, which in my case are family and legacy. Everything else flows from these two things.

Becoming increasingly self aware of these drivers has been instrumental in increasing my own happiness.

Family and legacy. That’s it. Family is pretty easy to understand, legacy perhaps a little more difficult. I’m not interested in a legacy comprised of public acclaim, but rather at looking at this from a personal standpoint. I want a legacy that when I assess and evaluate it myself, I could look myself in the eye, so to speak, and be proud of what I’ve done. I don’t need public recognition for the portfolio of things I do over the next 10, 20, 40 and 80 years — but I do want them to be impactful, and for other people to feel and appreciate that impact. Once I got clarity on that, my approach to professional and personal projects evolved overnight, as did my sense of autonomy and freedom.


Given the professional route I’ve taken (short summary — corporate law to venture building), I’m often approached by people looking for help with making similar career transitions. Primarily, I hear from people who are struggling to understand their options, to identify a viable pathway, to upskill in the areas that they consider to be necessary for the path that they aspire to, and to understand how to go about figuring out what those areas are. I love to have these conversations because I genuinely care about assisting and impacting with their development and transition. Why? Because contributing in a small way to increasing net professional fulfilment will form part of my legacy.

In my experience, a successful transition is always underpinned by self-awareness. So when I work with people, that is always the starting point. It’s the single biggest skill that’s required to start moving towards whatever your end goal happens to be — ie. whatever success looks like to you. Particularly in the context of career transition, it’s crucial to be completely cognisant of what drives you, what you can do (rather than what you can’t), and what are your non-negotiables in terms of professional circumstance.

For some people, that’s salary — for others, it’s the mission. For many, it’s prestige and the perception of others. There’s no right or wrong answer here, the only way is to approach it honestly. Mission or impact may be more romantic, but if that’s not how you’re wired then ignoring the reality won’t make you truly happy. The key is to understand what drives you, and to work within that framework — you gain nothing by being idealistic about it.

My personal non-negotiables are autonomy and meritocracy. There are plenty of other things that I’d also like to have, but if they don’t exist I can work around them. These are the rails that support my pursuit of legacy. But if you had asked me the question 5 or 6 years ago, you would have got a different answer. If you had asked me 3 years ago, you may have got a different answer again. For the last few years I’ve had this figured out and over time, increasingly validated. Now, I don’t believe these things will change.


But where I sometimes struggle when working with others, is in breaking through to a brutally honest assessment of their own drivers of happiness. This is self-awareness in action, and when you fail here you set yourself up to fail in the future. Understanding yourself is the first step. And doubtless you won’t get it right first time. But It’s like building a business: by continually hypothesising, experimenting and honestly validating, you will start to edge closer to the fundamental, personal things that drive your happiness. In the parlance of business building, that’s your product-market fit. But if you’re not able to effectively self-assess, it’s catastrophic. And sometimes you can lead a horse to water, but you can’t force it to drink.

All of this is acutely personal, and it has to be. The chase for personal happiness and professional fulfilment cannot be guided by a preoccupation with peer parity. One thing for which I envy Gary Vee is his unflinching absence of concern with what other people think about him. I’m not on his level in this respect, but after recognising the impact this was having, I’m significantly better than I was previously. By realising that I was often being inadvertently guided by this peer parity preoccupation, I have been able to address it, diminish its impact and profit in terms of refining what’s driving me. It’s an illogical sentiment, but incredibly impactful — a feeling that personal happiness would be supported by keeping pace or outperforming your peer-group. It makes no sense, because we know for a fact that what inspires me doesn’t necessarily inspire you, and what engenders my happiness will be different to what triggers yours.

Given that we can only judge ourselves by our own standards, we should define our personal strategic direction based only on our personal drivers. Peer parity is irrelevant. And the starting point to accepting this is self-awareness.

Gary asked me if I’m trying to create a business based on these sentiments, and the honest answer is no. For a long time I thought I was driven by financial gain. I’m not. Then I thought it was professional acclaim. It’s not. For me, it’s about using what I have to improve the status quo, whether for something or for someone else. The size of this differential will be my legacy. And if I have legacy, I’m half-way there. To paraphrase Gary, I can leave the money on the table for this one.

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