The 35 Lessons That Shaped My Year

I recently sat down to reflect on what I learnt from 2018 — a year that saw me grow more as a person than ever before. Inspired by a piece from Sam Altman, I decided to write my lessons out in bullet points so I can revisit them periodically and ensure I continually work on implementing them into my daily life. Some of these I learnt from others, some through doing, but each has had a profound impact on me.

Although some of my lessons were bespoke to start-ups (which I will save for another article), these are the 35 that I felt could apply to anything that I do. I wrote this piece for my own personal benefit, but I hope that by sharing it others can benefit from these too. If you resonate with what I’ve written or have a different perspective on any of the lessons, feel free to reach out in the comments below. I love the conversations that follow :)

On Goals and Ambitions:

2. Don’t judge others, help them: When someone shares their plans and dreams with you, don’t judge them or hope that they fail. See how you can help or, at the very least, genuinely wish them well. We can all be tall poppies together.

3. Don’t aspire to be one person: There are likely too many factors out of your control that will inhibit your ability to live that person’s life. Instead, consider the qualities in them that you admire and aspire to have those.

4. Work on something you’re truly passionate about: Being passionate about the type of work you do is great, but being passionate about the subject of your work is even better. It’s a beautiful thing when you see someone who has married these two things together.

5. Ask for what you want: Often it’s best to be direct with what you want. If you can’t get it, uncover why not and work on bridging that gap. You won’t know what that delta is until you ask.

6. Take risks: Life is too short to be left wondering “what if?”. Most people are conservative by nature so the advice you receive will be biased to be risk averse. Apply a regret mitigation framework to significant decisions in your life to give yourself the best chance of fulfilment.

7. Do something bold that challenges yourself: Stretch your limits by putting yourself outside of your comfort zone personally and professionally. Surround yourself by people who have mastered that challenge before and you’ll have a much higher chance of success.

On Mental Wellbeing:

9. Invest in your own mental/personal development: We aim to be the top 1% of the top 1% in our industries and yet most of us heavily underinvest in our own development. Professional athletes are surrounded by coaches and support staff to help them succeed and we should be no different. Invest in a well-vetted professional/executive coach and you’ll see your development accelerate dramatically.

10. Don’t overbook your calendar: Work is like sleep, the more interrupted you are during it the worse the end-result will be. Schedule blocks of time (usually mornings) where you consistently don’t allow any meetings to be booked and guard this time for deep work.

11. Allow people to be in an environment where they operate best: You don’t have to prove to others that you work longer/harder than they do; let your results speak for themselves. With advancements in technology, working remotely is more possible than ever and can lead to increased productivity and happiness for you and your team. Aiming to be first in and last to leave is an antiquated mindset.

12. Limit your time on social media: As with most things, social media usage can be good in moderation. However, social posts are inherently skewed to reflect only the positive experiences of our lives. Particularly in challenging times, this can have a negative effect as you contrast your total pool of experiences with only the positive ones of others. Be aware of this, and consciously try avoid it by removing easy access through native apps etc.

13. Make time for nature and hobbies: Have a day off a week where you do something purely for the enjoyment of it. This can easily slip by the wayside but you’ll find that you get to the end of the year and all you’ve done is work. Personally, I find working 6 days a week is optimal but 7 is unsustainable.

14. Don’t accept responsibility for other people’s actions: People are unpredictable and often don’t act rationally. You aren’t responsible for anyone’s actions other than your own.

On Learning:

16. Curiosity often beats experience: The greatest people to work with are those that are inherently curious. Weight this more heavily in hiring decisions than an impressive resume. Reading books and listening to podcasts can be a good indicator of a curious mind as it gives an insight into how someone utilises their personal time.

17. It’s okay to fail, thrive off the learnings that come from this: Not everything goes the way we planned. If you fail at something, seek to learn as much from that experience as possible so you are better prepared for it the next time round.

18. Go out of your way to seek feedback from people: Feedback can be daunting at first but if you learn to love it, it can be the fastest way to grow. Proactively seeking feedback from your peers will also mean you’re in a better mindset to receive and action upon it.

19. Be comfortable with the unknown: People won’t always be able to move at the pace that you would like them to. Although not being able to reach an answer or construct a plan immediately may feel uncomfortable, being able to sit with the unknown can avoid you taking a suboptimal path just to get through the ambiguity.

20. Be interesting: Go deep on a new skill or subject area each quarter. Whether it’s consuming a bunch of content on a topic you’re interested in or learning a new design tool, an instrument, a language etc. keep expanding the boundaries of what you know.

On Values:

22. Don’t concern yourself with what others will think of your actions: As the stakes get higher, it can become increasingly harder to appease all parties. This is when it becomes even more important to always act within your values set. It takes courage to do this, but if you’re guided by fear of being judged by others you will lose your way very quickly.

23. If it doesn’t feel right, don’t do it: There is a difference between taking a calculated risk and doing something that your gut is intrinsically telling you not to do. Whether it’s hiring a new staff member, sending a text/email, or making a big strategic decision, if something feels off take the time to journal about it and this will help you rationalise the correct path forward.

On Responding to Others:

25. You almost always have a choice: Even when you feel pressured by others to respond. Sometimes saying nothing is the best approach; you don’t have to answer every question that is asked of you.

26. It’s okay not to know something: Be honest about it and then find the answer. People will respect you more than if you guess and are wrong.

On Money:

On Friendship & Relationships:

29. Be nice to others even when you don’t expect a return: Take pleasure in helping others just for the sake of helping them; you never know when or how this goodwill can repay itself.

30. You can meet the right person at the wrong time: Sometimes factors in life can get in the way of a relationship that feels right. Have the courage to let it go and you’ll have a stronger chance of it succeeding when you’re both ready.

31. A few close friends is better than a hundred acquaintances: Focus on having closer & stronger relationships. Life is not a popularity contest.

32. It’s okay to mix friends with business: Even though I’ve seen this go the other way, I’m still a believer that you can succeed in business with your close friends. If your friendship is damaged through working together, then perhaps the environment just accelerated what already needed to be addressed.

33. Not everyone wants what you do: People are driven by different things in life — it’s wrong to assume that everyone wants what you do. Understanding what these are in others can lead to really healthy relationships.

34. Humans have amazing stories: Most people aren’t used to having someone else take a deep interest in their journey but every life has fascinating twists and turns to share. Take the time to learn the stories of people you meet with and you’ll find you create much stronger connections with them.

On Happiness:

Let’s make 2019 even more memorable!

Chief of Staff @ Skedulo