37 Life + Business lessons

Hey, it’s my 37th birthday today, and I thought it might be fun to share some of the lessons and takeaways that I’ve learned over the years. These lessons are a mix of life, business, health, and relationships.

Discernment is a core/essential life + business skill. You will be faced with an endless sea of “shoulds”, and your job is to discover which of those make sense for you. Not all business advice works for all business owners. You can and should take what fits, be willing to experiment, and leave the rest. You can learn a lot from coaches and mentors, but at the end of the day, no one knows you and your needs like you do.
Courage is almost always rewarded. I heard someone once say that our potential for success is proportional to our willingness to take risks, and I believe that this is mostly true. I have a very high tolerance for risk, and I believe this has contributed to my success and happiness over the years.
Nobody is paying attention to your stuff as much as you are. It’s more likely that the judgments you fear are coming from your own head, and not someone else’s. Learn how to manage and work with your fear and judgment, and you will be unstoppable.
Communication is one of the most important skills you can nurture. According to Chris Voss, former FBI Hostage Negotiator, How you say something is 5x more important than what you say. Tone matters, the words we choose matters. You can learn to diffuse a tense situation or get buy-in on an idea, or you can escalate a situation and create needless suffering. Learning to become a better communicator (not just in difficult situations) is a leadership skill that will always be worth learning.
Learn how to have Difficult Conversations. Conflict is inevitable. We are going to face challenging situations throughout our lives. Don’t avoid these difficult situations; they have so much to teach you about yourself and others. Be willing to admit when you were wrong, and be willing to see that there are more than 2 sides to a story.
Making others feel heard is a superpower. Pay attention to your ratio of speaking versus listening. Do you tend to dominate the conversation? Are you actively listening to other people when they speak, or are you waiting to talk? Active listening is a gift. It’s also a skill that can make you the most interesting person in the room.
Learn how to manage your money. If you fear money, if you are uncomfortable talking about it or asking for it, and if you don’t learn to manage it… guess what? You’ll find it slips through your fingers. Interest compounds, so the sooner you learn how to manage your money, you will start seeing the compounding interest over time.
Pay yourself first. Adopting the Profit First method of banking + bookkeeping will change the way you see your business. It makes decision making easier, and it makes sure that you understand the profitability of your business. It took me a year from buying the book to implementing it, as it took me some time to wrap my head around, but once I implemented this, it changed everything. I cannot recommend this method enough.
Don’t take anything personally. When people are cruel or rude to you, it’s usually a reflection of their own pain, fear, and insecurity. It truly has nothing to do with you. The sooner you learn to let go and stop feeding the trolls, the better off you’ll be.
You can change your mind. Anytime. Don’t get stuck in decision paralysis because you’re afraid of making the “right” decision. Most of the time, there isn’t a right solution. You can make decisions that are “right for now,” and change course later. Be slow to make permanent decisions.
It’s easy to take your health for granted. Just like a bank account, the daily and weekly deposits we make can have positive or negative compounding effects. Use the 80/20 rule. You know, 20% cheese...
Understand different attachment styles. Your Brain on Love was one of the most useful and interesting resources that I believe set an incredible foundation for my relationship. There are different attachment styles, different emotional processing speeds, and different ways of expressing and receiving love. Understanding these different archetypes will help you understand yourself and your partner in a deeper way.
Don’t assume anything. It’s really easy to project our own lens and experience onto others, but most of the time, you don’t really know what is happening behind the scenes for other people. We don’t know other people’s battles or struggles, we never have all the facts, and we most certainly have our own unconscious biases. Don’t assume you know all the facts, and don’t make up stories. Keep an open mind.
Boundaries are kind and necessary. People-pleasing is a problematic behaviour that inevitably leads to resentment. Learning how to set healthy boundaries will set you up for a lifetime.
We are a product of our families. I didn’t want to believe this for a long time, but we are inevitably shaped by our experiences within our family units. It’s worth digging into what beliefs, patterns, and behaviours you have unconsciously learned, internalized, and normalized. Therapy is one of the most powerful tools for helping understand the patterns and messages that have been imprinted into our subconscious that we may not agree with, or that may not be serving us in our current lives.
You will outgrow friendships and relationships; there’s nothing wrong with this! We are aligned with people at different stages in our lives, and sometimes our lives change dramatically in ways that make it difficult to relate or support one another. Everyone is on a different path to growth. Sometimes friendships survive this growth, sometimes they don’t!
Design from Patterns to Details. Look at the bigger picture before jumping into details or looking at things in silos. There are often larger higher-level behaviours and patterns happening at a system level that influence all the “parts.” Resist the urge to plant new seeds when you don’t know the quality of the soil, or the patterns of the sun.
Get support. It might be tempting to want to do it all yourself, but hiring the right kind of support at the right times in your business will allow you to focus on the areas that are 1000% aligned with your natural strengths and proficiency.
Hiring Coaches and consultants can be a powerful way to fast-track your learning and progress. I have always have at least one coach, ranging from systems coaching, to leadership coaching, speaker coaching, marketing consulting, and more. (Admittedly I did this even when I couldn’t afford to…)
Masterminds will help you level up. I have been participating in masterminds for almost as long as I have been in business, and I believe these groups are a huge part of my own evolution and success as a business owner. Having a place to share wins, struggles, and get support identifying your blind spots is a game-changer.
Don’t do the same work twice. Anytime I have to do something, I ask myself, how else might I use this? Chances are there’s room to re-use that work/wisdom/content in another format. Consider your outputs from the beginning and it may bring more creativity to your approach.
You are not your target audience. Just because you aren’t willing to pay $x for Y, doesn’t mean others aren’t willing to. We tend to massively undervalue the things that come easily to us.
Feed a starving crowd. It’s way easier to build something that people are already asking for, than to try to create demand for something we think people need. If you are listening carefully to the market, people are usually expressing their frustrations and desires everywhere from Twitter, to Amazon reviews, to Facebook groups, and in various online communities.
Sell transformation, not yourself. People often get awkward about “selling,” and I too have struggled with this at many times in my career, but you aren’t “selling yourself,” you’re selling people a better version of themselves. It’s much easier to talk about the transformation you help people create for themselves, then trying to sell yourself as the answer to someones problems.
Not everyone is going to like you or like what you do. Chances are if everyone likes you, you’re not trying very hard. Your work, opinions, and ideas should closely align with some people and not with others. This is normal! Don’t take it personally.
Listen to your “hut” (heart + gut, a la Alexandra Franzen). Most of the times we know when something is off, or what we need to do next, but we’re sometimes scared of the consequences of saying it. Your hut always knows. I believe we pick up on a lot more subconscious information than we realize.
“They may forget what you said – but they will never forget how you made them feel.” This is one of those quotes that is a guiding philosophy for how I live my life. I want to leave people feeling more empowered in their own lives.
Know your purpose. When you know why you do what you do, all other decisions become easier. You can check in to see if projects or decisions are aligned with your purpose. Don’t skip this work. It’s difficult, but it’s worth doing.
Be clear on your values. Similarly, what values guide your behaviour and decision making on a day-to-day basis? When you understand and know your values, you will start to better understand your own behaviour, triggers, patterns, etc.
Make it visible. Vision, Goals, Projects, Commitments, Purpose, Values, Priorities. Make sure that you have these things somewhere easily visible. (This is a huge part of why I love Notion so much – it has helped me make so much of my work visible, which helps anchor decision making and really understand what I’ve committed to).
No is a complete sentence. You can say no to something without having to have a reason why, or giving an explanation. If something simply isn’t a fit, you can say no.
Understand your strengths and weaknesses. Everyone has things that they are naturally good at, and enable them to operate at a high level. Similarly, there are places where you are going to struggle and fall short. Don’t beat yourself up for the things that aren’t your natural strengths. Learn to adapt/cope with weaknesses, and find ways to leverage your strengths. Design your life to allow you to optimize for what keeps you in flow.
Embrace Your quirks. Those weird things that you’ve been criticized for your whole life? The things you think about weird about you? Those are likely part of your superpowers. Don’t fight your weird edges; they will make you stand out.
Writing is one of those skills that will always be valuable. It’s worth learning how to write well; writing will help you communicate your ideas with others. Similarly, good copywriting can be the deciding factor between two similar products. Better copywriting wins every time.
Starting is the hardest part. We build up so much fear, and so many stories that we’re afraid to put our work out there. And yet we feel disappointed for not having the results we want. It’s a bizarre cycle where we’re disappointed in our lack of results, but we also haven’t yet done the work that gets the results. Most of the time, our minds are the only thing preventing us from taking the next step.
Emotions aren’t bad. Emotions have a function. They are there to signal something to us. Anger is not “bad,” it’s a signal that a boundary has been violated. “Anger tells us that our boundaries have been violated. Much like a nation’s radar defence system, angry feelings serve as an “early warning system,” telling us we’re in danger of being injured or controlled.” – Boundaries
Reviews are a life-changing habit. When you pay attention to where your attention is going, you can course-correct and identify challenges in advance. What patterns keep emerging? What do you want to change? What is working well, and what is challenging you? You can design your life and business to add friction where you want to reduce certain behaviours, and reduce friction where you want to incentivize good behaviours. Daily journaling, weekly reviews, and monthly reviews will help you reach your goals faster.