⚡️ Today’s level up ⚡️
It’s the third week of January, and before we get too wrapped up in the chaotic activities of being a performance-based professional, let’s take a step back and get real. Today’s story and system is about peeling back the complicated mental and emotional layers that come with our roles. I’ll share my battles with mental health and provide 5 actionable ways you can systemize success and satisfaction in your life.
Read time: <7 minutes
The mental game is hard
I was triggered recently watching the Netflix documentary “Untold: Breaking Point.”
I was reminded of some dark moments in my life.
As a 20-year-old athlete trying to win a pro contract in Europe, I remembered:
→ The hiding
→ The extreme anxiety
→ The obsessive thoughts
→ The dangerous, defeating self-talk
→ The eating disorder (yes, men get them too)
Perhaps I had suppressed these feelings for a long time and they bubbled up as I watched Mardy Fish (a former #1 ranked men’s US tennis player) document his own mental health battles.
It was a mirror on some of the internal battles I suffered with.
Things I thought were normal at the time.
I had to “just toughen up” and “deal with it” I told myself (and society tells men).
If I didn’t become a pro, “I was worthless.”
“I might as well not exist.”
I didn’t win the pro soccer contract, but I could’ve easily won an Oscar, because I became a damn good actor.
Some people around me probably thought I was a dick because I portrayed this super confident, “I can do anything,” external persona.
I may have even been so good, that I convinced myself I was okay.
But the truth was, I wasn’t.
Pressure doesn’t only come from outside factors
To be clear, these were high stakes I put on myself.
It wasn’t pressure from the outside. It wasn’t like I had demanding parents pushing me to the limits. I was supported, and people around me just wanted me to be happy.
But my thoughts of happiness were so heavily tied to an impossible outcome. And that’s a dangerous place for one’s internal self-esteem and well-being.
Of course, it’ll be a longer journey to unpack the things that drove me to this highly obsessive state in the first place. But that’s what therapy is for.
Luckily, things worked out the way they did and my obsessive over-training caused me to develop a career-ending overuse injury.
That started an interesting, highly introspective journey into writing, meditation, yoga, and Buddhism. Slowly, I peeled back some of the complicated layers of my onion.
Fast-forward to entering the demanding role of sales, and I started to confront some of the pressures and broken processes placed on performance-based professionals.
These feelings of tying my self worth to performance came back.
I had learned some effective coping and processing tools, but like a shark, when you get a taste of blood in the water, watch out!
Transitioning to sales
As I entered my first sales role in 2006, I was reminded of some of those internal pressures to succeed, especially when they are exacerbated by outside pressures.
As time went on, so did my progress in sales. I learned both good things and bad things.
The bad things being a “work around the clock” mentality to meet your targets attitude. That put me in some trouble, physically, mentally, and emotionally…including a trip to the hospital in 2011.
I didn’t quite learn my lessons, but once I was stalling my earnings (leave it to money to be a motivator for a seller), mixed with the feelings of constant burnout, I knew things had to change.
That’s when I got to work on redesigning a new approach to my craft – one that looked for different ways of measuring my success and satisfaction. Here were the 5 things that were extremely beneficial to me.
1. Get help
Gaining an outside perspective is very beneficial – from therapy, to mentoring, to coaching (or all of the above).
These will be investments that are well worth the money, time, energy, and attention.
Once I starting working with mentors and coaches in 2019, not only did I 7.5x my income, I became more strategic in how I got there by not focusing on money, but pursuing work that fulfilled me – that up-leveled my life in every way.
2. Deploy the “3 Level Rule”
→ Level 1: Find people you trust and respect 3 years above you
These should be people you admire and want to replicate the path they’ve taken. You’ll benefit from their specific knowledge and systems, as well as avoid their mistakes.
→ Level 2: Find people you trust and respect at your current level
These should be your peers and support network. You’ll benefit from sharing knowledge, experimenting with new systems, and supporting one another when things get tough.
→ Level 3: Find people you trust and respect 3 years behind you
These should be your younger colleagues and mentees. Both sides benefit from your coaching and mentoring – you solidify your knowledge and they get lifted up.
3. Understand your capacity
The most prolific time in my career from 2020 – 2022 was also when I was working the most intentionally.
I didn’t step foot on a plane once to meet a client, yet I was closing 7 and 8 figure deals while averaging 7 hours of sleep each night.
Instead of focusing on activity, I applied my efforts on areas where I could make the most impact. And in order to make the biggest impact, I needed to be the best version of myself.
But this habit tracker wasn’t based on how many calls I made or how many proposals I sent every month. No, it was trying to understand my capacity – how many meetings could I run each day while having enough time to do the quality deep work for the appropriate strategy from these meetings, all while getting workouts in, time with my wife, feeling in a good mood, and sleeping well.
I encourage you to develop something similar, and adapt it to your own work and life (feel free to steal mine if you need a place to start). Doing this exercise consistently every work day helped me learn a lot about myself, like my highest “Thrive Score” was when I:
→ Did my most important task 90 mins after waking up & before my first meeting
→ Focused on responses at a specific time vs staying in my inboxes all day
→ Spent 25+ mins taking breaks outside throughout the day
→ Participated in no more than 4 hours of meetings in a day
→ Completed 6 concentrated blocks of deep work
→ I planned out the workday the evening before
→ Slept 7+ hours the night before
This will, and should be different for you. I encourage you to experiment to find your own winning recipe.
And once tracking my habits became a habit, just like brushing my teeth or making my morning coffee, it was insightful and enjoyable, not a burden. In fact, I had gotten away from this over the past few months, and once I started using Thrive Space again this month, I noticed my well-being significantly improved.
4. Create anchor moments you don’t break
Put time on your calendar for the “anchor moments” that give you the opportunity to work strategically on the things that matter to YOU.
Think about these moments on a micro, meso, and macro time horizon, like this:
→ Micro: Daily + Weekly
I have a daily “startup” routine and a “shutdown” routine. Why the start and end of the day? These are moments I have more control over, and they help create deliberate moments of warming up so I’m ready for my most important task and shutting down so I can be more present in other areas of my life without work tugging at me.
I also block off 60 – 90 minutes each week for a Weekly Review. This is when I check in with myself to ensure I’m moving forward in the direction I want and focus on scheduling and prioritizing my highest value activities.
→ Meso: Monthly + Quarterly
On the first business day of the month or quarter, I take the first half of the day to do my “Wash The Dishes” routine, where I get clean, get clear, get confident, and get inspired.
→ Macro: Semi-Annually + Annually
At the middle of the year and end of the year, this is when I take a full day (preferably in an inspiring location) to check in with myself on my theme and annual plan, as well as make adjustments, updates, and check in on my progress towards my personal North Star.
5. Reframe your role as a seller
If you’re anything like me, you were drawn to sales because of your entrepreneurial spirit. You enjoy the flexibility and autonomy but also the challenge to solve big problems and help others.
A useful reframe in the latter years of my sales career was thinking of my role as way to fund the next stages of my life. I lived (happily) off of my base salary and used the rest to invest in myself. I was like a brand and VC as one.
Knowing your role has more meaning, whether that’s to free up more time with your family one day or to help your clients in the most impactful way possible, will help you to keep things in perspective and stay focused on what’s important and not the short-term tactics that may burn bridges (or burn you out).
Improve your mental game with 3 trusted resources
Knowing you don’t have to figure things out on your own can be the biggest lever you pull, and can set the stage for performing at your best without burning yourself out.
I have partnered with 3 people I believe in deeply and want to share these awesome resources to the community.
→ Amber Deibert. Amber was the mindset coached I worked with back in 2019 on my path to my highest earning year. She specializes in helping enterprise AEs sharpen their mindset and overcome imposter syndrome. Book a session with Amber.
→ Jeff Riseley. Jeff provides mental health and resilience training for sales teams, leaders, and individuals. His course uses a science-backed approach to help sellers maximize mental performance in sales. Download Stress Less, Sell More.
→ Tim Perreira. Tim and I worked together at a late stage startup in San Francisco. Tim has gone on to leave sales and has been working with men to help them get unstuck, find purpose, and build healthy habits that stick. Join Tim’s The Academy Program.
See you next time!
When you’re ready, here are 3 ways I can help you:
This combines the 7 Steps to 7 Figures system along with lifetime membership to our Make More Hustle Less Club where we put the system in action as a community.
You can book a 60 minute session with me here (however you save more if you do option 1 and bundle in a strategy call)
All Q1 slots are filled, but I will be selecting Q2 spots in about 6 weeks.