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⚡️ Today’s level up ⚡️

Today’s edition helps you implement a simple framework to upgrade your mindset based on where you are in your career.

Let’s go!

Read time: <7 minutes

My journey in (and then out of sales)

I did not start my career in SaaS (Software-as-a-Service) sales.

Back in 2003, after leaving college early (yep – no bachelor’s degree), I started training youth soccer players. At that time, I was an aspiring professional soccer player. Once I realized I was not going to make it as a pro player, I decided to train younger players instead.

I began working at a company called Coastal Soccer. The trainers were former American collegiate and professional players, and together we came up with a unique training method.

Our core niche was training 5-12-year-olds across Long Island in New York (which gave me a great business education in “niching down” and “Category Design,” which are red hot topics these days).

That first job also gave me a gift I wasn’t expecting – learning how to sell:

And the best way to sell is to stop selling.

Within four years, Coastal Soccer grew from a company of four employees to over fifty. I wore many hats, but was mostly in charge of scaling our individual and small-group player development division.

I eventually left that company so I could work and live in NYC. I even taught myself to DJ to supplement my income and (barely) pay my rent.

My first actual sales role was as an Account Manager for a boutique music marketing agency, which launched my dedicated career in sales in 2006.

After leaving NYC and starting all over again in a small town in Florida – I began to “adult.”

I got married, began getting serious about my sales career (starting over at the bottom in SMB sales), and bought our first house.

Gradually I parlayed my network and experience into moving into SaaS within the region (still focused on SMBs), and then eventually grew into Mid-Market sales at a consulting firm, until I landed a remote Enterprise AE role in 2015, and then finally switched to a remote strategic accounts role in 2018 that launched the most prolific period in my sales career ($50M TCV closed in <4 years).

Then in March of 2022, I said goodbye to corporate selling for good to launch my one-person business.

It was not always easy

Like many in sales, particularly SaaS sales, I had to constantly hustle to stay relevant.

Here was my typical routine:

I would get up early because I was told successful people had to be up by 5 am.

“You need to get a jump on the competition,” I thought to myself.

Then, I’d work frantically, all day, mostly inside my email inbox. I’d be hyper-responsive to any incoming request from any prospect. I’d type furiously away on Google Chat and Slack to my countless co-workers, ensuring presentations, demos, Infosec audits, and contracts were all moving forward.

Then, around 2 pm, when my eyelids were getting heavy, instead of taking a break, I’d run to Starbucks for a quad shot latte or grab a Red Bull (at least it was the sugar-free kind).

Late into the night, I’d continue responding to emails, and tweak a slide deck for my presentation the following morning, all while constantly traveling for meetings with prospects or attending events.

Success came.

I won the deals, surpassed my quota, and then did it all over again, month after month, quarter after quarter, and year after year.

But…it was a vicious and exhausting cycle.

It got so bad, that at one point, in my early 30s, I had a mini-stroke.

All because I had prioritized work over my health.

So what changed?

How my mindset shifted throughout my journey

I became more intentional with how I approached harmonizing work, life, and play – something I describe as the path of The Purposeful Performer.

I’ll unpack this concept in more detail in future editions (in fact, I have a lot of exciting announcements coming this summer), but as a simple visual, it looks something like this:

The one consistent controllable I had throughout each stage (which you do too), was my mindset.

Here’s a breakdown of each stage and how I upgraded my mindset…

STAGE 01: LEARNER

• Objective: Apply effort to learn key skills
• Stage of Career: First decade, earning <$200K
• Mindset: Thought like an Executive

As an individual contributor, I wanted to think more like how an executive does.

✔️ Be super strategic with my decisions

✔️ Understand business implications at a high level

✔️ Remove frivolous distractions (like corporate gossip & politics)

‣‣ Outcome: Gained key business skills (that my peers lacked)

STAGE 02: EARNER

• Objective: Leverage skills to earn outsized income
• Stage of Career: Second decade, earning >$200K
• Mindset: Thought like a CEO

As a top biller and earner, I wanted to think more like a startup founder.

✔️ Say no more than yes

✔️ Develop systems to scale my impact

✔️ Focus on only the most important projects

‣‣ Outcome: Turned my skills into outsized income & autonomy (that my peers didn’t get)

STAGE 03: CREATOR

• Objective: Turn life-changing income into freedom
• Stage of Career: For the rest of my life
• Mindset: Think like a VC

As a financially-independent solopreneur, I want to make decisions based on creating independence and impact.

✔️ Build a calm business

✔️ Sustain long-term thinking

✔️ Diversify my income streams

‣‣ Outcome: Designed a business around my life (vs the other way around).

Hope this helped put some things into perspective on your own journey.

See you next week!

When you’re ready, here are 3 ways I can help you:

1 | Unlock the 7 Figure Seller OS

Most readers have opted for the Intermediate Program, which combines the 7 Steps to 7 Figures system along with a membership to Make More Hustle Less Club where we put the system in action as a community and members have access to over 14 hours of available on-demand content.

2 | Book a 1:1 coaching session right now

You can book a 60-minute strategy session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount (just 8% of available coaching slots remain for 2023).

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