The Journey of Becoming a High Performance Entrepreneur

If you’re someone who, like me, is driven to extract every ounce of your potential in this lifetime, then this blog post is for you. There was a time when I chased fame, fortune, and the extravagant lifestyle that came with it. But life had different plans for me.

Discovering the Illusion

I was all about the Lamborghini Bikini lifestyle, constantly striving to have it all and do it all. I was relentless in my pursuit of external success. However, life threw me a curveball that changed everything. 

An illness left me unable to walk for three long months. As if that weren’t enough, I found myself drowning in a staggering $200,000 debt, on the verge of bankruptcy. It was during this dark period that I had a profound realization.

I came face-to-face with the ephemeral nature of material possessions. The investment properties, my car, and the other “stuff” I amassed disappeared in the blink of an eye. Yet, something remained. 

What truly endured was the growth, transformation, and lessons learned from that experience. It was a pivotal moment that led me to redefine high performance.

Embracing Gifts in Disguise

I discovered that high performance is not solely about external accomplishments but about acknowledging the extraordinary gifts bestowed upon me by my family, the divine, and my community. 

Sometimes, these gifts can appear in peculiar forms. They may come disguised as people who hurt or disappoint us, challenging our perception of their purpose. Yet, in hindsight, these encounters often serve as catalysts for personal growth, self-reflection, and the unveiling of hidden talents.

Action over Circumstances

One crucial lesson I learned from my journey is the significance of taking action. I realized that waiting for circumstances to change or for external resources to manifest can impede our progress. 

So, I decided to start right where I stood, leveraging the resources within my reach to the best of my ability. High performance became synonymous with maximizing my intellect, connections, lessons learned, and personal character every single day.

The Mirror Test

I discovered that true high performance isn’t measured by the number of accolades or the size of our bank accounts. It is measured by the countless moments where we consciously choose our higher selves over short-term comfort. 

By accumulating more instances of saying “yes” to our values, we cultivate a sense of pride in our journey as high performers. At the end of each day, we can look in the mirror and confidently proclaim, “I was a high performer today.”

The Journey of High Performance

High performance is not a destination; it’s an ongoing journey. 

Every morning, I wake up with the opportunity to decide whether I will embrace my role as a high performer or not. I acknowledge my imperfections and understand that stumbling is part of the process. 

What matters is the resilience to get back on track, to start fresh, and to keep pursuing high performance. It’s akin to the journey of fitness, where success lies in the continuous cycle of failing and beginning again.

This is my story—a story that unveils the essence of high performance. It’s about embracing our unique gifts, transforming challenges into opportunities, and making conscious choices aligned with our values. 

High performance isn’t solely about external markers of success; it’s about the countless moments when we prioritize our higher selves over temporary comfort. So, let’s embark on our own journeys of high performance, commit to constant growth, and unlock our full potential.

Transforming Your Assistant From Task Manager to Project Manager

Today, we’re going to explore how you can transform your assistant from a task manager to a project manager, enabling them to take on greater responsibilities and contribute to your business’s growth while giving you more time to focus on your ‘zone of genius’.

Defining Task Manager and Project Manager:

Before we delve into the roadmap for this transition, it’s essential to understand the difference between a task manager and a project manager. 

A task manager is skilled at organizing and managing individual tasks, assigning due dates, and following up on progress. 

On the other hand, a project manager possesses more advanced knowledge and capabilities. 

They understand the entire project lifecycle, including the players involved, industry-specific acronyms, workflows, and the end-user experience. Project managers have the ability to leverage contacts within and outside the organization for support and guidance.

The Roadmap to Graduation:

To facilitate your assistant’s journey from task manager to project manager, there are five key elements to consider:

  1. Well-selected and well-defined tasks: By using the 7 Yes Test and 360 Delegation, you can delegate tasks effectively and ensure that your Assistant receives clear instructions before starting the project.

  2. Motivated coaching: As the leader, it’s crucial to invest time in coaching your assistant, providing supervision, feedback, and training. Coaching is a two-way process that requires commitment from both you and your Assistant.

  3. A motivated and dedicated assistant: Your Assistant should have the drive and desire to take on higher responsibilities. They should possess attention to detail, organizational skills, and a long-term commitment to your business.

  4. Realistic expectations: Recognize that the transition from task manager to project manager takes time. Be transparent about the learning curve and communicate your expectations clearly to avoid overwhelming your assistant.

  5. Sufficient repetitions and feedback: Allow your assistant to gain experience through continuous practice. Offer constructive feedback after each task to help them improve and grow. Repetition and feedback are crucial for their development.

Unlocking the Power of Task Stacking:

Task stacking, a powerful strategy, can accelerate your assistant’s progress. 

By breaking down a project into smaller subparts and gradually delegating them to your assistant, they can gain expertise in each component. Over time, they can stack these tasks together, allowing them to handle the entire project confidently.

A Real-Life Example:

Let’s take a look at a practical example to illustrate the effectiveness of task stacking. 

Suppose you’re hosting a monthly lunch and learn event. Initially, you would define and design the tasks involved, using 360 Delegation. Your assistant would capture the necessary steps in a project management tool, such as Asana, and ensure that deadlines are met. Gradually, you can start handing over specific tasks to your assistant, guiding them along the way. 

With time and repetition, they will become proficient in managing all aspects of the event, from attendee outreach to vendor coordination, leaving you free to focus on speaking and networking.

Signs of Moving at the Right Pace:

Throughout this transition, it’s crucial to gauge if you’re progressing at the right pace. If your assistant feels overwhelmed, there are several possible reasons and corresponding solutions:

Lack of knowledge: Provide additional training and resources to equip your assistant with the necessary skills.

Need for guidance: Offer hands-on guidance by demonstrating tasks or reviewing their work until they gain confidence.

Task size: Break down complex tasks into smaller, manageable components, allowing your assistant to tackle them one at a time.

Unrealistic expectations: Adjust your expectations and give your assistant more time and support to grow into the project manager role.


As an entrepreneur looking to scale your business and regain control of your time, transitioning your assistant from a task manager to a project manager is a crucial step. 

By following the roadmap we’ve discussed and leveraging the power of task stacking, you can empower your assistant to take on greater responsibilities, understand the intricacies of your business, and contribute to its long-term success.

Remember, this process requires commitment and collaboration from both you and your assistant. 

Offer the necessary training, coaching, and feedback while setting realistic expectations. With time, repetition, and gradual progression, you’ll witness your assistant’s growth and see them seamlessly manage projects, allowing you the freedom and flexibility you desire.

At Great Assistant, we understand the challenges entrepreneurs face in finding the right assistant. We specialize in connecting entrepreneurs in early-stage businesses with remote executive assistants who are motivated, dedicated, and capable of growing alongside your business. Let us know if you’d like to take the first step towards transforming your business and regaining control of your time by visiting

The Painful Truth About Hiring Overseas Assistants

I started hiring virtual Assistants nearly 15 years ago.

Since then, I’ve hired all over the world, from here in the US and Canada to the farthest reaches around the world, including India, Pakistan, and the Philippines, to name a few.  To date, I’ve now hired over 700 Assistants.  Some have been a total failure, and some a smash hit.

Early in my career, I thought hiring an overseas assistant was a slam dunk because they were so dang cheap.  When you’re paying only $4/hr, what could possibly go wrong?

Then the headaches started happening.  Big misunderstandings because of the language and culture gap, which meant I had to fix their mistakes over and over.

Then I quickly realized the dramatically different time zones meant it was nearly impossible to meet and collaborate on anything.  This created huge delays that drove me crazy.

Then some Assistants just wouldn’t show up at all.  In one case, my Assistant in India was a victim of government corruption, and the electricity was turned off to her neighborhood.  She was incredible as a worker – awesome English, keen to help, really effective – but that didn’t matter because the environment she was in was so unreliable I couldn’t count on her.

Fed up, one day, I said, “Amateur hour is over!”  I desperately needed a “Mini-Me” type of Assistant who could become my right-hand person, and overseas simply wasn’t cutting it.

So I started looking domestically.  Even though I was stone broke with over $200K in debt and barely making any money – I’d made only $39,000 the year before – I couldn’t stand it anymore.  It seemed unbelievably expensive to pay $15 / hr instead of $4 / hr, but I had to try it.

Within one year of getting a domestic, dedicated Assistant, my income tripled to $107,000, and my productivity quadrupled.  My psychic load was lightened, and I actually started enjoying both my business and my life once again.

As my business grew and I wanted to delegate higher-level tasks such as email inbox and calendar, I realized a domestic Assistant was even more valuable.  Because my Assistant was in the US, I knew I could trust the legal system and the confidentiality agreements I signed with her would be enforceable.  Furthermore, all of my data would exist inside a first-world architecture instead of my most-private information sitting in an unknown office or home in a developing nation where security standards are, how shall we say, “flexible.”


But having a US assistant made it possible for me to hand off these incredibly sensitive yet time-consuming tasks.  Looking back, hiring the right kind of dedicated, domestic, mini-me style Assistant was the biggest productivity jump on my life.  Delegating email and calendar is the second biggest of all time.

I realized: old me thought of getting an Assistant as an expense.  As long as I thought that way, I could never justify getting an Assistant.

But then I realized: even though an Assistant would technically always be an expense, my relationship with an Assistant could become an incredible profit center.  As long as my Assistant was taking over low-level work and I was using that new time to do higher-level, profit-making tasks, I’d always be making way more money than what I spent on an Assistant.

That’s when I realized that being cheap was one of the biggest mistakes I could ever make, and realized I’d only ever hire domestic for the rest of my career.

When it comes to getting a Mini-me Assistant, don’t sacrifice your sanity or the success of your business over a few dollars per hour.  Be smart. Get a Domestic Mini-me. You’ll actually have a shot at fulfilling your potential as an Entrepreneur and as a human.  And that is truly priceless.

Onwards and Upwards,


Properly Training My Assistant Tripled My Income

After I failed with my first five Assistants, I believed training an Assistant was a huge waste of time because they’d just quit.  Plus I could just do it better myself so why bother?

And the math just didn’t make sense to spend 30 minutes training an Assistant on a 10 minute task. I basically gave up on ever getting an Assistant.

Then, one day I was feeling completely exhausted and demoralized.  I’d spent all day working like a madman, yet – ONCE AGAIN – I’d made truly zero progress on my most important projects.

That’s when it hit me that the biggest waste was me.

I was wasting my potential day in and day out dying a slow death, crushed by minutiae of day to day administrative tasks and email.  Something had to change.

So I did a time study, logging every minute of my day. It was an eye-opener. I was wasting so much time on small stuff, while my real game-changing work was on hold.

Reminded me of the age-old quote,

“Hell is meeting the man I could have been.”  

I stared at my time-study and shivers ran down my spine when I realized how much time I was wasting.

I devised a 3 part gameplan which worked perfectly:

  1. Hired a North American dedicated assistant who wanted a long-term opportunity, had the right attitude and work ethic, and was tech savvy.
  2. I found the tasks in my time study which repeated often, were easy to teach, easy to learn, I was already doing myself, and wouldn’t sink the company if done incorrectly
  3. I not only started training, but I DOUBLED DOWN on training my Assistant. Treating her like a long-term investment that appreciates over time.

The result?

Within one year my income tripled and I had more flex time than I ever thought imaginable.

Obviously training the wrong assistant on the wrong tasks is a recipe for failure.

But get the right assistant doing the right tasks and provide them with the right training, and you’ll unleash one of the biggest force multipliers of your entire career.

You’ll also regain the hope that your business is a vehicle to make your dreams come true.

Onwards and upwards

Tim 🙂

3 Ways My Assistant and ChatGPT Supercharge My Business

As an entrepreneur, my journey to managing time and resources more efficiently has been far from easy. 

It’s like juggling balls while spinning plates. 

But here’s a secret weapon I discovered: pairing my assistant with AI, specifically, ChatGPT.

Here are the top 3 game-changing ways we’ve used ChatGPT together:

Content Marketing Magic: 

Content marketing used to be a struggle. From brainstorming topics to keeping a consistent output, it was a daunting task. 

Not anymore. 

Thanks to ChatGPT, my assistant handles a massive part of my content marketing, writing the first draft of all content. Whether it’s emails, blog posts, social media posts, or even speaking points for videos, my assistant creates them all, with ChatGPT by her side. 

The result? 

High-quality drafts that are 65 – 85% perfect, needing only my final touches before they get published to various platforms.

Navigating Sensitive Correspondences: 

Every entrepreneur knows how critical delicate emails can be. A misstep in communication can lead to a crisis. 

Here too, my assistant leverages ChatGPT to craft well-written and empathetic responses, whether it’s a complex legal matter or an upset customer. The result is more effective communication, a speedier response, and with fewer risks.

Demystifying Long Client Messages: 

Consulting often means long emails and reports from clients seeking advice. It can be overwhelming. 

But not with ChatGPT! 

My assistant runs these lengthy messages through it, producing neat summaries and key points. Even better, ChatGPT helps us generate creative and useful replies, often adding new insights that I hadn’t thought of. 

This AI-Assistant partnership has truly elevated my business operations:

My assistant has become a higher-level operator, taking on specialist tasks like content marketing.

It’s streamlined my own time, elegantly summarizing complex situations and facilitating clear communication.

It stimulated my creativity. 

The interplay between my assistant and ChatGPT yields fresh ideas that I hadn’t considered.

In conclusion, if you’re an entrepreneur earning at least $100K/year, an assistant can dramatically enhance your income, impact, and happiness. 

And if you pair that assistant with ChatGPT, you open up a whole new world of productivity. AI doesn’t just supercharge your assistant; it supercharges you. 

Welcome to the future of entrepreneurship