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TT#050 - If you gave me a time machine…

Feb 21, 2023
TT#050 - If you gave me a time machine…

It took me 36 months to consistently break $40k a month in client sales. 

But if you gave me a time machine, I could go back and do it in 25% of the time. 

4 mistakes slowed me down. And they’re the same mistakes that I see solopreneurs make on a daily basis.

This newsletter is my attempt at helping you avoid those very same mistakes.


1: Solved Problems That Didn’t Exist

For the first 6 months, I was in problem solving mode. The issue was that a significant portion of the problems I was solving didn’t actually exist - yet.

I spent hours working on a complex tech stack: a mixture of tools that were going to help me manage leads for the next few years.

But the leads weren’t coming in yet. 

And by the time they were, I’d found a better - and simpler solution. The problem that I’d spent so long solving never materialized. 

And that’s the punchline:

Things are going to change quickly in your business. You’re going to iterate and change as the market gives you more feedback over time. 

Don’t overthink it. Just address the issues as they come up. And when you start seeing your sales creep up, you’ll have the momentum and headspace to start thinking further ahead.

Simply put: if you're under a million in sales, the here and now is what's most important.

And the best way to avoid getting stuck solving problems that aren’t gonna happen? 

Clarify and address the ones right in front of you.


2: I Delegated & Outsourced Too Early

I came into the solopreneurship game as an executive. Delegating and outsourcing is in my blood. 

But looking back, I can’t help but cringe thinking about the number of freelancers and agencies I hired, only to never use their work. 

“But Ray, you paid good money for their work. Why didn’t you use it?”

I thought I was outsourcing execution. A good idea for the most part.

But because I was just starting out, I was actually outsourcing key decisions. To freelancers and agencies that didn’t understand my business. 

There are 3 areas I see people most consistently outsource too early:

  1. Marketing funnels - Your funnel is how you live or die if you have an online business. You need to understand what makes your funnel perform well and perform badly. And you’ll need to know how to make changes until you have some traction.
  2. Copywriting - Until you’re certain of the language your clients respond to, you can’t outsource the writing process. If you do, you’re outsourcing your message development to somebody with little to no understanding of your audience or the problem you’re solving.
  3. Sales - You want to be talking to prospects all the time. Hearing their questions and objections is invaluable R&D, and sales calls are an effective way to understand how they describe the problem you’re hoping to solve. 

Outsourcing too early slows you down because you’re not learning quickly enough. And if I could do it all again, I’d hold off trying to outsource these key functions. 

3: I Didn’t Invest Early Enough

This was the classic chicken and egg scenario. I fell into the normal reasoning:

“After I get some more sales, I’ll start investing in upskilling myself. Especially around funnels and social media.”

But that thinking actually set me back. I understood that I wouldn’t get my sales up until I upgraded my funnel, but I couldn’t justify doing so until I’d got my sales up.

Eventually, I took the leap and invested 2 months worth of sales into a course. And 10 days after implementing the material, I’d made my money back.

Here’s the thing: 

When you invest in yourself, it's going to fast track your success. But there are two caveats:

  1. Be selective, and invest in the bottlenecks slowing you down. There’s no point going from ‘good’ to ’great’ on sales when it’s your lack of marketing expertise stopping you.
  2. Make sure you’re working with somebody credible. Have they repeatedly done what you want to do? Do they have proof? 


4: I Allowed Perfectionism To Slow Me Down

Perfectionism is tough to avoid, especially when “we’re” the brand, And we’ve got friends and former colleagues (not to mention prospective clients) all watching. 

I was no different. I struggled to shake perfectionism for my first 12 months as a solopreneur. 

Here’s what it meant: I was reluctant to release anything that I felt wasn’t “good enough.” I delayed a bunch of high leverage actions until I felt like I could execute them perfectly. And I wasn’t nearly as experimental as I should have been.

There was a voice in my head that would say something like:

“Well, what’s so-and-so going to think? What if this thing flops? Or what if no one buys it?”

But perfectionism is just fear. And candidly, you won’t get to the next level with a fear-based mindset. 

If you’re lucky, it slows you down. But in many cases, it can keep you stuck at the same kind of income level indefinitely. 

The ‘circuit break’ for me was actually relatively simple. I started asking:

“Does the person I'm concerned about right now have what I want?”

“And if not, why do I give a shit?”

The key recognition is that nothing is going to be perfect, but equally, perfection isn’t required. 

As one of my coaches has always told me, action leads to insight more than insight leads to action. 

And the more intentional action you take, the more progress you make. 

I’m on a mission to help 10,000 entrepreneurs build a business that helps them unlock the lifestyle they truly want.

Limited Time: Check out my free 5-Steps to Build A Scalable Lifestyle Business training. 

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