In the lead-up to quitting my nine-to-five back in August 2016, the question of how to become self-employed plagued my thoughts.

I had been working in corporate finance at the time. And, as you might imagine, I was bored out of my brain. 

I was tired of staring miserably at mind-numbing spreadsheets all day and wishing desperately that our systems would crash so I could go home early. 

I craved a drastic career change. 

Fast forward to November 2018, and I was officially (and gainfully) self-employed. I had quit the hospitality side gig (that’d helped pay the bills.) I’d stopped searching online job ads. And I felt comfortable enough with my finances that I could finally breathe.

I was the happiest, most productive, and most fulfilled I had ever been. 

But getting from point A (the soul-sucking corporate gig) to point B (working for my mentors with the flexibility and freedom of a freelancer) was no easy task. 

And today, I want to shed some light on how I got to where I am now. 

Become self-employed with the help of self-discovery

“Each person has a greater potential for success in specific areas, and the key to human development is building on who you already are.” – Don Clifton

Aside from a wonderfully supportive husband (who kept us fed and watered when I couldn’t), developing self-awareness sits at the top of everything I have been able to accomplish in my online career. 

It’s helped me conquer procrastination, perfectionism, and plenty of other obstacles that I had previously allowed to stand in my way. 

Simple self-discovery gives you the confidence to step outside your comfort zone and take on self-employed challenges you previously may have dismissed as “too hard.” 

Self-awareness is a superpower (especially for the self-employed)

By uncovering your: 

  • Strengths 
  • Weaknesses
  • Natural tendencies, and 
  • Best ways to use your energy and expertise 

… you gain eye-opening (paradigm-shifting!) insight into who you are and how you like to operate. 

So, before we dive into some of the more business-related strategies I’ll share with you, here are five of my favorite ways to learn more about yourself. 

Moving past the profound power of self-awareness and the catalyzing effects of curiosity, there are some more specific actions I took to shift off the corporate conveyor belt and into the world of freelancing. 

Of course, there were plenty of mistakes and wrong turns in finding (and implementing) these strategies and systems.

But in the hopes that I can reduce the time it takes for you to find your own “freelancing groove” and help you bypass ground zero — I want to share the things that worked. 

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Key move #1: Self-directed learning

I spent oodles of time learning new things when I first discovered online business. 

The problem was I wasn’t implementing the impactful stuff. I fell for “shiny object syndrome” or procrastinated on the hard stuff. Sure, the courses I bought were great, but all I did was consume — never create. 

That is until I adopted the concept of “just in time” learning.  

How to strengthen your skillset, stack your talents, and focus your learning

“Just in time” learning is about focus. When you focus your studying so you can implement it as you go, you can turn what you learn into a sellable skill and use it directly in your business or next career move. 

I learned “how to learn” a little too late for my liking (and managed to rack up some significant debt from being so unfocused). But once I figured out how to weave what I learned into my projects to achieve my goals, my results started to change. 

If you’re like me and love to learn — but get stuck on actually implementing the lessons — I suggest shifting into “just in time” mode. Focus on one thing you want to improve, understand how it will directly affect and drive progress with a current project you have, and use it to help you become self-employed. 

Yes, it pays to invest in the right education. But it’s a waste of time and money if you don’t take the necessary action to use what you learn. 

(If you struggle with implementation, this will help!)

Key move #2: Relationship building

The word networking churns-up icky feelings for me. And because of my distaste for it, I rarely set foot at networking events. 

I do all my connecting and communicating online. And for the most part, I focus on connecting with the people I love to learn from. 

Back in 2016, I had never met any of my online mentors. But now I’ve worked with two of them! 

Brian Clark and Sonia Simone have taught me so much over the years. And just by being present, genuinely curious, and eager to add value to their work, I was able to build those relationships into opportunities that changed my life. 

Bear in mind that both these relationships started completely one-sided. But as I slowly-but-surely developed my connections, the possibilities started to present themselves. 

How to build genuine relationships with your mentors (and turn them into paying clients)

If you’re wondering how to open these doors for yourself, here are a few things I did:  

  • Signed up for my mentors’ email lists and read their blogs.
  • Used Twitter to stay on their radar (a less crowded place for networking than Facebook or Instagram).
  • Bought their courses and eagerly learned from them. (They were doing what I wanted to do, so it made sense).
  • Developed my skills (and paid attention) enough so that I could offer value to them in the future.

These are simple steps, but they take time. And while most of us look for quick fixes and shortcuts, playing the long game has always produced better results for me. 

The digital world makes it effortless to connect with people you don’t know (but want to). And as long as you’re consistent, genuine, and aren’t looking for them to give you anything in return, the opportunities are endless. 

Key move #3: Guest blogging 

Marketing was the most difficult concept for me to grasp when I first started my career online. In fact, a lack of marketing is why my first business ventures failed so epically. 

I am not a natural salesperson. I hate rejection and don’t enjoy that side of the business at all. 

But I learned from my mentors that there are better ways to sell than the “in your face, pick me, pick me” style I was aware of. 

As an introvert who prefers written communication, discovering content marketing was a huge “aha” moment for me. And learning this alternative way to sell and market myself led me to where I am now. 

How to ease your self-employed marketing fears by using a strategy that makes sense for you

Guest blogging is my favorite marketing and traffic strategy. And coupled with smart email marketing, it’s a killer combination for any solo business operator. 

But most importantly, it was the content marketing strategy that worked for me. Mainly because the writing was something I really wanted to do, and that desire meant I was willing to invest the time, energy, and resources it took to develop the skill. 

And, of course, my career benefitted from my writing goals too. 

After all, guest blogging was the strategy I used to start writing for Brian on Further, which led to working with him on Unemployable. And getting hired at Copyblogger.   

Using a marketing strategy that fulfills you creatively and exercises your strengths will produce better results than one you force yourself to do because you “should” do it.

It also makes it easier to push past the fear and procrastination and achieve the results you want.

Key move #4: Personal Kanban for the self-employed

Self-management is a struggle for almost every freelancer I’ve met. 

But luckily, it’s a skill you can develop. And when you find a system that sticks, it can transform the way you work.  

In my search for productivity superpowers, I found that I needed my most important tasks out in front of me, screaming at me to get done. And this is where Personal Kanban shone through. 

It’s visual, tactile, and completely in your face. Plus, you get to play with Post-its. 

How to skyrocket your productivity with a self-employed management system that sticks

Personal Kanban is how I manage myself and my projects. It allows me to focus on the work — not the organization of the work — which makes progress and getting results significantly easier. 

If you struggle with getting things done and want to feel more on top of your work, you might like to try Personal Kanban. I’ve written more detail about how it works and my experience with it here.

As a freelancer (or anyone with side projects or a busy schedule), your self-management strategy is at the core of how much (or how little) you can accomplish. So invest the time in creating a system that works for you. 

Key move #5: Develop a support system

On any challenging journey, we’re confronted with obstacles that we don’t yet know how to overcome. It can get frustrating and overwhelming.

And as you work your way through the solution, there are times when it feels like you will never find it.

How to be self-employed and position yourself for growth

This is where a fully-rounded support network becomes critical. Because stacking your support system is what’s going to get you through the tough times. 

  • Find yourself a mentor,
  • Look into getting a coach, 
  • Seek out a community that can help you problem solve, and 
  • Get yourself a “business buddy” to bounce ideas off and brainstorm with. 

Most importantly, surround yourself with action-takers. The more you see others around you doing things, the more you’ll want to do things too. 

If all of this sounds like what you need, Copyblogger Academy might be the perfect place for you.

Bonus: Commit to course correction 

Before I started freelancing, I had two failed “businesses” under my belt. 

The first was just a terrible idea and product, and the second I never managed to monetize because I let procrastination and a fear of selling get in my way. 

But those failures (and the lessons I learned from them) lead to working for Brian at Unemployable, working on the Copyblogger editorial team, and countless other opportunities for working with other wonderful creators.  

“Having a growth mindset won’t make you successful, but not having one will prevent you from trying in the first place.” – James Clear 

Embracing a growth mindset reminds us that mistakes and missteps are a part of the learning process. And committing to course correction is how you can move forward again, perhaps with a different approach, a new strategy, or a deeper understanding of what went wrong and why.   

The road is long — don’t rush the journey 

It took me two years from quitting my corporate job to become gainfully self-employed. And I spent another two years before that learning everything I could to level up my skillset and change my circumstances. 

It feels like a long time, but in the grand scheme of things, four years is nothing. 

I’d rather struggle on the road to heightened self-awareness and work toward goals that mean something to me than stay stuck and miserable in a career where fulfillment, joy, and, most importantly, growth aren’t on the menu. 

If you’re struggling with your next move, worrying about your future, or feeling stuck in your current situation, consider getting to know yourself better. 

Self-awareness is an incredibly easy first step. And once you develop that keener sense of who you are, how you like to work, and what you’re truly great at — the path forward to becoming self-employed becomes remarkably clear.


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