Filling gaps in your skillset: How to go about learning and upskilling yourself

I’ve met a lot of business owners and entrepreneurs who knew absolutely nothing about business when they started. These are often my favourite kinds of entrepreneurs to meet. They have a hunger for knowledge and an itch in the world that they absolutely had to scratch.

By: Nic Haralambous

“Bootstrapping your idea” is a series of 6 articles by serial entrepreneur and LifeCheq client Nic Haralambous. Nic has to date started 8 separate businesses, including a social network, a campus newspaper, a retail fashion company and, at one point, a rock band. In this amusing and insightful series, written exclusively for LifeCheq, he shares the most important lessons he has taken away from both his successes and failures. A must-read for the aspirant entrepreneur, or anyone who wants to take their passion project to the next level.

I’ve met a lot of business owners and entrepreneurs who knew absolutely nothing about business when they started. These are often my favourite kinds of entrepreneurs to meet. They have a hunger for knowledge and an itch in the world that they absolutely had to scratch.

When they decided to build their business there was nothing that could hold them back, even not knowing the basics like how to invoice a client or build a sales pipeline.

Fear Prevents Learning or Starting

Back in the day there really were only one or two ways to “learn about business”. You could either find a mentor and work in their business and watch them over many years then leave and do it yourself or you could pay through the nose to get an MBA and hope to goodness that the piece of paper telling you that you are capable is actually right!

Today things seem to be a lot different. Barriers to starting a business are much lower, costs are lower and there are so many more things that you can actually do that it can be overwhelming.

Before Wikipedia and the Google machine there was no single, centralised place for aspiring entrepreneurs to gain knowledge quickly. I’m a fan of trial and error learning but I like to be trying and failing at the most relevant thing. How do you even know where to start when you don’t even know what you don’t know?

Start with the suffering

If you are unsure about what you should be learning first then I suggest you take a look at the one thing that is causing you the most trouble or, as I like to say, burning the fastest in your business.

Are you struggling to invoice people? Are you battling to keep track of your sales and who you’ve contacted already? Are you unsure how to make the accounting “just work” in your small business? It could be that you are battling with HR or website issues or even just figuring out how to apply to be a vendor at one of your clients. There really is so much stuff to battle through that it can be overwhelming and just the thought of it all makes you not want to even start.

This brings me to a rant: I need to illustrate my frustration with people who are waiting for someone to show them, teach them or educate them. You hold the world’s information in your pocket; don’t wait for someone to teach you. Don’t wait for that perfect teacher or mentor to come around. Don’t torture yourself with a lack of knowledge.

You need to ask yourself: “What am I waiting for?”. Why are you waiting for someone to teach you when you have a YouTube video with an instructor for free and on repeat? Improving your skill set lies in determination not access to information. You’re probably waiting because it’s easier than learning. It’s easier to turn on Netflix than learn how to play chess. It’s easier to watch a movie than to learn how to code. If you’re taking the easier path then you probably don’t really want to upskill yourself or learn anything new.

Dedication is so important when you have access to every distraction out there that it’s more important to say no to the distractions and be dedicated yourself to the learning.

Which gaps to fill

The difficult part for me is figuring out what I want to learn today and then being dedicated to learning that skill.

There is always a concern for me when upskilling myself that I am becoming distracted learning something that is not core to my requirements or preventing me from becoming an expert in a field. Too much diversification (in any sense) can leave you with a shallow pool of knowledge and no depth to become exceptional.

This leads me to the concept of a T-shaped person or phrased another way, a jack of all trades and master of one. From Wikipedia: “The vertical bar on the T represents the depth of related skills and expertise in a single field, whereas the horizontal bar is the ability to collaborate across disciplines with experts in other areas and to apply knowledge in areas of expertise other than one’s own.” Specialise but diversify your skills so that you are better equipped to engage across various disciplines.

Right now you should be thinking about your own career, skill set and choice and figuring out if you are doing the thing you want to be doing for the next 5 to 10 years. If you are content with where you are then you can start to add new skills that compliment and assist in diversifying your options. If you’re a doctor, do you want to learn how to manage the money you make a bit better? If you’re a professional athlete do you want to understand the body better? Figure out the gap you want to plug by analysing what you are doing right now and then branching off in an adjacent (but connected) direction.

If you’re in a business and have a variety of skills that could help you level up then you need to ask yourself which pain point is the absolutely most important one causing your business trouble or holding you back. Figure out the itch that is driving you mad, keeping your customers unhappy or might really boom your business if you can scratch it. Then get learning.

Where to Start

Since there are so many different ways to learn and places to learn from today it’s important to start out really simply and do you research.

Head to google and search for the thing you want to know. Let’s use an example of learning the basics of search engine optimisation. I’d search for: “Learning SEO”. Here’s what google came up with.

Google results for SEO

You can see that the first 4 results are ads and you can choose to click those and learn more about the service being advertised. Then you find a variety of results that you can investigate that are organic. Dig into these links, learn the lingo and start to build up your basic understand of the industry.

I often suggest that people find an industry expert and talk to them about what is important to know as a beginner.

Once you feel you’ve gathered sufficient knowledge from the available free resources that google shows you, I would move on to some guided videos on Youtube.

Head over to YouTube and search for the same thing: Learning SEO.

Youtube videos on SEO

There are over 350 000 results for this search. That’s a lot of learning. Find someone you like to listen to, check if they have a wealth of resources and videos, and have a decent reputation, then start watching their videos.

Online Courses

Studying no longer requires a lecturer in a building at a university. Firstly, many universities have made their courses available online for free. Over the past 6 years almost 800 universities have made some of their courses available online for free. These courses are collectively called MOOCs or Massive Open Online Courses. See what I mean when I say there are no excuses?

If you don’t want to sift through these courses then you should try online learning platforms like, or They all offer a vast array of courses you can take and actually receive proper qualifications for completing.

Learn from your peers

One of my favourite ways to learn is to ask my smart friends about the thing I’m trying to learn. Either they will be able to help me or know of someone who can assist me or put me in touch with someone else who has a clue.

I like the tangible act of meeting people, creating a support network and learning from other people’s lessons.

In his book, Tools of Titans, Tim Ferris talks about a theory of learning that I love. The basic premise is that the best way to learn involves someone that you can learn from, someone that you can practice with and someone you can teach. By the time you are trying to teach someone you will know if you have learned the topic or skill sufficiently. If you cannot teach someone the skill then you probably don’t know it well enough (or don’t want to).

Don’t be afraid

When I was a kid my mom would ask me to fix the internet or the printer whenever either would stop working. After a few years of managing this I just outright refused to help. I instructed my mom to call the helpline and ask them to show her how to do it. Why? Because that’s how I learned. I wasn’t afraid to ask for help and to appear stupid. I used the resources that were at my disposal (a helpdesk) and I called for help and listened and learned.

After a few months my mom realised that she was fixing the internet on her own and the printer didn’t need my help any longer.

Knowledge makes you self-sufficient and the sooner you realise the power that it brings with it, the sooner you can get over your own insecurity and start learning.

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