Not everyone is cut out to work for a large company. Some of us are better suited for self-employment. While it can be overwhelming, we've created a checklist of topics and skills to gather as you embark on this journey.

Before we dive into the checklist, check out our strategic thinking guide. Here's a master guide of great strategic thinkers, the do’s and don'ts, and professionals who can benefit from learning more about how to plan for the future.

Strategic Thinking Skill Guide | Definition and Examples | Matter
Strategic Thinking is developing effective plans that are aligned with a company’s mission. Learn what is strategic thinking, examples, and how to improve it.

The pros and the cons of working for yourself

A 2019 Gallup survey found that nearly 30% of Americans are self-employed. Part of the pro side of self-employment as a career is the sense of independence and autonomy over how and when they work is the biggest factor.

Independence is the biggest benefit of working for yourself. With self-employment there's the freedom and flexibility to work on your terms, dictate the location, hours of work, and how to approach work.  

On the flip side, working for yourself can be quite challenging. Cons include having no pre-established support system, go-to colleagues, and paying for your expenses. And you may experience inconsistent income as you grow your business.

If you are looking for a behind-the-scenes glimpse at self-employment, check out NPR's podcast "How I Built This." Host, Guy Raz, chats with company founders about the unexpected paths they each took when building their companies.

How I Built This with Guy Raz
Guy Raz dives into the stories behind some of the world’s best known companies. How I Built This weaves a narrative journey about innovators, entrepreneurs and idealists—and the movements they built. Pre-order the How I Built This book at https://smarturl.it/HowIBuiltThis.
Guy Raz talks to founders of now-famous companies about their humble beginnings in creating a business.

Consider this when planning to work for yourself

Here are some questions to help you visualize your life when you make that leap into self-employment. This will help you take your dreams out of the ideation phase into planning.

  • What does my day-to-day involve?
  • How much do I work?
  • Have I weighed out the pros and cons?
  • Where do I want to be 6 months from now? A year?
  • What happens if my plan goes wrong?
  • Where will my clients come from?
  • What does success look like?
  • What haven’t I considered?
When it comes to working for yourself, weigh all your options for the maximum growth potential. (Illustration by Gaspard Bonne)

Key skills needed for self-employment

While there are many skills required for a self-employment, we've picked out the three most vital skills you need to be successful: project management, multitasking, and communication.

Project management

Project Management is an essential skill to ensure all tasks are carried to the finish line. You don't get assigned projects, tasks, or deadlines, so it's crucial that you're able to create your own structure and stick to it. That means adhering to your own deadlines, criteria, and budget.

We don't all have to be a PMP (Project Management Professional) like Amy Hamilton in order to leverage simple management tools to make us more resilient at work and in life. (Video from YouTube)

Multitasking

Part of being successful, is learning how to be a master multitasker. You'll have your hands, legs, toes, and fingers in every aspects of the business from the quarterly roadmap to the pens on your desk. While it can be overwhelming, TED Talk speaker, Tim Harford, shares his tips and secrets on multitasking effectively.  

Tim Harford discusses how to use multitasking to help, not hurt, your daily tasks. (Video from YouTube) 

Communication

Many people choose to work independently because they think this will allow to communicate less. However, tactful communication is still necessary because how you relate to your customers will directly dictate your company. Whether you're sharing your company values, engaging with clients, or asking others for help, communication is at the heart of everything you'll do.

Casey Brown, a pricing consultant and business owner, discusses how to ask key value questions that help you understand your relationship with potential clients when being self-employed. (Video from YouTube)

Last considerations when working for yourself

You're almost there. But before you start this journey, consider these final tips and thoughts as you pursue self-employment.

Have a plan. The best way to become self-employed is sketch out a plan. Think about the market, competitors, and a backup plan. Even if your first try doesn’t work, embrace it as a learning experience.

Have benchmarks in place. May sure you have built-in checkpoints to help you gauge your progression towards your goals. Feedback is key to improvement, and self-employment is no exception.  

Crunch the numbers. A financial safety net is imperative to have in place. Ask yourself these questions: How much will I need to have saved before I start my new venture? What are the overhead and recurring costs that this new business will incur? What if I run out of money?

Go for it!

Embarking on a self-employed career can be incredibly rewarding. There's no question that you'll have to roll up your sleeves and put in the work. But remember: You'll be chasing your passion on your own terms.


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Cover Photo by Oleksandr Aleksandrov