In my own experience and experience working with people who quit the corporate world to work on their own, I have found five consistent themes that emerge with most of these people. Most don’t plan these five things, but looking back there is an element of each in people who take the leap to self-employment.

#1 Make A Friend Taking A Different Path

People who take a leap often cite a strong influence that gave them proof or the courage that they could do something different. For some, this person is in their own family — a parent or grandparent who lived and worked on their own terms — often an entrepreneur. 

It can also be someone you meet serendipitously. On my podcast, I talked to Lydia Lee, who had a meaningful conversation with someone who was living and working nomadically in Malaysia. It told her that this kind of life was possible, but more importantly, told her that her circumstance in the corporate world was not the only path.

This “friend” can also turn into a partner. Some people find that they want someone else to join them on this journey. This is often the case in entrepreneurial ventures where someone is starting a business. Having a co-founder not only makes your path seem less crazy, it can also be more fun as you learn and grow.

#2 Redefine Money

Everyone who pursues self-employment has to face their emotional relationship with money at some point. 

A paycheck from full-time employment is a rather peculiar arrangement if you frame it in the entire history of humans. In self-employment, you shift away from this arrangement and instead of getting paid a steady income for performing the duties of an employee (showing up, being available, doing good work) you will be getting paid for work you find, things you sell or projects you complete.

There is often an “a-ha” moment when people start a journey of self-employment that has them suddenly look at their expenses instead of their income. People realize any spending means more paid work needs to be done. People will often start taking active steps to lower their cost of living or if they aren’t willing to compromise a certain lifestyle, look for more ways to make money or charge more for their current work. 

The self-employment fear setting exercise I created can help you grapple with some of your money insecurities by explicitly stating the least amount of money you are comfortable making and how long without paid work you are willing to go. This reflection may even tell you that you don’t actually want to make the leap.

#3 Build A “Say No” / “Eff You” Fund

Build up some cash savings. This can build on #2 — you may find that you can dramatically cut your cost of living for several months to build some savings. Having savings for your leap enables you to “pay yourself” when you want to say no to a project that might drain your energy or even take a few months off to work on a creative project that is calling you.

Mohit Satyanand built his own fun by aggressively saving early in his career:

I chose to be different very early. Within a year of joining the ranks of management trainees at a multi-national corporation, I realised that I was not meant to be a corporation man, that I needed to live in nature, to watch the peaches grow. In my spare time, I drew up business plans to run a dairy farm, or drive a tourist taxi. Most importantly, I realised I needed to build up a war-chest from which to fund my freedom. My F*** You Fund, I called it.

Even if you don’t have massive savings, dealing with a dwindling savings account can be a way to stare face to face with your fears and to bet on yourself. Despite my savings, I went through a several month period early in my journey where I didn’t earn any money. I felt terrible, but it also helped me realize how much pressure we put on ourselves to fit into a standard narrative of success.

It might even be helpful to look at your journey as a sort of Master’s education in life. Even if the leap doesn’t work out, many people find that the experience helps them deal with uncertainty, gain confidence in their work and in many cases if people decide to return to work, return in a better and higher-paying role with a bit more wisdom.

#4 Teach Others

We all have so much knowledge than many would die to know. What about your path or journey in life is different? How can you teach that to other people? I recommend creating a list of 25 things you might be able to teach people. This can be as simple as a new way to fold shirts or as complicated as theoretical physics.

One way to put this into action is to write about something you know. An article could be “Here are 5 Things You Should Know About X.” Writing it will have the dual impact of forcing you to learn it at a deeper level and put something out in the world that people might respond to. You may find that others are hungry for the insights you have to offer which gives you a clue to keep following that path.

Another option is to post on social media or e-mail your connections and give them a list of five things you are passionate about sharing with others. I suggest posting something like this:

Hello friends!

I’m doing a fun course online where I’m pushing myself outside of my comfort zone and experimenting with new ways of working. I’m doing a challenge this week where I need your help. I am looking for someone that wants to learn. Here are a few things I know about that I would love to teach you more.

1. XXX

2. XXX

3. XXX

4. XXX

All I ask is that you give me $25 for the “lesson” — this is to keep us both accountable and to raise the stakes on myself so I don’t disappoint you. If I do disappoint you, its $30 back to you so you can enjoy a free coffee on my dime.

Who wants to learn something? Message me

I suggest charging to help you stay accountable and it will help you with #5.

#5 Experiment & Get Paid

You need to have some evidence (for yourself and your confidence) that you can literally go through the process of getting paid for something outside of full-time employment. 

One easy idea that most people can do is to host a topic-related dinner around a certain theme and gather 8–10 people for high-quality food and conversation. People crave these kinds of intimate gatherings and are more than happy to pay $15–20 (or even more depending on the food).

We often underestimate our own networks and the people that may want to work with us. Many people feel bad hitting up their connections and asking them for help with their work, but find that these are exactly the people that want to support them. Plus, people could be waiting to be helped by you but didn’t know there were people in their network that could help.

Here is an example of an e-mail I sent to 100 friends and family that led to two clients hiring me. It was terrifying accepting payment from clients, but it gave me the confidence to experiment further. While still employed I got paid for two speaking gigs, a group coaching event and by several private coaching clients. These were all small fees but gave me confidence that I could make money on my own.

Don’t worry too much about the pay. A pro-bono engagement can be just as rewarding. I did multiple pro-bono coaching and consulting engagements before taking my leap, but treated them as serious commitments. I asked the same of my clients and that they offered generous feedback during and after the experience.

People underestimate the opportunities that are available to them. We are trained to think that we need to find a job before we can start doing something. However, if you are truly passionate about something and willing to offer it for low or no-fee, people are usually more than enthusiastic to be part of your learning journey. For example, if you want to start freelance consulting, you could send this message to an organization you admire:

Hello, I’m a big fan of your organization and have enjoyed how you have focused on X over the last year.

I’m currently in the process of making the transition to freelance consulting and am looking for a couple of initial clients to work with. I wanted to see if you’d be open to a low-fee or pro-bono project where I help you work on Y.

Given this is a path I’m incredibly excited about, I’ll be taking this very seriously. All I ask is that you are generous with feedback and be very direct in helping me determine if companies would be open to paying for this type of work.

Most companies would jump for the chance to work with someone with such initiative and desire to learn.



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