How to Be Self Employed

Self-employment is more popular than ever. Prior to the pandemic, nearly 30% of the US workforce spent at least a part of 2019 self-employed, while 14% of workers reported self-employment is where their primary income came from, according to Gallop’s State of Self-Employment survey created for Intuit Quickbooks.

According to the survey, between 2000-2017, there was a +722% growth in sole proprietors in the US and in 2017, the IRS reported that self-employment was at the highest percentage (17%) since 1957, when they first began tracking it.

The “gig economy” is not only here to stay, but is continuing to increase year after year. Working for yourself is more popular than ever, but that doesn’t mean that it’s easy. Stepping away from your job (working for someone else) to pursue your dreams and build them into a viable business that pays your bills can be quite scary.

And it’s not just the financial concerns. The first time you realize that you can’t walk down the hall and ask Ted in IT why your computer is doing weird things or let Judy in accounting know that the number of dependents needs to be changed on your tax form can throw you for a loop!

If you think constantly being told what to do at your job drains your energy, wait until you have nobody telling you what to do! When you are self-employed, you become very aware that life is scheduled...until it’s not!

But probably the thing that poses the biggest challenge to working for yourself is that nobody ever teaches you how to be self-employed, and if you don’t know how to be self-employed, how can you take your business to the next level?

So what are some of the things that people who are self-employed struggle with and how can you give yourself a better chance to succeed as your own boss?

Jeffrey Shaw was recently a guest on my podcast, Work From Your Happy Place. He is the host of the top-rated podcast, The Self-Employed Life and the author of The Self-Employed Life: Business and Personal Development Strategies That Create Sustainable Success. Jeffrey suggests that almost everyone initially goes into being self-employed for the same reasons; to control their future, their time, and their destiny. But then they realize that they have entered completely uncontrollable circumstances...or so they think.

We talked about some of the challenges of being self-employed and what you need to do in order to succeed in being your own boss.

#1 - Know the difference between mindset and skill set.

You have to have the mindset before you can really embrace the skill sets. Two people can be taught the same process, be given the same materials, and receive the same training yet get very different results; one succeeds and the other doesn’t.

What happened there?

Chances are the person who found success was open to new things, was creative, more enthusiastic, more passionate and let themselves tweak things to make them their own while the other just went through the motions, checking things off the list. The first person was working a healthy mindset along with the skill set, the second was only working the skill set.

Bringing some life and enjoyment into what you do and how you do it is an important component to people knowing, liking, and trusting you. In our interview, Jeffrey and I discussed that being on “the hamster wheel,” where you feel like you are working really hard but not getting anywhere, is a feeling that often happens when you are drowning in a skill set, but lacking in mindset.

#2 - Keep learning, but don’t get sidetracked.

To a self-employed person, everything is personal! What goes on in your personal life affects your business and what goes on in your business affects your personal life. While that might also happen in a ‘regular job,’ there’s no one to step in and pick up the slack when you are having a bad day.

That’s why you have to develop yourself first! Don’t just learn about new social media platforms and self-employed tax codes, continued personal development is what will determine your ability to think big, to be able to work with what you have and prepare for what will come, and to handle both challenges and successes. Those are the things that help self-employed people thrive.

You are your business, and so working on yourself will always be reflected in your work. Pay attention to what you can work on that will pay off and what is just a distraction, and choose wisely. Remember, making sure your personal life has the intention it needs is important for you to be successful. If you are not growing, even success may leave you feeling empty and unfulfilled.

#3 - You control your schedule - that can be great, but also challenging. 

Many people are drawn to self-employment because of the time flexibility it offers. You can choose when you are going to work on your business and when you are going to be available for your kids, family, or an activity you enjoy.

You are in charge of filling your schedule. The upside to this is that you can make intentional choices to ensure that the most important things in your life get your time. The downside to it is that, once you leave a “real job,” you might realize that having someone else tell you what to do with your schedule during work hours was really helpful!

Treat your business like a business by setting up your work hours and creating a dedicated workspace. Create healthy boundaries that make sense for both your life and for your business, and then respect those boundaries just as you would any other commitments you make. A great way to do this is to establish routines.

#4 - Establish routines.

Have a plan, work the plan, and know when to (intentionally) deviate from the plan. Getting up each day and knowing what you are going to do that day will keep you focused and motivated. Working a clear plan will keep moving you forward. However, be careful about becoming so focused on your plan that you miss opportunities because they look a little different than you thought they would (i.e. how they look in your plan).

When you are in focus mode, keep the blinders on, but make sure to take those blinders off occasionally to see what’s happening around you that may be in your best interest to pay attention to or act upon.

Take some time each week to sit back and look at your relationships, what questions you are getting from people, and at any detours or side streets that you might want to explore further.

#5 - Learn the art of networking.

Get in the habit of collaborating, being able to learn from one another, and not just seeing others as competition. Most businesses are about relationships and foundational to the success of your business is to be less transactional and more relational.

Do this not just with your customers, but with everyone you ever work with. You will often find that, when you are supportive, you will be supported. Never forget that a rising tide lifts all ships.

#6 - Be open and ready for changes (because they will happen!).

Getting clear on who you are, what you do, and for whom you do it is necessary for you to be able to focus and commit to your daily routines. You’ll need to get clarity on these things, but don’t get so clear that you self-sabotage yourself.

What I mean by that is, sometimes those things will tell YOU what they’re going to look like - if you keep paying attention. A perfect example is how Covid changed things. My speaking business disappeared overnight, and that had been one of my main revenue generators. If I kept defining myself as a speaker, and only a speaker, my business would have gone under last year. But I didn’t. I “read the room” and knew that in-person speaking gigs were gone, at least for the foreseeable future.

I knew I had to pivot, not just for me, but also for my clients and my employees. How could I serve those people and just have it look a little different? Where could I start showing up for them? How could I make some shifts, still bring value to the people I serve, and be in a position to continue generating revenue to keep my business afloat?

Looking at what is happening and finding the opportunities is very different than “letting what’s happening dictate what you have to do.” When you know who you are and who you serve, you are better able to make your own choices, regardless of the situation.

Being self-employed comes with its share of challenges, but it can be rewarding on so many levels if you learn how to be self-employed. Wake up every day and treat your business like a business, and yourself as the amazing person you are for bringing your own unique value into the world.