I've been working for myself for over a decade—as a content creator, running an online training program, and working as a career coach. Through coaching, I've also supported hundreds of individuals on their self-employment journeys.
I've learned a lot about what it takes to work for yourself, often through trial and error. Now, I want to share the insights I wish someone had given me when I was starting out.
By the end of this article, I hope you’ll feel more clear on if you want to work for yourself, and how to get started.
Here are the steps I’ll walk you through:
Determine if self-employment is right for you
Understand your self-employment options
Set up informational interviews
Plan your transition into self-employment
Create your support system
1. Determine if Self-Employment is Right for You
Working for yourself is often marketed as the ultimate path to freedom and success. We see Satya Nadella and Tim Cook building empires. We see Instagram influencers flying around the world, living their best lives.
But the reality is more complex.
Self-employment can take many forms, and success rarely comes as easily as social media makes it seem.
Now don’t get me wrong—working for yourself can be rewarding, lucrative, and fun. But it’s not for everyone.
So before getting anywhere in this article, let’s first suss out if you and self-employment would likely get along.
Self-employment is not for you if:
You struggle with self-discipline. Good news, you have no boss! Bad news, you have no boss! You have to set your schedule every day and hold yourself accountable to it. This can be very challenging for some.
You don’t enjoy wearing multiple hats. Especially in the early days, you’ll have to do everything. You’re the CEO, lead marketer, lead salesperson, and designer. If you want a straightforward role, this isn’t for you.
You get overwhelmed by uncertainty. In self-employment, there is no one path forward. You are carving the path each step of the way. And it can take 1-2 years to reach a stable income. Are you okay with not having a clear progression?
You prefer staying in your comfort zone. Self-employment means constant problem-solving and facing new challenges. You’ll never stop stretching and learning.
You need a steady paycheck to feel secure. Making money when working for yourself can be volatile. Especially as you’re getting started. There’ll be booming months, and there’ll be months as dry as a desert. Can you be with the ups and downs?
Self-employment is for you if:
Autonomy is a priority. At the end of the day, people drawn to self-employment want creative control, freedom, and independence. If autonomy is a top value, then self-employment could be in your future.
You are resilient. There will be difficult emotional periods, difficult financial periods, and times when your confidence is truly tested. Do you like being tested?
You're comfortable making decisions with incomplete information. You’ll need to build the airplane while you’re flying it. And that requires learning fast and trusting your judgment.
You're open to continuous learning. You’ll need to constantly learn new skills, try new approaches, and pick up new tools. Do you love learning?
You are comfortable with gradual growth. Unlike corporate jobs that often offer faster, predictable progression, self-employment can be slow and can go in waves. Can you hold the long-term vision when things aren’t going as fast as you’d like?
Ok, so what do you think?
After reading those bullets, do you still think you might have the entrepreneurial itch?
If so, then great! Keep reading. I worked a corporate career for over two decades before taking the leap into self-employment.
If not, you might still be interested in starting a side hustle. Or it’s possible that your current job just isn’t the best fit, and you’d benefit from finding a job that you love.
2. Understand Your Self-Employment Options
Before diving headfirst into entrepreneurship, it helps to know what’s out there—because self-employment comes in many forms. Some paths may sound perfect for you, while others might be a horrible fit.
Let’s get a lay of the land.
The 3 types of self-employment businesses
Broadly speaking, there are three types of self-employment:
Service businesses
Product businesses and
Platform businesses.
Let’s go through each:
Service-based businesses
This is when you sell your time and expertise directly to clients.
Examples: Consultants, freelance coders, coaches, personal trainers.
Pros and cons: The upside is that this is the easiest entrance into self-employment. You already have skills; you just need to find people to pay you for them.
The downside is that your annual income is tied directly to your time. So there’s a lower ceiling. Plus, if you’re not working, you're not earning.
Product-based businesses
This is where you create and sell a physical or digital product.
Examples: E-commerce stores, digital course creators, app developers.
Pros and cons: The huge benefit here is that your annual salary is not tied to your time. People can buy your app while you’re sleeping.
The main con is that there’s a lot more upfront work. Want to sell cutting boards? You need to make the product, test it, store it in a factory, market it, ship it. Got a business idea for an app? You need to build it, test it, ensure it’s secure, create an intuitive interface, market it, fix bugs.
Platform businesses
This is when you leverage an existing platform to make money.
Examples: Airbnb hosts, Etsy vendors, YouTubers.
Pros and cons: You get access to a built-in audience with lots of room to grow. Though this route can be competitive, and your freedom will be limited to the platforms branding and policies.
An additional factor: local vs. online
Any business model could be local, online, or both.
Local means you’re meeting with clients face to face. Like a massage therapist or landscaper.
An online business means all of your work is done through your laptop. Like a web designer or an e-commerce business.
Hybrid combines both local and online. This could be a consultant or a career coach.
With that said, let’s get more specific and go over some of the top self-employment job options.
20 popular self-employed jobs
Scan through this list of self-employment ideas and notice which ones stick out to you.
Career coach. It can be rewarding to help clients navigate career transitions and improve their professional skills. Here’s a training to get started.
Consultant: If you have industry expertise, use it to help businesses solve problems.
Freelance coder: Coding is one of the most in-demand skills on the market. Companies or individuals might want you to help them develop software or apps.
E-commerce store owner: Think of an item you want to sell, especially where you see a market gap. Then build a business around that item.
Social media manager: Most businesses have (or want) a social media presence. If you are organized and have digital marketing knowledge, you could help companies or individuals grow their accounts.
Virtual assistant: If you’re organized and on the ball, you could help busy professionals manage their calendars and admin work.
Graphic designer: Design is where art meets marketing. Use your aesthetic wherewithal to create logos, branding, or marketing materials.
Web designer: All businesses have a website. And many websites are lackluster! Learn how to design a website in a way that is visually appealing and effective.
Content writer: Freelance writing can be creatively fulfilling for word lovers, You can write blog posts, product descriptions, and ebooks to help businesses with their marketing.
Personal trainer: If you are passionate about exercise, then start a business where you help potential clients get into shape and reach their fitness goals.
Photographer: Most weddings and events need a photographer. If you get lucky, you could even make a living off more artistic work.
App developer: Build mobile apps. Could be games, productivity tools, or anything in between. You can monetize through either sales or subscriptions.
Digital course creator: Take what you know and turn it into a course. You’ll probably need to build an audience to sell it to. However you could try your luck on platforms like Skillshare.
Dropshipping business owner: This is where you sell products through your online store. You don’t have to worry about product development, inventory, packaging, or shipping. A third party does all that. Your main focus is finding buyers.
Airbnb host: Got a spare home? Or even a spare room? Make some extra money by creating a standout experience for travelers. If you invest in 5-10 units, you could make it you make your full income as a host.
YouTuber: If you can build a big enough audience, you can make money on advertisements and affiliate deals.
Massage therapist: If you’re an embodied person, you might enjoy building a business helping others relieve their physical tension.
Video editor: Most YouTube, Instagram, and TikTok videos need editing. If you can pick up the skills, this is a viable freelancing option.
Landscaper: It’s common for wealthier homeowners to outsource their lawn and garden care. You can make a living if you can find enough residents to serve. Or you can work with commercial clients, who tend to pay more.
Shop owner: Think brick-and-mortar. You could start a retail shop, café, or restaurant.
Did any of those ideas light you up?
3. Set Up Informational Interviews
If you want to run your own business, the best advice I could give is to conduct informational interviews before getting started.
Based on the list above, what routes of self-employment appeal to you?
Let’s say, just for example, that you’re drawn to freelance coding and course creating.
If that’s the case, I’d suggest you reach out to 5, 10, even 20 freelance coders and course creators.
Set up 15-minute conversions. And pick their brains!
What do they like about the work? What do they hate? What advice would they give you? What would they do differently?
Doing this extra homework will give you tons of clarity and a huge leg up for if you decide to get started.
4. Plan Your Transition into Self-Employment
Moving from employee to self-employed comes with a financial shift. Take these questions into consideration:
What are your living expenses? Get crystal clear on how much your life costs each month. In other words, what income do you need to hit if you work for yourself? Also, bear in mind that when you run a business, you typically owe tax money at the end of the year (rather than get a return) and have to pay for your own insurance.
When do you want to quit your job? It’s often a good idea to get started on your self-employment venture before quitting your current role. Then, when you feel ready, you can take the leap into full-time self-employment. But how much progress do you want to make on your business venture before you feel ready to quit?
How much extra buffer do you want in place after you quit your job? After you quit, how much time do you want to give yourself to start making consistent money in self-employment? Do you have enough money put aside to go without profit for a year? Two years?
What should you do if you don’t make X money by Y date? There is a possibility that youre business won’t get up-and-running in that year or two. While not ideal, it’s good to have a contingency plan for what to do if this happens.
Once you’ve answered these questions, you’re all but ready to move forward into self-employment!
5. Create Your Support System
Success in self-employment often depends on building a strong support network. While the independence of self-employment is liberating, it can also be lonely, and intentionally crafting a support network can be your saving grace.
Here are three ideas for building a support system:
Join or create a mastermind group with other entrepreneurs. Set up regular meetings to share challenges, brainstorm together, and hold each other accountable.
Find co-working buddies. Either virtually or in person. Working alongside other self-employed people can give you extra motivation and structure.
Work with a career coach. Especially if you’re still on the fence of going into self-employment or not. A coach can help you get clear on what you want for your career and help you move toward your goals. You can find a coach here at the International Association of Career Coaches.
The path of self-employment might be independent, but that doesn't mean you have to walk it alone. Having some allies, thought partners, and accountability buddies in your corner can make all the difference.
And if you’re still not sure what you want out of your career, a career coach could help. Just fill out this form for free and we’ll match you with a handful of certified coaches for you to pick from.