25 ways to be your own boss

Working 9-5 can be a drag, especially when today’s workplace expects you to be connected even beyond those hours - and all for a paycheck that seems to cover fewer and fewer of your bills each month. It can be extremely difficult to motivate yourself to work hard knowing that a lifetime of labor doesn’t even go as far as it did a couple of generations ago. 

Worse still, you have to work when your bosses want you to work, and you even need to ask permission for simple things like taking time for a Doctor's appointment. Life as an employee can feel as if you no longer have freedom or control.

Luckily, grinding your way up the corporate ladder isn’t the only route to a life where you don’t have to worry about those things. Even if you’re paycheck-to-paycheck right now, you absolutely can pull back control of your professional life by becoming your own boss.

So, how easy is it to become your own boss, and what options are there for aspiring entrepreneurs? We’ll reveal all that and more in this guide, and give you 10 simple steps with which you can plot your journey to becoming your own boss. Let's start by looking further into why you may want to break free of the 9-5 and be your own boss.

Why Be Your Own Boss?

So, why exactly would you want to become your own boss? Here are some of the main incentives:

• Freedom and control
  One of the main advantages to being your own boss is the freedom to work as and when you want to. Whether this is to fit your personal situation or just create a better work-leisure balance, there isn’t a manager figure or company dictating terms to you any longer. 
• Do what you love
  Passion is something that the vast majority of people lack when it comes to their job, to the extent that only a very lucky few can claim to actually do something that they enjoy, let alone have a passion for. By doing your own thing and becoming your own boss, though, you can choose to do whatever you truly enjoy doing.
• Unlimited earning potential
  When your business starts to become successful, your earning potential can quickly outstrip what you might expect as a salaried employee. It’s entirely possible that you can add multiple zeroes to your income in a couple of years by becoming your own boss, and how much you take home depends on how you structure your business, not on an arbitrary worth that a company sets on your labor. Check out these stories of sellers on Whop to see just how much they earn by being their own boss.
• Sense of achievement
  Human beings have a natural drive to create and achieve, and establishing a successful business can be an incredibly fulfilling journey.

Disadvantages of Being Your Own Boss

As enticing a prospect as it is, being your own boss does have a few drawbacks. Some of them are:

• Income inconsistency
  Despite the lack of an upper limit on your earning potential as your own boss, you aren’t going to be raking in the millions in your first month or even year. You might not see a single cent as you plan and get your business off the ground, and things can be very difficult in a financial sense before you really get going and start scaling up.
• Demanding business
  When you’re running a business, there’s a lot to do. Especially in those early stages you’ll find yourself wearing multiple hats and taking care of every aspect of your business all the way from operations to customer support to sales and marketing. You might find this a lot of work, and it’s hard to resist the temptation of putting more and more of yourself into your project at the expense of everything else.
• Answering to customers
  Even though you’re your own boss, that doesn’t mean you aren’t accountable—if you’re selling physical or digital products, you’re responsible for ensuring product delivery and quality, and taking care of your customers throughout their journey with your product. 

25 Careers Where You Can Be Your Own Boss

Spoiler alert: picking a new job, career, or niche where you can be your own boss is a huge part of the battle. But don't stress just yet - after giving you a few ideas of ways that you can work for yourself, we delve into 10 steps that you can take to be your own boss, including how to find your niche. With that in mind, let's get started with some solopreneur career inspiration.

1. Start an Online Shop

Building a successful online business is easier today than it ever has been, and if you’re the type of person that is able to put a finger on a market’s pulse and see gaps that need filling, consider ecommerce. The great thing is that you can sell anything online as long as there’s demand for it, from pet accessories and wedding-related items all the way to digital-only products. There are two main things you need to think about—finding a marketplace like Whop to sell your thing, and how to manufacture your product in sufficient quantity. Luckily, there are plenty of ways to source goods, which we’ll cover in the next entries on this list.

2. Dropshipping

Dropshipping is an ecommerce business model where you manage an online store without actually holding any physical inventory. When you take orders, you forward them directly to your partner wholesalers or manufacturers who handle most of the fulfillment by packing and shipping the goods directly to your customers. Your main responsibility as a dropshipper is to take care of marketing, sales, and customer support.

3. Print-on-Demand

Print on Demand (POD) is quite similar to dropshipping, except in this case you (or an artist you partner up with) work up some designs and then source both a manufacturer and a printer for your designs. There are plenty of firms that offer both of those services, and well-known platforms like Printful that you can use too. It’s a lot more involved as a business than dropshipping, but it can also be very satisfying since a successful POD business means that your creativity is being appreciated by lots of people.

• How to start a side business
• Small business statistics
• Start your business on Whop

4. Subscription Boxes

A subscription box is a clever model of ecommerce. Quite simply, you’re going to be repackaging curated goods in a certain niche—meaning, you put together a box of products that serve a customer’s needs, such as a week’s worth of exotic snacks or fitness products and supplements for a month. You then deliver this box by mail every month, and enjoy that lucrative subscription revenue as long as you keep customers signed on and the boxes rolling out. 

5. Retail Arbitrage

Arbitrage is the practice of buying a product cheaply on one market and selling it for a higher price on another market, and you can apply this to ecommerce too. By taking advantage of programs such as Amazon’s FBA, Walmart Plus and Facebook Marketplace, you may be able to establish consistently profitable retail arbitrage streams—check out this guide for the whole scoop.

6. Sell eBooks

Becoming an author is a lot easier than ever thanks to the internet and the advent of self-publishing. Getting your name in print used to be a matter of convincing a publisher to let you through the gate, but those days are no more. As long as you have some experience, expertise, or just a story to share, you can consider self-publishing and selling eBooks as a valid way to become your own boss.

7. Online Courses

This is a great one to tie together with eBooks if you’ve got valuable expertise in your corner. Courses are one of the best ways to pick up any skill, so by creating and selling a course you’re creating a product that is highly desirable in nature. Granted, there are plenty of courses out there on the internet, so you’ll have to differentiate yourself—the cream quickly rises to the top, so focus on delivering value, and pick a high-traffic marketplace like Whop to sell on.

8. YouTuber

You could actually create video content on just about any platform, but YouTube is the biggest so we’ll focus on it for now. It also has a straightforward route toward monetizing your content—all it takes to start earning on YouTube is a subscriber base of 1000 and 4000 hours of video watch time. These thresholds are very attainable if you pick your niche well and try to deliver quality content on a regular schedule. Again, there’s tons of video content in just about every imaginable niche, but if you pick something you’re passionate about there’s every chance you’ll succeed.

9. Podcaster

If you aren’t too confident with video content but like the idea of audio, then consider podcasting. It’s a fantastic way to go in-depth about a subject you’re close to, and the sky’s the limit—you could just as easily rock a monologue podcast about current events in a certain area as you could fit a mic to your table and record your gaming group, your mates having a chat about the weekend’s game, or discussing the latest scientific breakthroughs.

10. Streamer

If gaming is your thing, whether it’s the latest FPS, Minecraft, MMORPG or just about any genre or title imaginable, there may be a streamer somewhere in you. Just get on YouTube or Twitch, hook up your mic and camera, and start playing—all that remains is to get discovered. As it happens, you don’t just have to play games to stream; streaming is just a live version of a YouTube video for a lot of creators, and many use it like a soapbox or a stage where viewers can often be very generous with their tips.

#11. Blogger

This is a bit of an old-school form of content creation compared to the last few entries on this list, but it’s just as relevant now as it ever was—perhaps even more so. Blogs are often the best authority on a variety of subjects, although they might be a slow-burn when it comes to revenue. It can take a little time to build up a following and a reputation as a blogger, but once you reach that critical mass there’ll be no stopping you. 

12. Social Media Manager

If you’ve got a knack for social media, good news—you’re very much in the minority. Social media can be really difficult to juggle or even handle for entrepreneurs and larger businesses alike, so if you’ve got some skill in that area, your services will very much be in demand. It’s also one of the best ways to join the team of your favorite YouTuber or streamer. Once they make it to the big time, one of their first hires tends to be for a social media manager or curator.

13. Event Planner

Event management is another of those skills that is extremely difficult to find, so if you’ve got it, use it. Whether it’s planning private events like weddings or focusing more on the corporate sector, the event space is growing again post-lockdown. You’ll need to be organized and professional, and having contacts in the biz (such as catering and entertainment) helps, but this is an industry that you can establish yourself in quite quickly if you do it right.

14. Web Developer/Programmer

Programming and web development are extremely lucrative, but you don’t have to be a salaried Silicon Valley type to get in on the action. This is something you can do on a freelance or contract basis from wherever you are, so as long as you know your way around the right programming languages, you can dictate your own terms.

15. Graphic Artist

Despite the proliferation of sub-standard AI art, graphic artists are still in demand across a variety of industries. If you’ve got skill, you could hire yourself out to practically any industry—and that’s not even mentioning private commissions, which can be extraordinarily lucrative if you’re skilled in those high-demand styles.

16. Bookkeeper/Accountant

Just about every business needs someone to take care of its books, and while most larger companies have entire teams of accountants, plenty are happy to take on freelancers. How far you take it is up to you—simpler bookkeeping can be managed easily with the use of some simple software, but to take care of higher level accounts and ensure regulatory compliance you may need to get yourself certified.

17. Recruiter

Recruiting is an easier field to get into than accounting since most firms outsource a lot of their recruiting. This is something you can take advantage of as a freelance recruiter, and there’s a great opportunity to provide a high-value alternative to most recruiting agencies. This may be especially true if you have significant experience in a certain industry, since you’ll know better than most what companies really want from their hires.

18. Online Teaching/Tutoring

If you’re knowledgeable about a certain subject, you can translate that into an income very easily. There are plenty of learners out there, adults included, who are looking for good teachers in a variety of disciplines. Even good old English might be enough—professionals in countries all over the world are in the market for native English speakers to learn from on a variety of platforms.

19. Consultant

High levels of expertise or industry experience can be put to use in other areas, but if you’re a real expert, consider consulting. It might be worth looking into whether your current job is possible as a consultant, too—a little bit of market research will give you an idea of how many people can do what you do, and if your company would struggle to replace you, you might be able to turn your expertise into a consulting role.

20. Copywriter

Copywriting is one of those universal necessities today, and the text medium is close to unparalleled in importance. Just about every company needs copywriting services at one point or another, and you can take full advantage of your writing skills by becoming a copywriter.

21. Video Editor

Video editing is a little bit niche compared to copywriting, but it’s an incredibly difficult skill to acquire and is in very high demand in some areas thanks to its rarity. Becoming an efficient and creative video editor will give you a fast track into industries such as TV, and you can take on a variety of fun projects as a freelance video editor.

22. Financial Advisor

If you’ve watched practically any finance-related content on a platform like YouTube, you would have heard or seen the disclaimer “not financial advice”. Well, a financial advisor is actually allowed to give financial advice, and you can become one after picking up the relevant certification. You can work independently and take on clients, managing their wealth and portfolios, and growing your own.

23. Real Estate Agent

Real estate agents sometimes get a bad rep, but you can look at that as an opportunity. It’s a lucrative business to get into since the commissions can be outstanding, but you do need to be a bit of a people person. It’s very much an independent sort of job, though, and one that very much sees you being your own boss.

24. Real Estate Flipper

Staying in the real estate niche, flipping could be a very interesting business if you’re the sort of potential with an eye for potential and some experience around homes and maintenance. You’re going to be looking for run-down or distressed properties, buying them on the cheap and then fixing them up, adding value, and looking to sell for a much higher price. This one can be risky when you get going since you’ll either need a lot of capital or a big loan to get started, but after you make that first sale it gets a lot easier.

25. Landlord

This is another risky one since buying a property can be rough, especially given the uncertainty of bouncing interest rates and rampant inflation. However, everyone needs a roof over their head, and as a landlord you can enjoy the benefit of real estate assets on your books and rental income paying off your mortgages. If you can get your numbers right and approach this role with a sense of reason as well as respect for your tenants, you can snowball this business model with multiple properties.

10 Simple Steps to Be Your Own Boss

Now that we have looked at some ways in which you can be your own boss, let's unpack the important steps

Step #1: Take Stock of Your Situation

The first thing you need to do is sit down with a clear head and think about your own situation, as well as where you are with your life and career. Change is hard, and making the transition to freelancing or self-employment can entail plenty of upheaval, stress, and effort without immediate reward.

If you value the comfort and structure of your current job or simply don’t have the time or energy to start something new, you may want to hold off for now. Given the current economic climate, plenty of people are forced into a paycheck-to-paycheck existence. Becoming your own boss might be a way out, but you might have to devote all of your (limited) spare time to your new endeavor.

So, be honest with yourself and try to take an objective look at your situation and how much time and effort you have to work with. Do you have responsibilities that take precedence, such as children or elderly relatives? Do you have some savings to live off for a while if things don’t work out? 

Even if you come out of this exercise knowing that you have no savings and as little as a couple of hours a week that you can devote to your new business, you can count that as a positive—now you know what you’re working with, and you can plan your next steps accordingly. 

Step #2: Find Your Niche

This one’s easier said than done for a lot of people. Some folks are visionaries and seem to come up with million-dollar ideas all the time, but there are plenty out there who don’t have it quite as easy. It’s important to pick something that matches both your skillset and the restrictions (if any) from your personal situation.

Ultimately, the best way to find your niche is to do something that you’re passionate about. If nothing else, it’s a lot easier to find the drive and motivation to keep plugging away at a business if you have a genuine affinity for it.

You might end up being surprised about just how much of a market there is for something you may have previously considered a niche interest or hobby—just look at the number of people selling handicrafts online, for example, or streaming games, selling trading indicators, consulting, copywriting, film-making, deal-hunting, or even recording their tabletop adventures in podcast form.

Once you’ve found your niche, you’re well ahead of just about everyone else who’s sitting behind a desk dreaming of freedom. Sure, you might still be in that same stage, but the light at the end of the tunnel is suddenly very bright indeed.

If you’re still struggling to find your niche, check out this article on making money online. In it, we cover plenty of great online business models such as dropshipping, affiliate marketing, content creation, self-publishing, SaaS and more, so your niche might just be a click away.

Step #3: Plan, Plan, Plan

Now that you know what you want to do and what your limitations are, it’s time to plot a path forward. One of the most common pieces of advice given to entrepreneurs is to “just take the leap” - but it may not be quite as simple.

First of all, your approach will be very different based on how much in the way of time and resources you’ve got to sink into your new business. If you have a solid safety net and the freedom to just throw yourself into your new gig full-time, great—but if not, you might have to think about how you can do it as a side hustle while ensuring you’re still taking care of your other responsibilities.

Then, you’ve got to set some goals. It might take a while to monetize some side hustles, and there’ll be plenty of trial and error when it comes to getting things like your marketing mix right. If you want to be a content creator and start a side hustle as a YouTuber, it’ll take a while before you’ll even see a single cent of revenue. You’ll need time to fine-tune your craft and build an audience, and it could be months before you get your first sponsor—so plan for that, and don’t hand in your 2-week notice just yet if you can’t afford it.

Step #4: Lay the Groundwork

Once you’ve got your master plan in place and you have a good idea of how you’re going to build your new business, it’s time to start taking those first steps. Rather than just diving in, though, it’s better to take considered first steps—validating your business idea through market research, for example, can turn up some great insights that’ll set you on your way.

You’ve also got to get the basics down. Just because you start a social media channel doesn’t mean you’ll get any traction even if your content is good. This is where you need to learn a little bit about SEO (search engine optimization) in order to generate impressions, and then figure out how you can turn those impressions into views, and views into engagement.

What about a more traditional business or ecommerce? Well, you’re still going to have to develop your funnel at this stage—start with identifying your ideal customers or target market, then develop the right channels to get them to notice you. Once you’ve gotten that impression, then it’s about driving traffic to your site or landing page, and then directing the customer to your CTA (call to action) or checkout button.

Step #5: Establish Your Infrastructure

We did mention landing pages there, and that’s just one small element of what you’ll need to set up your business. Imagine starting a shop—not only will you need the products, but you’ll also need some real estate in a good location, some paint on the walls, shelves for the product, and a cash register if not a fully functional EFTPOS system.

This analogy holds even if you’re running an online business of some kind. In the place of a physical store you’re looking at a website, and instead of that cash register you’ll need to integrate with a payment network. Then there’s the option of putting your store on a larger ecommerce marketplace (the equivalent of renting store space in a high-traffic mall) and so on.

You’ll also need to think about things like your company’s legal structure. By just getting started with a side hustle you’re basically a sole proprietorship, but moving into an alternate structure like an LLC (or setting out a path to doing so in the future) can be a smart business move.

So, don’t forget to put some time into getting all of these elements in place. Whether it’s signing up with a vendor for dropshipping or downloading and learning recording and editing software for content creation, there will be different aspects of your business or tech stack you’ll want to nail down at this stage. 

Step #6: Bring on Partners

If step #5 sounds intimidating to you, don’t worry. As your own boss, it’s totally up to you how much of the work you do yourself, and how much you try and hand off. Hand off to whom, you ask? Well, you don’t have to do all of this alone if you don’t want to.

A lot of successful entrepreneurs link up with partners who offer complementary skills or other benefits, but that’s not all we mean. Especially for online businesses, you have a vast variety of choices when it comes to integrations or partnerships that can help you out.

For instance, listing your online store on Whop will take care of a lot of what you might be worried about. Discoverability and a wide audience? Check. Payment integrations? Check. Easy-to-customize store page built for you? Check. Customer service? Check. So, if you’d prefer to devote as much of your time and energy on perfecting your product or service, look for a partner like Whop who’ll take care of everything else for you while truly letting you be your own boss.

Step #7: Develop Your Brand Identity

As you get the ball rolling with your new business or side hustle, it’s important to focus on being yourself and settling into your own niche. You can study and learn from what the other successful businesses in the industry are doing, but you’ll find that developing a strong identity or style will serve you well.

To put it simply, establishing and then staying true to your own brand identity will help you to develop a customer base. A customer who likes your product or a viewer who likes your content will come back, but you might turn them off if you change your style too often and too dramatically. So, keep giving them what they’re coming back from, and use their input strategically to improve your offering as you go.

Step #8: Scale Up and Optimize

As your business starts to grow, it’s important to maintain a strategic overview and keep an eye on where your time and effort is going. Analytics will serve you well at this stage, especially if you’re transitioning your focus from growth to retention. If you’re in ecommerce, start paying attention to metrics and KPIs, and figure out which ones you need to improve to keep your business on a sustainable trajectory.

Many entrepreneurs fail because they aren’t able to shift their focus and view their business with a wider lens at this stage, so don’t fall into that trap. Keep your customers coming back and make sure to provide solid customer support if it’s applicable. You might also look into how partners like Whop can help you cross-sell and upsell, increasing your gain per customer.

Start outsourcing elements of your business you feel that you can in a comfortable manner—if you’re a monetized YouTuber at this stage, for example, it might be worth looking at the freelance market to get your video editing done.

Step #9: Delegate and Automate

It’s an electric feeling to have bigger and bigger checks coming in every month, but it’s worth reminding yourself of step #1—there may be personal circumstances or dependencies that you need to prioritize, even though it may be tempting to sink deeper and deeper into your business.

The point here is that being your own boss also means that becoming someone else’s boss might become an option before too long. You might consider hiring an employee or three rather than looking into the gig market, for instance, or invest in SaaS or other productivity-enhancing premiums—your time is getting more and more valuable, so at this stage it may make sense to pay in order to lighten your workload.

If you’re a content creator, this could mean a full-time editor or camera crew, or even a social media manager and stream moderator. If you’re in e-commerce, think about administration and accounting support, or a marketing and sales team. Pick and choose which tasks make most sense to continue doing, and which tasks you can comfortably offload. 

Step #10: Rinse and Repeat

That’s it, right? You’re your own boss now, you’re leading a team of employees, and you’re running a business that you’ve built from the ground up and are passionate about. It keeps you going, and helps you to meet your financial goals. As long as you’re able to keep on top of market trends and make the strategic decisions you need to keep your business sustainable over the long term, there’s nothing stopping you.

That being said, it’s very possible that you’ve caught the eye of a bigger corporation for an acquisition by this point. You might find yourself considering selling your business for a number with a lot of zeroes behind it, but beware—especially if you’re the “face” of your business, a potential buyer may attempt to stipulate that you remain full-time with the business post-acquisition. As you might imagine, this means no longer being your own boss, and a lack of autonomy and control that may be an extremely difficult pill to swallow given that, on an emotional level, this is still “your” business.

So, if you want to continue being your own boss but also sell your business, then make sure you aren’t locked in. It might be tough to let go of something you’ve put heart and soul into building, but look on the bright side—you might be coming away with millions in seed capital for your next venture.

Traits You Need to Be Your Own Boss

By now you're probably excited by the idea of being your own boss, and while this is a great idea and can be extremely rewarding once you make it work, it isn’t for everyone. Let’s take a look at a handful of traits you may need or consider cultivating if you want to embark upon your entrepreneurial journey:

• Discipline
  One of the best things about being your own boss is the fact that you can dictate your own schedules and workload. The problem here is that a lot of people can’t quite handle this—procrastination is a trap that many fall into, and on the other side of the spectrum, some people just can’t say no. You need to be able to set your limits, take breaks when you need them and refuse work if need be, but also have the ability to motivate yourself and get stuff done.
• Perseverance
  Being your own boss is great, but you need to work to make that happen. As we’ve detailed, a lot of this work will be difficult, lonely, and may not even pay dividends for a while. You need to be able to keep plugging away until you hit your goals, though again, be disciplined about it. Almost every successful entrepreneur has a bunch of failures and lessons learned behind them.
• Organization
  The function of a boss, generally, is to organize a team or a department. As your own boss, this task falls to you—and it can be a challenge. One of the most important things you need to learn is how to prioritize, taking care of things exactly as and when they need doing. You don’t want to get lost in the minutiae while the important stuff sits in your backlog.
• Empathy
  Your previous boss's lacking this might be why you’re here, and we can sympathize. It’s probably easier to be successful in business if you’re a stone-cold sociopath, but we’ll argue that empathy is far more valuable—especially when running a small or growing business, you’ll get far more repeat customers and far more productive partners or employees if you are able to listen, empathize, and actively try to be the sort of boss you always wanted.

Let Whop Help You Be Your Own Boss

Being your own boss is an extremely rewarding situation to be in since it means that you’re in charge of a business that you’ve built, likely from the ground up, and are now enjoying the fruits of all that labor. With the hard yards behind you, you can finally put your feet up and truly enjoy what life has to offer with the freedom of knowing that, not only have you taken care of your loved ones, but whether you even work tomorrow is one person’s decision—your own. Whop can help you make this dream a reality, serving as your partner in business.

👉 List your business on Whop today—whether you’re selling courses or software, mentoring people or looking to manage memberships for your content subscribers, Whop can take care of your customers, facilitate payments, make you more discoverable, and optimize every facet of your business. Sign up with Whop today.