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Want to work for yourself? — pros, cons + tips for deciding your next step

Table of ContentsUpdated Sep 11, 2018

“I want to work for myself.” It’s probably something you’ve repeated to yourself as you’re sitting at work, watching the clock, waiting for the little hand to hit 5.

So many dream of it — but don’t act on it. Instead, you waste years of your career working for someone else settling for mediocrity.

While it sounds like a perfect situation, working for yourself is not for everyone. If you’re in the stage of deciding whether it’s for you or not, this article should help you in making that decision.

I want to work for myself: why you shouldn’t do it

When you think about working for yourself, the first thing that comes to mind is an idealistic fantasy.

The idea of no boss to answer to, working the hours you choose, and doing things your way may all be part of working for yourself, but you can’t only think of the positives. When making such a big decision you must also think of the negatives.

I want to work for myself, but I need a stable income

A traditional 9 to 5 job where you clock in and clock out provides you with a steady income that you can count on. When you work for yourself, there is no guarantee of when or where your next check will be coming from, especially when you’re first starting out.

To create a stable income, you have to have a steady flow of work coming in. Depending on what type of work you do, the task of getting new clients can be a job on its own.

I want to work for myself, but I don’t have the time to invest

Working for yourself and starting your own business is one in the same. A business needs your time, and a lot of it at that. In the early stages of working for yourself, the time you have to invest is crucial. If you aren’t willing to put in the time, don’t even think about working for yourself.

I want to work for myself, but I thrive on social interaction

Something that you might not think about when you decide, “I want to work for myself,” is that most likely that also means by yourself. Although you may not always be keen on the people you work with, working alone can be worse.

The isolation that come with working for yourself can be quite detrimental if you are not careful.

I want to work for myself, but I’m not good at wearing multiple hats

No matter what type or size of business you have, they all require several departments. Even if you are working for yourself, those other “departments” still must exist.

Let’s say you are a graphic designer who has decided to quit your agency job and work for yourself. You now have gone from just a designer to the added hats of: bookkeeper, marketing manager, social media director, customer service representative, and on and on.

If you can’t handle multiple roles, you should re-think the whole “I want to work for myself” thing.

I want to work for myself: benefits for going solo

When your long, dreadful days at work become muddled into a blur and you’re only counting down the days until the weekend, then this is a sign you need change.

Even though working for yourself isn’t for everyone, there’s plenty of positives that come along with it. If you’re committed to putting in the effort, here’s some benefits to working for yourself.

Working for your own gain, not someone else’s

At essentially any job as an employee, you are putting in 40+ hours a week, exhausting yourself for someone else’s gain. All your talents and knowledge are being used for growing a company that isn’t yours. Why not use your expertise to grow your own business?

Control your own destiny

Looking for a boost in your income? When you work for yourself, you have the ability to put in those extra hours to gain that added client or work. It takes more effort — but it’s there if you want it.

On the contrary, if you’re overloaded and feeling burned out, you could just say no to a couple projects to free up your schedule how you want it.

Do what you love

You might get comfortable at a job because it’s easy and convenient. You show up, do what you’re told, and collect the paychecks. There’s so much more to life, though.

When you work for yourself, you get to choose what you do, therefore (hopefully) making it more enjoyable. You’ll start looking forward to work, and enjoying the perks that come with working for yourself.

Flexibility & freedom

When you work for yourself, you make the rules. Whether you’ve been wanting to go on that 2-week vacation, or just have family coming to visit — you have the luxury of creating the schedule you want. Sure, the downfall to that is you don’t get paid vacation, but that’s what a little bit of OT is for.

I want to work for myself: checklist to determine if it’s right for you

If you’re looking to make that jump into working for yourself, there are some characteristics to look for in yourself.

Being a solopreneur takes a lot of courage, drive, and dedication. If you feel that you meet most of the checklist below, then working for yourself is probably not a bad idea for you.

You’re able to check your ego

If you think working for yourself is going to boost your ego, think again.

The reality is, if you lead with a big ego, you’re most likely going to be your own worst enemy. People are not going to want to work with you so it’s best to check your ego at the door if you are thinking, “I want to work for myself.”

You’re a problem-solver

With all the new hats that you will be wearing as a soloprenuer, the more problems you will face on your own. Being a good problem solver is a key to success that you must possess.

You’re money-smart

This could be the single most important item that you can check off when wanting to work for yourself. If you fail in this, not only will your business fail, but if you are not prepared, your home and family life may take a hit as well.

You definitely DO NOT want to take this lightly. Determine your monthly expenses and evaluate your financials on a regular basis. You must be smart with your finances!

A good tip before when you are at the “I want to work for myself” stage is to seek the advice of a financial advisor to, at minimum, help educate you.

You have the willingness to work for it

It’s not going to come easy so you must have the time, patience, and determination to stick it out. The ebbs and flows of working for yourself aren’t for the weak, so you’ve got to be strong and consistent.

You don’t do well with structure

Getting to work at a specific time. Reporting to your boss. Doing what you’re told. This kind of work day structure can be boring, redundant, and tedious. If this describes you and you can’t stand it, then working for yourself is probably the solution.

You’re self-motivated

You want to ditch your boss to work for yourself, but can you actually get work done without them? If the answer is yes and you have self-discipline, then you are one step closer to working for yourself.

Keep in mind that it’s not as easy as it sounds. Working on your own does give you flexibility, but it also gives you a million more distractions to push through.

You feel you have more to give

Sometimes in your workplace you’ll find that you’re confined and limited with your ideas.

Maybe you have a really awesome social media campaign idea, but it doesn’t align with the company brand, so you have to hold back. Or maybe your boss is incredibly particular and doesn’t like accepting new ideas.

When you work for yourself, the only one holding you back is yourself. Use those awesome ideas you’ve held onto and put them to use.

I want to work for myself: what to consider before you ditch your day job

Before you go putting in your two week notice, there are things you should definitely think about first. Being prepared, both financially and mentally, is crucial to starting out your business with success. I suggest you take the following into strong consideration before you start working for yourself.

Test your business on the side

Before you go leave your job, you’ve got to test your business idea. Otherwise, how will you know it’s going to work?

Start spending some of your evenings and weekends brainstorming your business. Once you have an idea, put some feelers out there to close friends and family and begin testing the business. You may find that nobody takes to it, at which point you should take a step back and reevaluate.

This phase is incredibly useful, because you’re able to test your idea and make adjustments/tweaks as you go, all while still bringing in your full-time paycheck. So I recommend giving your business a test for at least 1 year to see whether it’s something you can fully rely on as your main source of income (and if you enjoy it, too).

Have a nest egg built up

When you first start working for yourself, there may be a good amount of expenses upfront (depending on your business).

For example, say you’re a freelance writer, some costs may include: a website, logo, business cards, a computer, and more. These alone could cost you upwards of $3,000+.

Additionally, when you first start working for yourself, you may not have the income to match your previous full-time job. So you’re going to need some money saved up to fill in the gaps while you build your business.


A perk to a full-time job is having health insurance. Well, when you work for yourself you’re on your own. Insurance can be expensive, and if you eventually have employees it could become an even bigger expense.

Do the research to determine how much this can cost you and build it into your business expenses.


As a self-employed business owner, you will definitely want to consider creating (or adding to, if you already have one) a retirement account. There are several different types of retirement accounts, including a 401K, IRA, Roth IRA, and more.

Exploring your options early on will help you in the long run, but again — this is money out of your pocket. Coming up with a savings plan can be useful for staying on track and knowing what to expect each month.


Compared to having a regular 9-to-5 job, filing your yearly taxes are an entirely different beast.

Throughout the year, it’s paramount that you track all your expenses and income, keep your receipts, and stay organized as possible. If you do that, it’ll become even easier come tax time.

To further make yourself feel at ease, hiring a local accountant can be extremely beneficial. They’ll walk you through what you need to do to make tax season as painless as possible.

I want to work for myself: what to expect

As we’ve covered already, working for yourself is not always going to be easy. In fact, I can guarantee you it won’t be easy. No matter how much you set yourself up for success, you’ll constantly encounter bumps in the road. But the more you know, the better suited you’ll be for tackling those obstacles head on.

It will be a rollercoaster of a ride

Sit back, and enjoy the ride that is solopreneurship. It’s ups, it’s downs, it’s loops, and everything in-between, there’ll be no shortage of excitement and struggles. Building your own business is not for the faint of heart.

Not easy, but extremely rewarding

As a business owner myself, one of the biggest positives to working for yourself is the amount of pride I feel in my work. When I get the positive feedback from a client, it’s incredibly rewarding and gives me the fuel to continue to improve.

You’ll constantly be learning

There’s no doubt that when you work for yourself you are always going to run into obstacles. No matter how many books you read, or podcasts you listen to for advice on how to work for yourself, there will always be lessons learned along the way. However, this only will make you a stronger, and more well-rounded businessperson moving forward.

I want to work for myself: the essentials you’ll need starting out

When you first start out, there are some basic essentials you’ll have to strongly consider for your business. Here’s some suggestions on the basics for establishing your new venture.

Business name

Establishing your business name is a pretty crucial first step when you start to work for yourself. Whether you choose to just go by your name, or a clever thought-up business name, always make sure that 1) it’s relevant to your business, and 2) it’s memorable.

For tips on naming your business, read this article.

Business license

In most instances, even if you are working for yourself out of your own home, you are required to obtain a business license. This may be a city business license, or even a county business license (and sometimes both).

For more information on business licenses, you can read more here.

Business plan

Creating a solid business plan before launching your idea is important for deciding your main objectives and goals. When you work for yourself, having a structured plan in place will keep you focused on your goals.

Learn more about how to create a business plan here.

Business cards

No matter how dated business cards may be, they are the easiest and quickest way to provide someone with your business information. Not only that, but you can use your business cards to make a statement. Use a bold design, include a special discount code, or make them a funky shape — they’ll be sure to remember you by what you did different.

Accounting software

Whether it’s signing up for Bench or utilizing a simple Excel spreadsheet, you’ll need some sort of way to track your income and expenses. Here’s some additional websites that are great for helping track your financials: Xero, Quickbooks.

Invoicing software

The key to a successful business when you work for yourself is, of course, making money. Well, you can’t make any money if you don’t send invoices to your clients.

There are many options out there to choose from, like Freshbooks, Bonsai and AndCo. You can also choose to put one together yourself in Word or InDesign and export as a PDF. Either way, it goes without saying that you’ll need to send invoices in order to get paid.


Having an online presence for your business, no matter what type of business it may be, is absolutely necessary. If you’re more into DIY, you can explore the website builders such as Squarespace and Wix. Having something online that you can point potential clients to helps with your credibility and get discovered.

For our complete list of our top tools for working for yourself, check it out here.

10 jobs to find success in working for yourself

There are many jobs and industries that allow for individuals to find success on their own. Below is just some of the top jobs of to consider when you want to work for yourself.

Social media consultant

It’s no surprise that social media jobs continue to be on the rise. Almost every company has a social media presence and it’s only continuing to grow, therefore always having a need for social media content and strategy. So we can count on this to stay relevant for quite some time.


Driving for these companies has quickly gone from earning some money on the side to a full-time job for many. You can make your own hours, use your own car, and not be confined to a cubicle.


If you have expertise in anything from math and writing, to the piano or guitar, being a tutor is always going to rank as one of the most popular jobs when you want to work for yourself. Making your own schedule, meeting new people, and doing what you love are just some of the benefits.


For those who are good at the written word and are passionate about it should have no problems when it comes to finding success. There are so many different opportunities including copywriting, blogging, and journalism.

Web Designer

As long as the internet exists there will be a need for web designers. The most difficult part of this field, like many, is finding new clients, although the technical expertise needed to build websites gives great potential for supporting a full-time income on it’s own.

Life/Career coach

Everyone could use a little, or a lot, of inspiration every now and then. If you’re really outgoing, inspirational, and into helping others improve, then this could be a perfect career for you.

Real estate

Real estate lets those who are social still be social despite working for yourself. It is very flexible with setting your own schedule, allows you to mingle with new people, and can be extremely rewarding when you make a sale.

Event planner

Another social job on the list is event planner. Although you may work for yourself, event planners have to work very closely with the clients and vendors. In this business, you get to express your creativity and watch it come to life.

Interior designer

Creative jobs tend to be popular among the work for yourself group. Interior designers also get to be social, explore their creative minds, and not be stuck in the office 24/7.


The options are endless these days. With websites and apps like eBay, Etsy, and OfferUp, it’s easy to become a seller. E-commerce is a great option when working for yourself.

Now it’s your turn

We’ve covered everything you need to know and think about when you want to work for yourself. Now, you’ve got to decide, is it for you?

If you’re still saying “I want to work for myself” at the end of this, then I wish you good luck and great success!

Comment below with your best advice for someone just starting out.

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Written by Adam Wright


Adam Wright is the Content Manager at Millo, in addition to running his own graphic and web design business, Adam Wright Design. When he's not working on his business, you can find him watching hockey or just about any type of racing.

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Reviewed & edited by Preston Lee, Editor at Millo.

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