12 Pros and Cons of Working for Yourself

October 20, 2022

12 Pros and Cons of Working for Yourself Over the past few months, we have been talking about all sorts of Second Acts. From completely changing career paths to starting your own business. Today, we want to focus on the rewards and drawbacks of starting your own business and working for yourself. The pros and […]

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The Second Act Success Career Blog features articles to help inspire you as you navigate your career journey. Plus, you'll find show notes from podcast guests who have shared second act success stories. My hope is that these quick reads will offer advice and comfort knowing you are not alone on your path towards second act success. xo - Shannon


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12 Pros and Cons of Working for Yourself

pros and cons of working for yourself

Over the past few months, we have been talking about all sorts of Second Acts. From completely changing career paths to starting your own business. Today, we want to focus on the rewards and drawbacks of starting your own business and working for yourself. The pros and cons of working for yourself are plentiful, but with nearly 10 million people in the US self-employed in 2022, according to the US Bureau of Labor & Statistics, it is worth considering. 

There are myriad industries and pathways to explore if you are interested in working for yourself. You can focus on a specific skill you have, such as baking, accounting, gardening, painting, writing – the list goes on. Many people leverage the skills they have developed over their career to launch their own related business. Others go all-in on their hobby, opening a catering service, etsy shop or photography business.

But even if you don’t have specific skills, you can still find a way to work for yourself. Opening a franchise or buying an existing business can be great opportunities. Taking on work that others don’t want to do or don’t have time to do, like cleaning, organizing, child care, walking dogs, courier service, and virtual assistants can also be highly in demand.

No matter what type of self-employment you are seeking, you need to go into it knowing all of the pros and cons of working for yourself. 


Benefits of Working for Yourself

Freedom and Flexibility

Being your own boss allows you to schedule your time in a way that works best for you. No more asking permission for a day off or to make a doctor’s appointment. If you want to coach your kid’s sports team, you can schedule your day around it. 


Set Your Own Pace

You can scale up or down as much as you need, based on your comfort level and your budget. If you are unsure about certain areas of the business, you can move slowly, easing your way in. If you have the time and energy (and confidence…and budget), you can race ahead. Regardless, you are in charge and get to set the pace for your business. 


Pride and Job Satisfaction

Choosing how and where you spend your time goes a long way towards overall job satisfaction. Knowing that you built something from your own brain and effort engenders a sense of pride that building upon someone else’s ideas can’t match. Being able to look at what you have accomplished at the end of the day or year and know that it was your baby is truly an awesome feeling. 


A Boss You Like

Just an assumption here, but when you work for yourself, at the very least you are going to agree with all the decisions and direction of the company. Second-guessing and micromanaging is gone. As a self-employed person, you are the start and end of all decisions, be them strategic, creative, or otherwise. 


Set a New Standard

If you thrive in a more formal, scheduled environment – Great! If you prefer to work in your comfiest clothes, it’s up to you. Hard deadlines, hours, pacing, hustle…all of these can be modified to what works best for you AND how you work best. 


In Control 

The reins are in your hands. You decide which projects or clients you take on, how much you charge. If you want to travel or work in an office. Do you want to hire employees, or freelancers and consultants, or just go it alone. You can decide whether you want to work on a lot of little clients or a few larger customers. Do you want be an online business or need a retail space. All of the decisions, big and small, are yours to make. You can shape the company or working environment around your preferences. 


Drawbacks of Being Self-Employed

Insurance and Benefits

Becoming self-employed comes with a lot of risks. Not least of them is forgoing any corporate provided benefits, like subsidized insurance, 401Ks, or any other benefits typical of large and small companies. Working for yourself means private insurance. You need to manage your own retirement savings plans. Group discounts and other soft benefits are history. 


The Hustle is Real

Starting a new business is tough. Your personal drive and ambition are only a part of the battle. Depending on what type of self-employment you are considering, you may be faced with constantly hustling and searching for new clients/customers. Whether you are a freelance writer, a graphic designer or a dog groomer, you need to always be hustling. Marketing yourself, cold calling, reaching out to your network, upselling, incentivizing, the list goes on. If you are not getting new business, you are not making any money. If you are not someone who is self-motivated, this could be a very tricky pursuit.


How About The Hours? 

While working for yourself can seem like a dream on the outside, the reality is a little more daunting. Yes, you can usually set your own schedule. But the truth is, most successfully self-employed people have said goodbye to the M-F, 9-5 schedule. You work until the job is done. That may be 10pm. It may be every Saturday and Sunday. It may be every spare moment that you have. 


No Such Thing as a Sick Day

If you don’t work, you don’t get paid. There are no sick days. No vacation days. No one will cover for you if you want to go away for a week. It is your business and you need to make sure that it is running, whether you are actively working or not. If you are running a serious business, you can’t afford for customer service requests to be ignored because you are in Disney World. If you miss a deadline because you have the flu, your clients may walk or demand a refund. 



Being self-employed comes with a lot of pressure. All decisions go through you. Whether you have employees or work alone, you need to take on multiple roles. HR, marketing, accounting, customer service, sales, strategy, web development, sourcing, distribution…all need to be handled IN ADDITION to whatever your actual job entails. To run a business properly, not just a hobby, you need to be buttoned down and simultaneously working on all of these areas. Often these activities end up happening after hours. 

You may have taken out some loans or borrowed money from friends or family to get started. Plus, there is no guaranteed paycheck. If you are the sole income in your household, this is assuming a ton of pressure to get this right. 



Anyone can start their own business. However, mustering the courage to take the first (and next) step can feel impossible. Building your own self-confidence, taking out scary loans, marketing yourself – these can all feel intimidating and daunting. While you may be working alone, starting your own business often relies on the support of others. Whether it’s mentors, parents, friends or partners, overcoming these initial obstacles can often become a team effort. 


Truly, the most important step in starting to work for yourself is believing in yourself. There are countless pros and cons for self-employment, but they all start with you. Talk to a mentor. Hire a coach like Shannon to help you get started. Consult with your network. Start as small as you would like and go from there. Working for yourself brings freedom. Use that freedom to make a working life that works for you.