How to be your own boss

This thought creeps up on everyone with a steady job now and then. You crave something besides the 9-to-5, something that doesn’t involve answering to a higher-up or checking in each time you want to stray from a predetermined process or operational goal. Have you ever wondered how to be your own boss? It’s got to be better than what you’re currently doing, right? 

Yes and no. Self-employment can be a wonderful step to finding a fulfilling career, but it’s also not as easy as just setting out and deciding to change the world through your particular product or service. We’ve put together some strategies to guide you as you make this shift.

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Advantages of being your own boss

There are many advantages of being your own boss – but there are also plenty of disadvantages. Let’s start with the good:

You control your hours

Flexible hours are likely a big draw if you’re looking to be your own boss. For parents, those nearing retirement and anyone who feels stifled by a 9-to-5, the ability to work when you want is the true definition of freedom. Want to surf in the morning? More of a night owl? When you are your own boss, you can live the life you want.

You control your earnings

Forget asking for a raise. As your own boss, all you have to do is raise your standards – and there’s no limit to what you can make. Your employer won’t limit your salary based on the market, industry or what others are being paid. And you keep every last cent of profit for yourself.

You control the decisions

We’ve all had to deal with a micromanager or a toxic coworker at some point. Being your own boss means no more people telling you what to do. No more managers to “consult.” No more coworkers questioning you. Bonus: When you’re responsible for the decision-making, that also means you get the credit for every achievement. 

Downsides of being your own boss

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Sounds great, right? Before you take the leap, understand that the total control that is the greatest advantage of being your own boss also has downsides:

No steady paycheck or benefits

This is the biggest drawback of being your own boss. If a big contract ends, a client takes your work in-house or there’s an economic recession that reduces demand, you could lose work. You also won’t have employer-subsidized health insurance or 401K benefits. You’ll need strategies for dealing with this uncertainty before it causes you stress.

You have to do everything

To be your own boss, you don’t just control the decisions – you have to execute on them as well. Networking, marketing, building a portfolio or website, getting on social media, staying ahead of industry trends, buying materials and paying bills will all fall to you.

It’s hard work

All of those tasks just listed? They don’t pay. You need to take into account these administrative tasks, as well as lack of benefits, when you calculate how much you need to earn – and how much you need to work. And you’ll always need to be “on:” looking for new opportunities and making connections everywhere. Make sure you have the drive to put in the work. 

What careers can you be your own boss?

You can turn nearly any skill set into a career where you can be your own boss. The best candidates are jobs that already have somewhat flexible timelines and that can be done from home. Here are some options to consider:

  • Freelance writer
  • Marketing consultant
  • Baker
  • Personal chef
  • Graphic artist
  • Website designer
  • In-home child care
  • Photographer
  • Life, business or health coach
  • Pet sitter
  • Real estate agent
  • Party or wedding planner
  • Personal trainer

Whether you want to work independently or recruit a team, there are hundreds of jobs where you can be your own boss. You’re only limited by your imagination and willingness to put in the work.

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Tips for how to become your own boss

Making the jump into entrepreneurship is a bold decision. If you’ve spent most of your life working for others, you have likely been insulated from many aspects of running a business. But to be your own boss, you’ll need to be the one coming up with solutions – and taking the blame. Learning how to be your own boss is a process of trial and error and requires deep belief in yourself and your vision. Use these tips to adopt a winning mindset right out of the gate. 

1. Realize that you are the CEO of your life

According to marketing guru Jay Abraham, seeing yourself as the CEO of your own life is one of the best ways to take control and become 100% accountable for where your decisions lead you. You don’t need to be your own boss to act as the CEO of your life, but you may want to be after you see the enormous benefits of taking proactive control of creating a meaningful existence.

Venturing into entrepreneurship makes you the top dog, chief visionary, master strategist, ultimate decision-maker and ace of accountability. This is a tall order, but a necessary one; once you break free from the daily grind of working for someone else, every element of your business and your life is in your hands. It’s up to you to decide what you can achieve and what you want and need.

If you don’t have the dedication and drive to see it through, it won’t happen. This type of mindset will help you strengthen critical leadership skills in every area of your life and leads many to strike out on their own so they can exert even greater control over their destinies.

2. Combine your passion and your skills

To discover how to become your own boss successfully, you must unlock your passion and your skill set, then combine them into a winning business idea. If entrepreneurship appeals to you but you aren’t entirely sure where to apply your talents, think about your top skills and your experience. Most of all, think about past jobs you found fulfilling. 

Still not sure what it takes to be your own boss? Look into what fields are particularly rewarding for the self-employed, and let others who have taken this path before you provide guidance along the way.

3. Figure out your finances

Before you learn how to be your own boss, you have to know how much money it will take to live on and build your business. Though money may not actually buy happiness, having enough to be comfortable is one of the keys to relieving stress and having an overall positive state of well-being.  

What are your monthly living expenses? How much do you intend to spend on equipment or other necessities? What sort of marketing plan do you have in mind as you scale your business, and how much are you willing to spend on that? How much do you need in the bank before you feel comfortable going all-in with your new venture? How will you know when it’s time to quit your day job?  

Don’t resign your current position in a moment of passion only to find out that you need the money. Keeping your side venture while you slowly scale up relieves pressure and helps provide financial support while you figure out how to turn your passion into profit. You’ll end up working some nights and weekends to build your business, but it will be worth it.

4. Invest, invest, invest

tips on how to be your own boss

Learning about investing is an essential part of planning to be your own boss. Tony Robbins has said investing is the most important financial advice he can provide to the self-employed. “Take advantage of the power of compounding,” he suggests, and let one small investment grow into a money machine over time. This money continues to accrue on the side, no matter what you’re doing; it can be your Dream Bucket money, your retirement and your emergency fund all at once. It can also help you achieve financial freedom so you no longer have to work a day job to fund your ideal lifestyle.

You aren’t limited to investing in the financial arena, either. Being your own boss means constantly investing in yourself. Enroll in classes, read books about leadership and keep track of new developments in your industry. Create a personal growth plan that addresses career advancement as well as enhances your relationships. The more you invest in yourself, the more likely it is your clients will invest in you.

5. Build your foundation

Begin putting the infrastructure in place so you are ready to commit full-time when the time is right. Research potential networking groups, such as mastermind groups, professional clubs or events like Tony Robbins’ Business Mastery. Find a mentor who can help you develop your skills and connect you with the right people. Use the power of proximity to elevate yourself in every possible way. You’ll also need to figure out where your permanent office space will be and make sure you have all the equipment needed, including hardware and software, to turn your side-gig into a career.

man showing how to be your own boss

Before you take the leap, create a loyal customer base. Your mentor or mastermind group can help you find the right customers. Make sure you diversify: much like diversifying your financial portfolio, diversifying your freelance projects prevents you from being dependent on any one client. It’s comforting to have one large, well-paying client that you know you can rely on – but if you devote the bulk of your time and energy to them, what will happen if they abruptly struggle financially or stop using your services? You’ll be cut off from that steady income stream you’ve been cultivating, which, in this scenario, is no different from losing a steady job. 

Depending on your schedule, set aside a few hours at least every other week and devote that time to finding new customers and clients. That way, one client’s disaster won’t necessarily mean disaster for you – and as an added bonus, you’ll likely diversify your skill set, too.

6. Keep your portfolio updated

advice on how to be your own boss

Figuring out how to be your own boss means learning how to market yourself, and there is no better way to show off your skill set than by providing examples of work you’ve already completed. You need a record of what you provide, whether you’re a landscaper, a plumber or a freelance writer, and you need to be able to get this information to potential clients quickly. An easy-to-navigate website with specialty areas highlighted will usually suffice.

How often you update your website or portfolio depends on how busy you are and how much client turnover you have, but aim to look it over at least once every three months and continually add examples of new projects you’re especially proud of.

If you’re pushing through a large number of new projects, you may even want to update it once a month to make sure potential clients see your newest capabilities. Always post new blogs and articles on your site. When it comes to how to be your own boss, success is heavily influenced by what you publish.

If you don’t have strong design skills, work with a website designer who can do the work for you so your site is professional and effectively conveys your brand identity. Many of your prospects will look at your website before they ever contact you personally, so it needs to make a good impression.

7. Turn your vision into action

Whether you’re working independently as a freelancer or want to become the next Steve Jobs, creating a powerful vision is vital to staying energized to work toward your goals. Connect your vision back to your purpose in life: How will your new business inspire you to make your life a masterpiece? What do you want to achieve beyond learning how to become your own boss? See the bigger picture: financial freedom. The ability to do what you want, when you want, as much as you want. A clear vision will give you strength to keep going when times get tough – and allow you to inspire others to follow you.

learning to be your own boss

You’ll also use your vision to create your business map. This is different from a plan: A business plan is a definitive way to get from point A to point B. A business map is a holistic and flexible view of your business that will tell you what’s working, what’s not working and how you can adapt. At Business Mastery, you’ll learn the right questions to ask to create a business map and use it to propel you to success in any economy.

8. Put your clients first


Being your own boss means putting your clients ahead of yourself. Take pride in your product or service, and make sure it’s something that creates value for others. But don’t fall in love with it – because the more you love it, the less willing you will be to make changes.

You are ultimately answering to your clients; they’re the ones you are working for, and they’re the ones you need to keep happy. Once you realize your customers’ lives are at the heart of your business, you’ll understand that their needs come first. If they want changes in what you produce, you need to listen to them and implement these changes.

Being your own boss means you are on the hook for producing the work and keeping up with changes in your field. Are your nearest competitors doing something different and offering greater value to your clients? Committing to constant and strategic innovation is one of the keys when learning how to be your own boss. You better adjust your practices or even your most loyal clients will leave you for someone else.

9. Learn to control your emotions

Selecting the clients and the projects you find interesting is one of the advantages of being your own boss, but it comes at the cost of a regular paycheck. Depending on what you arrange with your clients, you may be paid every two weeks; it might be every month or at the successful end of every project. There will be times when you’re flooded with work and flush with cash and there will be other times when the gigs and the money dry up and you’re looking for just about anything to bring in some income.

You’ll have potential clients tear apart your work or decline to work with you at all, but you’ll also have those who sing your praises and make you feel on top of the world. When you commit to the adventure of how to become your own boss, you have to accept there will be days when you long for the security of the day job even if you are pursuing your passion.

do not quit

A key to entrepreneurship is taking charge of your emotions. You’ll need strength to make it through these challenges; getting upset or anxious when these situations happen will only damage your ability to do your work. Instead of focusing on how concerned you are about client reactions, focus on getting your current assignment done to the best of your ability. It takes a calm, clear mindset to succeed at self-employment. Those who don’t have effective stress-management skills or get easily frazzled need not apply.

10. Get the support you need

You don’t need to tackle this portion of your life alone. Jay Abraham states that one of the best things you can do as your own CEO is to find a coach who won’t settle for less. Though we are raised not to ask for help and instead act like we know all the answers, the truth is that no one exists in a vacuum. It’s our responsibility to find the right people to help us succeed. If you’re ready to discover the advantages of being your own boss, get involved in Results Business Coaching and find a mentor who can help you through the process. 

Professional events are another way to find community. In addition to teaching you the real-life skills you need to be your own boss, Business Mastery will connect you with a group of like-minded professionals who could become a lifelong support system. You’ll hear stories of success and perseverance, get valuable advice and learn to crush your obstacles and celebrate your successes.

Ready to be your own boss?

Stop thinking about becoming an entrepreneur and get the skills you need to take massive action at Business Mastery.