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So you want to be your own boss? Here's how to do it right

June 23, 2023 - 18 min read

Smiling-Businesswoman-Standing-With-A-Laptop-be-your-own-boss

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Pros and cons to becoming your own boss

4 self-employed job ideas

5 entrepreneurial traits

Is it time to become your own boss?

12 final tips for becoming your own boss

Make your move

Not all workers are cut from the same cloth. While some enjoy the structure and direction an organization provides, you might find fulfillment in having the freedom to lead the show.

Maybe you enjoy flexibility, running meetings, or delegating work. Or perhaps you have a brilliant idea you’re sitting on. Whatever it is, running your own business puts you in the driver's seat. 

Being your own boss offers immense independence — but it also comes with increased responsibilities. If you’re going to succeed, you must be flexible, patient, and plan carefully. But if you can’t stop thinking about turning your side hustle into a full-time gig or a business idea into reality, it’s likely worth the effort.

Pros and cons to becoming your own boss

You might idealize being your own boss, picturing total freedom and unstoppable revenue. But it's not always sunshine and roses. Professional freedom is a double-edged sword: you set your own schedule and increase your earning potential but also wear all the hats and are on the hook for every aspect of your business.

Here are some pros and cons worth considering before you start. 

Black-Man-Writing-Notes-In-Desk

Benefits

Greater earnings

If you’re a regular employee, industry standards determine your salary. And if you work hourly, you may find it challenging finding a fair wage. As of 2022, the average American hourly worker earned $11/hour, just a few dollars above the $7.25 minimum. 

While overhead costs, market fluctuations, and competitors constrain an entrepreneur or freelancer's bottom line, you have one less limitation: your employer doesn’t control your annual salary or hourly wages. 

You might find it more difficult to build a steady income compared to accepting a salary from an employer. But picking clients, understanding the value of your product or service, and effectively managing time and costs can offer you financial security faster than climbing the corporate ladder.

Flexible schedule

Whether you want a vacation, to spend more time with your kids, or to attend to your mental health, you can manage your schedule if you work for yourself. 

Self-employed workers aren't above time constraints — you’ll still have deadlines or clients that expect you to be responsive and available during specified hours. But you have the freedom to adjust your schedule or take a break if you want. 

And one study found that Americans spend about 50% of their workday performing unnecessary tasks. Working independently means making the most of your time and creating workflows that give you the work-life balance you want. 

Increased happiness

Your employment affects your happiness. When you’re happy at work, it carries over into other areas of your life. And having the freedom to follow your dreams and work on something you care about can fill your life with more meaning and purpose, increasing your happiness levels in every area.

More accomplishments

Starting a business is daunting — and impressive — work. Along the way, you’ll achieve so many things you never thought possible, and accomplishing these interest-aligned goals can improve your emotional well-being. You’ll also likely experience a confidence boost that’ll motivate you to continue forward, in turn accomplishing more and more as you go. 

Woman-sitting-on-couch-working-at-home

Disadvantages

Slow progression

For nearly every business, the first few years are tough. According to a report by American Express, earning a return on investment and becoming profitable takes about 1–4 years.

And if you’ve never done this before, the learning curve is steep, finding customers is slow, and building trust with them takes time and effort. It might be a while before you’re reaping the financial rewards. 

Greater responsibilities

Being your own boss might mean being your own:

  • Accountant

  • IT support

  • Project manager

  • Marketer

  • Salesperson

  • Customer service rep

  • Logistics coordinator

Depending on your finances, you might need to hire help. But even so, at the start, you’re the one everyone’s coming to with questions, and that’s a lot of responsibility. You’ll want to understand various crucial business aspects to effectively carry this weight.

When going solo, you’re also responsible for your well-being and future. You don’t get employer-established health benefits or retirement funding packages, so make sure you’ve explored your options for individual support. 

Inconsistent income

Working on your own makes you more vulnerable to changes in the market or costly incidentals. If a big contract suddenly drops, a recession hits, or competition overwhelms the market, you'll feel it financially. Before you start, create a robust financial plan with buffers for unexpected setbacks.

You still answer to someone

Being your own boss doesn't mean you work in a vacuum. Ultimately, your clients or customers are your boss. While you might experience a bit more agency regarding your schedule, their needs must be top priority for your business to succeed. 

4 self-employed job ideas

Independent work is at an all-time high. In 2022, freelancers represented 39% of the American labor market, with even representation across education and qualification levels. 

Here are some of the most in-demand jobs

1. Nursing

According to the Bureau of Labor Statistics (BLS), nurse practitioners will be the fastest-growing profession through 2031. And with a nursing license, you can work independently as a medical-industry product or legal counselor. Or, you could gain certification as a legal nurse consultant to assist attorneys.

2. Web development

The BLS expects web development to grow 23% throughout the decade. And a certification program might be all you need: increasingly more employers are embracing workers with certifications over degrees.

If you’re interested in design and coding, you can apply your skills to nearly every industry.

3. Market research analyst

Market research analysts typically provide information to sales, marketing, and product development teams regarding a company’s target audience, industry trends, and market conditions.

If you have strong critical-thinking and analytical skills, you could provide this important service to businesses in nearly any industry. And luckily, the BLS expects the need for market research analysts to grow 19% through 2031.

4. Business consultant

If you have a business degree or extensive managerial experience, you’ve likely developed the leadership skills and know-how business owners and entrepreneurs find valuable. Depending on your expertise, you might consult with companies to discuss how to streamline human resources policies, build business best practices, and create strategic marketing and sales strategies. 

Mature-Leader-Listening-To-Employees

5 entrepreneurial traits

Because you’ll wear so many hats, being your own boss requires extensive skills. Beyond the technical skills necessary to excel in your chosen industry, you’ll also need to continuously polish your soft skills and develop leadership traits to navigate the ups and downs of starting a business. 

Here are five traits you can foster to think like an entrepreneur:

  1. Patience: Success isn’t linear, and you’ll likely fail, make mistakes, and navigate setbacks. Practicing patience helps you develop a resilient mindset, keep your cool, and accept challenges as part of the growth process.

  2. Self-discipline: With so much responsibility on your shoulders, you must remain disciplined to keep moving forward. Especially at the start, if you slip up or miss too much work, there’s nobody to blame but yourself — and several missed deadlines or objectives could greatly impact your business’s success.

  3. Organization: Businesses have so many moving parts, and the only way you’ll stay on track and juggle every role you’ve taken on is if you’re organized. Strong organization skills help you remain focused and on task while reminding you of important obligations. 

  4. Future-mindedness: To stay motivated and understand why you’re doing what you’re doing, you must never forget the bigger picture. Future-mindedness also ensures you consider important long-term factors, such as how an industry or target audience might develop.

  5. Empathy: The key to your success is building positive relationships — be it with potential clients or networking with other professionals. And empathy helps you show genuine interest in what your target audience wants or what that professional connection says.

    Making people feel listened to and understood increases your likeability, in turn increasing the chance a potential client signs up or a networking contact considers you for an upcoming opportunity.

    Plus you’ll better understand how to deliver something valuable to your customer base or sell your services to a contact. 

Is it time to become your own boss?

Female Consultant Having -Meeting-With-Client-In-Office

If you're naturally independent and free-spirited, working within the confines of an organization may block your sense of freedom and purpose. Here are a few ways to know it's time to be your own boss:

  • The dream doesn’t go away: You've got a million-dollar idea for a business, product, or service and can't stop thinking about pursuing it. You may have already turned it into a side hustle or written the business plan.
  • The corporate ladder doesn’t interest you: The corporate ladder feels more limiting than motivating, and office politics get in the way of meaningful work. You feel micromanaged by most managers, like too many meetings could’ve been emails, and that company goals no longer align with your personal values.
  • You cringe at the status quo: Many businesses have well-defined structures that make organizational change difficult to carry out. And the larger the company, the more difficult cultural innovation is to manage successfully. If you want to build an innovative and creative business structure, striking out on your own may be the best route. 

12 final tips for becoming your own boss

You've worked up the courage and have a product or service idea — time to sit down and plan. Here are 12 things to consider during the planning process:

  1. Double-check that self-employment is right for you. Talk to colleagues, mentors, and friends who’ve built successful businesses to understand the process and set realistic expectations.
  2. Consider keeping your day job and starting part-time. This’ll help you get your footing and work out any kinks.
  3. Thoroughly research your product or service’s industry, target consumer, and market opportunities.
  4. Be honest about your current skill set, defining the technical, hard, and soft skills you need to bring your business to fruition. 
  5. Analyze your finances and budget your cost of living and startup costs. Consider whether you require a lot of money for overhead or can start your business with existing resources.
  6. Decide on the best operating model for your business and how you'll interact with new clients, be it freelance, consulting, or e-commerce. And determine whether operating from a home office or in a rented office space makes the most sense.
  7. Outline every resource you need to start, from business loans to certifications and office supplies.
  8. Develop branding, marketing, and social media strategies, and consider consulting with a branding agency.
  9. Work with lawyers and accountants to ensure your enterprise is up to code on legal requirements and bookkeeping.
  10. Create a well-developed business plan that includes:
  11. Share your business plan with industry professionals and stakeholders to gain investment, support, and clients. 
  12. Your business depends on you feeling mentally and physically healthy, so remember to prioritize your health. 

Make your move

Starting a business is daunting, but the hard work pays off. Being your own boss means you gain the freedom to develop a workflow and schedule that works for you. And you’re pursuing something meaningful, which means you’re never wasting your time or feeling purposeless.

Plus the professional development you’ll gain from this experience is next level — you’re becoming a more resilient, skilled, and authentic you with every step.

Invest in your career

Get your promotion. Make your career change. Build the future you dream about. And do it faster with a world-class BetterUp Coach by your side.

Invest in your career

Get your promotion. Make your career change. Build the future you dream about. And do it faster with a world-class BetterUp Coach by your side.

Published June 23, 2023

Elizabeth Perry, ACC

Elizabeth Perry is a Coach Community Manager at BetterUp. She uses strategic engagement strategies to cultivate a learning community across a global network of Coaches through in-person and virtual experiences, technology-enabled platforms, and strategic coaching industry partnerships.

With over 3 years of coaching experience and a certification in transformative leadership and life coaching from Sofia University, Elizabeth leverages transpersonal psychology expertise to help coaches and clients gain awareness of their behavioral and thought patterns, discover their purpose and passions, and elevate their potential. She is a lifelong student of psychology, personal growth, and human potential as well as an ICF-certified ACC transpersonal life and leadership Coach.

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