How to Start Working for Yourself

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What does it really take to work for yourself? Going down the path to self-employment is only as impossible as you make it. Learn how you can make the leap to running your own business.

Maybe you've dreamed of starting your own business, but you've hesitated to dive in because you don't know how to work for yourself. Having made the leap, I can say it’s not as intimidating or improbable as it seems.

Did you know running your own business used to be the norm? The Industrial Revolution of the 19th century ushered in the era of working for companies. Technological changes transformed how people earned a living back then, and the rise of digital technologies and the internet are doing it again today, making it easier than ever to transition to self-employment.

Benefits of working for yourself

It’s not difficult to imagine the benefits of working for yourself. A number of advantages easily spring to mind, but here are a few of the factors that usually drive people to entrepreneurship.


Choosing to start a business is about seeking freedom. The freedom to pursue your passions while earning a living from them. The freedom to set a schedule that works with your life. The freedom to grow and evolve as a human being on your terms, not based on the needs of a corporation.

Your business is your baby, so pouring time into it pays you dividends directly, unlike a traditional employer relationship. It also provides a flexible schedule -- one of the great allures of working for yourself.

If you work at home, you can take a day off to be with a sick child without the risk of raising the ire of your boss. Or you can structure your days to optimize towards a balance between your business and commitments to family and yourself.

Decision-making power

It’s your business. You call the shots. You make the final decisions. No more spending hours making a case for your ideas to the boss. If you want to try a concept, go for it.

This is also one of the great allures of being self-employed. You tackle the work in the way you see fit. You evolve the business in the direction you want it to go. You build a company culture that reflects your values. It’s all yours to create and shape.


In the beginning when you’re trying to capture your first clients, it may seem like the income you generate is a downside. In reality, over time, you can exceed the income you made at a traditional job.

That’s because there’s no ceiling to what you can make. As long as you keep growing your business, your income potential is unlimited. You’re not at the mercy of an employer deciding how much, or even if, a pay raise is warranted.

Consider the case of Jack Ma, a schoolteacher who decided to launch an e-commerce company called Alibaba at the turn of the century. The internet was just ramping up back then, and few people were comfortable with online purchases. Twenty years later, Jack Ma retired after becoming the richest man in China.

What to consider if you’re deciding to work for yourself

When considering how to work for yourself, dwelling only on the benefits of entrepreneurship can paint a picture that's a little too rosy.

In reality, there are plenty of downsides in addition to the upsides, and that’s why many choose to work for someone else. Reflect on these factors before deciding to work for yourself.

Motivation for working from home

Examine why you want to start a business. Is it because you’re frustrated with your job? Are you looking at self-employment as a means to make lots of money? If negative emotions like anger or greed are your catalyst, then you’re not ready to launch your own business.

You should be passionate about the work you’ll do and the business you’ll build. Otherwise, you won’t possess the motivation to deliver a great experience to your customers. Without that, it’s a tough road to build up clientele and generate the revenue to stay afloat.

Uncertainty when working for yourself

Predictable income comprises one of the key benefits of a job. You know how much to expect with each paycheck. You lose that predictability when working for yourself.

The natural ebb and flow of business means income fluctuation becomes the norm, especially in the beginning as you build up clientele. Also, your business is susceptible to macroeconomic factors like a recession. Your company may do well when the economy is booming, but you have to plan for the eventual downturn.

If a predictable income is paramount, avoid starting your own business. If you can adjust to income uncertainty, then be sure to save up enough funds to cover personal and business expenses for several months that you can fall back on if necessary.

Multiple roles when you become your own boss

An often underappreciated consideration of working for yourself is that you need to wear many hats. With an employer, you have support in the form of an accounting department, a marketing team, human resources, customer service reps, and so forth. As an entrepreneur, all those roles fall onto you.

Imagine you're a freelance photographer who has no idea how to build a website. You'll need to earn enough money to hire a web designer or grit your teeth, grab some CMS software, and do it yourself. The same goes for generating sales. You’re the main (perhaps the only) sales rep for your own company, so you have to become accustomed to sending out networking emails in a professional email format as well as other sales activities.

If taking on these additional roles is anathema to you, stick with your day job. Otherwise, be prepared to take on more than just the product or service you’re selling when you start looking into how to work for yourself.

How to know if you’re ready to start working for yourself

There's an array of books and articles that explain how to work for yourself and make money. In reality, the ways to work for yourself can’t be summarized in a succinct step-by-step guide.

Starting a business is an ongoing process, not a one-time event. Here’s how to tell if you’re ready for that journey.

1. You're focused and committed

When considering how to work for yourself, first you must possess the mental focus to establish and grow a business, and with that, have a strong commitment to yourself and your customers. Both must be in place to succeed.

This is why many people start with a side hustle while maintaining full-time employment. They prove to themselves that they have the mental dedication required to run their own business and the ability to earn income from it. After that, they drop the job to concentrate on their company because, like any relationship, your business withers without attention.

Once you’ve launched your business, it takes willpower to stay focused on work tasks. With no one to answer to but yourself, it’s easy to fall behind or bite off more than you can chew. This is particularly true for freelance workers who usually run a business alone; if they get sick or injured, the work piles up since no one has their backs.

To grow your business past the early stages, focus and commitment again come into play. It’s tempting to grab every income opportunity that comes along even if it’s not related to your business mission or long-term goals. Don’t relent to the temptation. If you do, you end up using precious time and resources on a money grab, and it pulls you away from the direction you’re trying to go with your company.

For example, an entrepreneur I know started an outdoor preschool, but she won’t enroll any child younger than two-and-a-half years old. Rather than pursue any enrollment to make money, she wants to focus on giving preschoolers a valuable learning experience, so they must be old enough to possess the stamina for an outdoor environment.

2. You have a viable product-to-market fit

Having passion for your pursuit is only part of what’s required. You also need to have a product or service that fulfills a market need. Otherwise, you won’t find customers.

Here’s how to determine that fit.

  • What sets your business apart from competitors? Establish how you want to convey your unique business brand and proposition by formulating a positioning strategy. This also plays into how to market yourself.
  • Who are your ideal customers? What characteristics do they exhibit? How can you reach them to raise awareness of your business offerings? Define your customers through buyer personas (a profile of the customer characteristics that fit your offerings), then implement customer segmentation to align your product or service as well as your marketing strategies to the right groups of clients.
  • Is your product or service fully fleshed out? You must have at least a minimum viable product (an MVP, one that meets the most basic needs of a client) to put in front of customers. Otherwise, your idea may still require more time to build up to the MVP stage before you have an offering to sell.
  • Test various digital marketing tips and evaluate how you’re generating most of your customers. Also interview any clients, even those who rejected your offerings, to gain insight into what to improve. These learnings allow you to determine if you’re at the MVP level, and if so, to zero in on the aspects of your offerings that are the best fit for a particular set of clients.

3. You're ready to put an end to auto-pilot

With traditional employment, not only do you gain a predictable income, but part of your earnings are diverted to a 401(k) account or another retirement plan, and health insurance is provided. You work a predetermined schedule. You get vacation time. And a boss tells you what you need to do. It’s a very comfortable scenario. Starting your own business means an end to this existence.

If you’re ready to turn off the auto-pilot and begin defining the details of your life, such as what retirement looks like, then starting your own business makes sense. Yes, predictability goes out the window. In exchange, you make the choices for your life that support the goals you want to achieve.

To get to a point where you’ve outlined decisions for your business, start with a plan.

  • A traditional small business plan is a good idea to run through even if you don’t intend to seek funding, and mandatory if you do. It requires you to include components such as financial projections, and this provides an opportunity to reflect on the elements of a successful business. The U.S. Small Business Administration offers business plan examples to help you get started.
  • In addition to the business plan, perform planning for items such as health insurance, retirement, amounts to set aside for your quarterly tax filings, and the minimum income you require to pay your own expenses, like rent and groceries, in addition to those of your business.
  • A third type of plan is also required to drive customers to your business: the marketing plan. This strategy outlines the best methods to reach customers, such as making a newsletter. Fortunately, once you’ve determined a product-to-market fit, many elements of the marketing plan will naturally fall into place.

4. You understand failure is not an option

In my career building software products, a familiar refrain was, "Failure is not an option." This doesn’t mean you cannot make mistakes; quite the opposite. It meant launch your offering, collect real-world performance data, evaluate what’s working and what’s failing, then address the failure until it’s resolved. In short, keep tackling the problem until a solution is found.

This same mindset applies to launching a business. You may think you have the greatest idea in the world, but when you evaluate the product fit to your identified market, you may discover the idea isn’t ideal. So be prepared to adjust or even pivot to a different business model, if necessary. Staying flexible and open-minded to change is what being an entrepreneur is all about.

To determine what may be going wrong with a struggling business, try these steps:

  • Collect as much data as possible -- through customer interviews, surveys, analyzing website traffic patterns -- to find areas for improvement.
  • Change one aspect of your existing products or services that can have a material impact on your business, such as the pricing strategy, then collect more data. Changing more than one facet at a time can make it difficult to determine the impact of the change, so don't make too many adjustments at once.
  • Continue tweaking and collecting data about the change until results improve. This means you’re on to a solution.
  • When results improve, continue this pattern of testing until your offering is performing well. And to be honest, this approach really never ends, because you’ll want to continually look for ways to evolve your business.

If you’re unwilling to adjust a product or service that isn’t working for your customers, you’re probably not ready to work for yourself. Being your own boss doesn’t mean you have no one to answer to; you always have to address customer needs, which change over time.

5. You're excited about continuing self-education

Speaking of change, the one constant for a business is continuous evolution. Acquiring new skills and knowledge is a big part of that.

Perhaps your passion for photography doesn’t translate to the spreadsheets or other record-keeping required to prepare for taxes. Or maybe you have no clue how to market yourself with tactics like email marketing, an effective but complex marketing channel necessitating the help of email marketing software.

Being proactive and educating yourself is a big part of learning how to work for yourself. Some sources where you can find help include the following.

  • The internet serves as a natural resource for information.
  • Check with your local library, community college, or even consider online courses.
  • Leverage YouTube. There’s usually a video about any topic on YouTube.

This learning also extends to your inner workings, such as getting out of your comfort zone. For instance, if you’re not keen on selling yourself or your work, you’ve got to break out of that mindset to capture customers. If you don’t attend networking or industry events, you’ll have to change that behavior, too, so you can gain contacts who can help further your business. Learning how to work for yourself means you must be open to constantly evolving your company and your own habits.

Final advice about working for yourself

Because transitioning from a job to self-employment is a big life change, know that it takes months for the transition to fully sink in. Give yourself the breathing room to make it a successful transition by maintaining your health and balancing other life commitments with your business.

Doing so makes the challenge of learning how to work for yourself less stressful, particularly if you’ve done some of that financial and business planning I mentioned. It also gives you the space to enjoy what you’re doing.

Taking back your life is one of the key reasons to become your own boss, so be sure to leave time to bask in your newfound joy.

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