Escaping the Cube:  Why, When, and How Workers Leave Corporate America to Pursue Entrepreneurial Ambitions

Post Date: July 22, 2020

Increasingly, American workers are choosing to leave the corporate world and to start their own businesses.

These departures are fueled by increasing optimism in the country’s economic outlook, a desire to have more professional independence, and the appeal of being their own boss.

It is worth a closer look to learn why workers are escaping the corporate cube. Why, when, and how workers leave corporate America to pursue their entrepreneurial ambitions are complex and important issues to consider.

According to the most recent U.S. Bureau of Labor Statistics (BLS) data, despite economic uncertainty caused by the COVID-19 pandemic, 1.8 million still people left their jobs voluntarily in April of 2020. Economists generally consider “quits” an indicator of healthy optimism, as a good number of those who leave choose to start their own businesses.

The rise of the freelance economy has contributed to the entrepreneurial spirit of Americans, and by 2019 there were more than 57 million doing some form of freelance work either full time or as a side hustle. It is estimated that the number of freelancers in the US will exceed 64.6 million this year and 90.1 million by 2028.

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Why Leave?

Many employees who choose to leave the safety of a corporate job do it for the freedom and flexibility that comes with starting a business. In addition to the wealth potential, running your own business gives you the opportunity to control your destiny.

The choice to leave a seemingly secure position in corporate America may seem risky. However, in many cases, the climate and culture in the corporate world leave a bit to be desired. Here are a number of other reasons people are choosing to leave:

    • Office Politics. When you become your own boss, the nastiness of office politics is a headache you can completely avoid. You’re no longer burdened by coworker infighting, pressured to cater to the whims of a difficult boss, or forced to be a pawn in someone else’s chess game.
    • Career Control.With a corporate job, workers are not always in control of their career path. The opportunity for promotion or advancement or learning new skills is often at the whims of a supervisor.
    • Declining Benefits. In most areas of corporate life, the notions of company-provided pensions, reliable healthcare, and other benefits are long gone. More of those costs are now passed on to the worker.
    • Loyalty. In years gone by, companies earned the loyalty of their employees, providing them with opportunities and security that enabled a long, productive career with one company. Today, some corporations no longer value loyalty, and workers have to cope with ever-looming threats of layoffs and downgraded opportunities.

While not everything about corporate America is doom and gloom, there is certainly a great deal of dissatisfaction that employees are feeling about the work being done and the way they are being treated. It’s no wonder that employee engagement is only at 31 percent in America and Canada; and that number is drops to 15 percent globally, according to Gallup’s 2019 State of the Global Workplace report. There is significant appeal to the notion of giving up corporate life and considering a different type of career.

Should You Consider a Change?

There are many reasons why you might consider leaving your job. But the real question is whether you are ready to make the change. What factors should you consider when it comes to making a major professional transition?


The answers are not always obvious. You need to spend the time considering if you are dissatisfied with your current situation. If the answer is yes, then determine why you are dissatisfied. 

The decision to leave a corporate job is not one to be taken lightly. If you choose to make the leap, there are some things that you can do to make sure the switch is done smoothly and professionally.

The first thing to do is assess whether you are truly making the right choice. Ask yourself what is missing from your current work situation. What are you going to escape to if you leave? What are the opportunity costs to staying or leaving?

Here are some points to consider during the assessment:

    • Are you happy? Do you experience joy in the work you are doing? Job satisfaction is a powerful motivation. It can provide you with a sense of fulfillment and a feeling that you are part of a greater good. Not feeling that way can leave you with an emptiness that needs to be filled.
    • Are you inspired? Do you work with and for people who motivate you and whose company you enjoy keeping 40 or more hours a week? You want to be with people whose work, collaboration, and intelligent thought helps get work done. You deserve a sense of teamwork and camaraderie. You need a leader who rallies and motivates. If you do not have that situation, perhaps you are the leader who can inspire others.
    • Do you love your work? You spend years of your life at work. You deserve to live a life that is fulfilling and enriching, and that brings you joy and happiness. If you are not feeling those things, it just might be time to venture forth on your own.
    • Have you stayed too long? Do you have a sense of “been there, done that” with your work? Are you bored? If the answers to these questions are “yes,” you may have outgrown your job. 

Next, create a path for your departure. What steps do you need to take to be ready for what comes next? These steps may include additional training, skills development, due diligence on a potential entrepreneurial venture, resume updating, or additional networking.

It is likely that these steps can be taken while you are still employed. Taking the time to acquire what you need in the way of skills, information, advice, and capital while still earning a paycheck is a smart idea. It allows you to explore and, perhaps, change your path before making a career leap.

Finances are a major consideration for anyone looking to leave corporate life. Consider how you will support your lifestyle and pay the bills, while at the same time determining how you will cover the costs of a potential start-up venture.

You need to make a budget, a comprehensive business plan, and do the math. Are there living expenses that can be cut, at least temporarily once you leave? Do you have enough savings to support you and your loved ones? Is there a spouse or partner who will continue to have health insurance and other benefits to provide the security and peace of mind you need, especially when starting a new business?

Overcoming Obstacles

When you choose to leave a job, you are inevitably going to face several obstacles. Knowing what these obstacles are and understanding how to overcome them are important steps as you prepare. Here are three of the biggest obstacles and how to overcome them:

    • Financial Reliability. Keep in mind, there is one considerable advantage to working for a corporation. You know you will be getting a steady, reliable paycheck. You can count on this income to pay your living expenses, entertain yourself, and put away savings. That is one of the biggest reasons to do the planning and due diligence while you are still employed. You may also be able to start your own business, at least part-time, while you are still working a full-time job. While this can be difficult, it will provide you with financial security.
    • Increasing Debt. Consumer debt such as credit cards, car payments, and student loans can stymie your efforts to pop the corporate bubble. Before you leave, do everything in your power to reduce or eliminate these debts from your portfolio. Not only does this lessen the anxiety and strain of a new venture, but it also takes the pressure off of your initial income needs when you go out on your own.
    • The Skeptics. Friends, family members, and coworkers may criticize your choice. Skeptics abound, especially among those who are more risk averse. This is a natural reaction and it is a good idea to not take these skeptics’ words personally. The best way to overcome these naysayers is to provide them with information about the reasons you are leaving the corporate world, the thoughtfulness you have put into that decision, the work you have done to determine what comes next, and how you will achieve the success you are seeking in the next phase of your life.

What Lies Ahead

Congratulations! You have answered the questions, created the path, considered your options, done your homework, and decided to make a change. Now what?

The opportunities are limitless. You are no longer bound by the workaday rigors of a corporate existence. You can create your own adventure. What awaits is extraordinary. Consider the benefits of starting your own business:

    • You are in charge.  As an entrepreneur, you control the fate of your enterprise. You make the decisions, create the rules, establish the values, and reap the rewards related to your business. You are squarely in the driver’s seat and making your own decisions.
    • You select the staff. When you create your own business, you can bring on the employees, advisors, investors, and consultants who share your values and vision. You can build a team of people who will work with you to achieve your goals. While that is a heady responsibility, it is also an extraordinary opportunity.
    • You create the balance. A lot is said today about work/life balance. As the owner, you have the chance to set the tone and expectations that give you and your team the balance you believe is right.
    • You follow your passion. With your own business, you can realize dreams you may have had for years and help bring to life ideas that have been percolating in your head.
    • You work with the clients and customers you want. As a business owner, you can work with the markets, industries, and companies you want. You can connect with the kinds of people you want to work with, on your terms, and help serve their needs with your products or services.
    • You have pride of ownership. At the end of the day, you will leave a legacy behind that will be a testament to all your hard work.

Making It Come Alive

In order to make your entrepreneurial dream come true, you will need financial help. At Benetrends, we work with entrepreneurs to identify the types of small business funding that works best for their needs. With decades of experience in financing and advising business owners, we work closely with our clients to get them the funds that let them start their next chapter.

Our funding solutions include using an existing 401(k) or IRA account to finance your new business venture. We can help guide you through the process of creating the right corporate and internal structures to allow you to leverage retirement funds to fuel your startup costs. We work to complete the proper paperwork and filings that accelerate the process to get your funds fast.

We also provide help with startup and small business loan programs, including assistance with Small Business Administration loans, loans for women-owned businesses, and more. Once the business is up and running, we will be there with you. Benetrends offers a full range of other services that help keep your business operating at peak efficiency, including retirement plan administration, credit card processing, and insurance solutions.

Founded in 1983, Benetrends has helped more than 17,000 entrepreneurs choose an option other than corporate America. We have worked with those clients to secure more than $4 billion in financing. We are there for the long haul, working with our clients to develop plans for strategic, long-term growth and wealth management. 

There is life after the corporate world and it’s full of possibilities. Take the next step by downloading our Innovative Funding Strategies For Entrepreneurs. Then talk to our team as the next step in reaching your entrepreneurial goals.

Categories: Blog

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