Corporate, Startup or Freelance: Which Career Path Should You Pick?

Today’s job landscape is changing rapidly. Globalization allows companies to reinvent their business models and cost structures. New technology such as robotics and artificial intelligence threatens millions to lose their jobs in the near future. As the workforce tries to navigate through this changing tide, many startups have emerged, and the use of flexible work arrangement has become increasingly popular.

This means working for big corporations no longer seems to be the only, or the most appealing, career choice. However, with options comes confusion. Corporations provide stability and reputation. Startups offer excitement and bigger impact within the organization. Freelance gives the most flexibility and variety of work. How do you know which career track is the most suitable for you?

To answer this question, it is important to become familiar with the unique work environments and the differing mentality required to succeed in each type of work before getting started. Let’s first take a deeper look at corporates - they are great to work at, and not just for their stability.

Corporate: A Well-Oiled Machine

“Great things in business are never done by one person. They’re done by team of people.”
— Steve Jobs, Co-founder of Apple

Steve Jobs has turned Apple into one of the most successful corporations in the world, so it’s safe to assume he understands a thing or two about building and running a world-class corporation. Like he states above, businesses are a collaborative effort with a team of people each fulfilling a task - much like different parts of a machine. It is only when these parts work in unison with one another do we see good results. When individuals are part of such a large-scale operation, their job experience is shaped by some characteristics unique to corporations.

1. Good Work Life Balance with Predictability

An ideal corporate job allows you to have a nine to five schedule with few outside hours. You are free to spend your evenings relaxing in front of a TV and weekends with your family. You will also have time to develop a hobby or take on an exciting side project.

Working in corporate also earns you a stable, and often higher income as compared to startups and freelancers. The predictability offered by the fixed hours and a stable income makes corporate jobs an attractive choice for those who enjoy planning for the future or those who prefer financial security.

In addition to hours and income, predictability is also reflected in the tasks you perform at corporates. There is usually more structure and order in the workplace, and business results of the previous year are often more indicative of next year’s performance. If you thrive in a more structural work environment, prefer to go to work everyday knowing exactly what you will be working on, or enjoy working with large data sets to detect trends and patterns, then corporates are still the way to go.

2. Gain Job Satisfaction as a Specialist

In a large organization with so many spinning parts, you often start your career by being assigned a very specialized area of focus. You will dedicate most of your time on a few select tasks. You will get to work with seniors who are experts of your specialized area of focus. And eventually, you will be an expert yourself as you become adept at your job. For people who enjoy the process of mastering a skill, and those who enjoy being recognized as the guru of a specialized area, this can deliver a high level of job satisfaction.

Another critical skill set people pick up at corporates are soft skills. Due to the number of people you have to work with, you will develop communication skills, learn how to get buy-ins from top management or cross-functional team members, and even get a taste of constructive office politics.

3. Motivate Yourself with Extrinsic Factors

Let’s face it, who doesn’t like getting a pay raise, promotion, or other material rewards? Employee benefits and office perks such as free food and gym membership are also usually celebrated. The prestige that comes with a “big name” not only makes you the envy of your friends and family, but will also open a lot of doors for you after you leave the organization. While people might turn their nose up at the concept of being motivated solely by money or perks, you should choose a job that can offer the right level of extrinsic value for you.

Working for corporates obviously has its downsides. Predictability and specialization can become boring. With so many people vying for a promotion, office politics can get ugly. Getting your voice heard in a large organization can also be difficult. But not every corporate is the same; with company review sites like Glassdoor, you can always look for corporates that suit you.

Often hailed as the “safe” route, there is a wealth of job search sites posting corporate jobs if you ever decide to go down this path. Or you can read on to find out about startups, often thought of as the polar opposite of the corporate life.

Startups: Living for the Highs

“Chase the vision, not the money; the money will end up following you.”
— Tony Hsieh, CEO of Zappos

Startup fanatics are often driven by company vision much like Tony Hsieh aptly puts, sometimes because they want to make a dent in the universe, other times because they believe that the company vision can lead to enormous financial success. As amazing as both sound, people who have never worked in startups still have very little understanding of what it is really like to work in one. To determine if you will be happy working in a startup, you have to first learn about its unique culture and working environment.

1. Work in an Ever-Shifting Environment

Startups are dynamic and fast-paced. You are expected to deliver results from day one. Your tasks vary as you will be asked to wear multiple hats. What you are working on today may get thrown out of the window tomorrow due to a change in competitive landscape or resource constraint. People often attribute such a volatile environment to bad management, while in reality this is an embedded feature of startups as they fight for survival or seek rapid growth.

As a result, working at a startup is usually more demanding compared to corporate or freelance jobs. Often times you are not constrained to normal work hours and may even be required to work weekends before an important deadline. Since you are expected to dabble in multiple fields, your focus shifts from marketing to company finances to logistics to anything else that needs to be done - all in a day’s time. In the startup world, job descriptions are a rough outline at best.

2. Learn Quickly and Independently

Given the fast pace and the small team size, working at startups generally gives you the opportunity to try different things out. Interested in marketing? No problem. Want to learn about fundraising? Go right ahead. It is for this very reason that startups are a prime learning opportunity, but you will have to be a fast learner. You will also need to be ready to put time and effort into learning things yourself as it is likely a first for everyone. You may get to speak to the CEO and get their direct input, but you might not have a formal training program or a manager hand-holding you throughout the learning process. In short, the world (of learning) is yours if you want it, but you are on your own.

3. See Your Efforts Come to Life

The path from idea to execution at startups is relatively short as opposed to large organizations since decisions are often made quickly by just a few people. This means you will get to see the impact of your work much faster. Moreover, due to the small number of employees in startups, the above-mentioned impact will likely be significant as your work performance is on full display. If you are a result-oriented person or a “builder”, or if you gain job satisfaction from seeing direct results, startups may be your calling.

Startups are more suited to those who are flexible and enjoy living life on the edge. Working in such an environment has its shortcomings though. Startup employees tend to have lower salaries. Full-time employees are often compensated with equity, but the high fatality rate of startups means equity doesn’t always translate into financial reward. Also, since startups are inherently risky in nature, you may suddenly find yourself without a job.

But keep in mind: With great risk comes great rewards. If these features strike a chord, AngelList is a website with a large database for startups, or you can try to use Jobalaya to explore and discover less-known companies based on specific features that might interest you, such as whether they provide flexible work hours or free food.

If both corporate and startups do not seem like your cup of tea, and you are someone who is more of a lone wolf, the next career path may be for you.

Freelance: A Free Spirit

“The life of the professional writer – like that of any freelance, whether she be a plumber or a podiatrist – is predicated on willpower. Without it there simply wouldn’t be any remuneration, period.”
Will Self, English novelist

The importance of willpower, though applicable for both corporate and startups, is no more apparent than for freelancers. Unlike a large organization or startup, freelancers are individuals operating on their own, giving them the benefits as well as the pitfalls of autonomy.

1. The Client is King

Since freelancers are their own boss, they do not need to keep any higher ups happy and there is a complete absence of petty office politics. This doesn’t mean you have no one to report to though. You deal directly with the client - some are easier to satisfy than others. To be successful, it is vital to have a solid understanding of what your client wants. In other words: Strong communication skills. With outsourcing on the rise, understanding how clientele of different cultures operate is a must to build up a large client base.

2. Sales, Sales, Sales

Many people have the impression that freelancers spend all their time working on projects for clients. In reality, you will spend a large portion of your time selling and pitching your skill set to potential clients. People can outsource skills such as accounting, but only you can be your own salesman. You have to put yourself out there and build up a reputation - if not, you will quickly find yourself out of work. If you are someone who hates selling yourself, all is not lost. Agencies could be the answer to your problem. They build clientele relationships for you so you can focus solely on completing projects.

3. Complete Autonomy

Being proactive is one of the top qualities a freelancer must possess. Since you get to choose your own projects and set your own hours, it is all too easy to go outside and enjoy the sunshine even with a deadline right around the corner. There are no coworkers chasing you up for work or KPIs to hit. You are responsible for keeping yourself motivated.

Autonomy resulted from working alone also brings another side effect. Unlike in a corporate, you have no one to ask for help or fall back on, so you will either have to teach yourself or reach out for help. Asking for help is not as easy as it sounds when you work alone, often from home. As a result, some freelancers find it hard to maintain an abundant social life. You have to put real effort into meeting people as opposed to the workplace where you are naturally exposed to them. Faced with this problem, many have turned to co-working spaces, which are reported to have productivity rates even higher than those with office jobs!

If you are considering this career path, it is important to keep in mind that the income of freelancers are reliant on the individual’s skill and there is no guarantee of work. Even so, freelancers are earning more on average than before. To those ready to get started, Upwork and Fiverr are two of the biggest platforms to find freelance jobs.

Making the Big Decision

Now that you have a little more understanding of corporates, startups, and freelance jobs, let’s come back to the original question: How do you know which career track is the most suitable for you? With so many factors in play, the decision making process can be daunting. Not to mention, we human beings are irrational creatures - we make plenty of impulsive decisions without realizing what really suit us the best.

To help you make a sound career decision, we recommend using a point system to objectively assess your preferences across the three career tracks. Here is an example of an effective point system:

Based on this exercise, I’m clearly in the right space working for a startup! You can always add to the list of questions to make sure it accounts for all the factors that matter to you. The key to this exercise is this: Be honest with yourself! Don’t answer based on who you wish to be, but who you really are.


The point system is only an aid to help you decide on a career path. You should also take into account your long-term career goals as well as your current life and career situation (see Top Common Mistakes When Selecting a Career). On the other hand, it is rare for someone to be completely aligned with a single career track. You might crave for structure and order but also score highly for traits of a startup employee. In this case, a job at a later stage startup could be a wise choice as more systems and processes have already been established compared to an early-stage startup. When you have finally made your choice, you can start exploring great companies in your selected career path. If not, decide what is most important to you and make your decision accordingly. But don’t worry if you feel you haven’t found your calling - if you ever find that a certain career path is not for you, you can always switch tracks!

Kira Buen
Kira is a content marketer at Jobalaya. She loves to travel, hike, and due to her short memory - can enjoy reading the same book multiple times as if it is her first.