How To Tell If You’re Ready For A Second Career

“How I earned a 9-digit income per month” and similar content is ubiquitous on social media nowadays. Such content is not meant to pressure the audience, but its popularity does imply something.

How can I increase my income? How can I land a job I’m passionate about? Each question is challenging enough. But as human beings, we all long for an answer that can satisfy both.

If your 9 to 5 job isn’t what you love, or you simply want to diversify your income, or both, this article might help you realize when you are ready for a second career.

What is a second career?

Before we dive into details, it is essential to clarify why the term “career” is used instead of “job” in this article.

From my perspective, a second job is a side hustle where you use the same professional skill set as in your main job to earn an additional income, as in the case of a graphic designer who takes on freelance projects, such as advertising and branding design.

Meanwhile, a second career requires you to have other skills to develop your personal brand before you start enhancing it or turning it into your first career. The same graphic designer, for example, can launch a personal blog to share knowledge or sell courses.

Your second career might have nothing to do with your main one. It can be as simple as having a hobby and aspiring to invest in it. For instance, a graphic designer passionate about travel can start video blogging about his trips, experiences, and tips that might be helpful to others.

“Suppose I am a graphic designer and partner with my friend to start a snack food business to earn more income. Is it a second job or career?” you might wonder.

The answer depends on why you started your business. Maybe you love doing business. Perhaps you enjoy preparing snacks, or you know where to source them.

In short, a second job is perceived as a second career when:

• You have a main job
• You are self-employed in your second job
• It is hobby-based

Knowing when you are ready for a second career

1. Master your main job first

From my experience, you should focus on enhancing your professional expertise to a senior or expert level before pursuing a second career, which will lay a strong foundation that includes:

A secure financial background. Being well-paid for your effort, you can afford your personal needs and have some savings while spending available time working on a second career.

An effective personal mindset. On the road to expanding your expertise, you will simultaneously cultivate and harness your mindset, a much-needed asset in the face of a heavier workload that comes with a second career.

Self-discipline. A high level of self-discipline, at least at level two out of four, can help you make the best use of your willpower to resist temptations and achieve your goals.

“Genuine” values. Those values include your experiences, insights, professional skills, or effective mindsets. You can tap into them as an abundant resource for your second career (for example, sharing knowledge or launching a course.)

Self-understanding. The journey of self-development, filled with ups and downs, feats and failures, will help you realize the values of perseverance and which hobby or passion is better suited for your second career.

2. Build a strong personal brand

Your second career can start with building a personal brand in case you have yet to reach a senior level.

The ultimate goal of personal branding, drawn from my experience though I am not an expert in this field yet, is to ensure that “we get paid to be ourselves.”

In other words, besides continuously enhancing our professional expertise, we should be able to lead our life in our preferred way and earn money from that lifestyle before starting a second career.

I have adopted this mindset to build my personal brand through writing with three guiding principles: Life – Value – Balance. In other words, I only share what comes from my experience and has practical values without overemphasizing my ethical standards.

I believe this mindset will contribute to a sustainable personal brand. Then I equip myself with essential skills to “package my experiences,” such as writing scripts, filming, video editing, voice recording, and publishing on suitable channels. However, this avenue is often riddled with instability and competition, which leads to my next point.

3. Understand both sides of a second career

A second career can benefit you in many ways that you might be well aware of before clicking on this article. You will be financially secure with multiple monthly streams of income while having opportunities to explore other passions or talents. You’ll experience more joy and happiness in life. Your network will grow beyond professional relationships in your main job. You’ll expand your expertise, diversify your skill set, and enhance your problem-solving.

As the old saying goes, however, every coin has two sides. A second career is no exception, and its downsides are worth considering.

Time pressure. Juggling multiple jobs is time-consuming, which can be problematic if you have poor management skills and a family to care for. Therefore, you should consider it thoroughly before making a trade-off.

Energy crisis. It takes much energy and effort, besides time, to stay productive and efficient in multiple roles while constantly developing yourself, which can threaten your physical and mental health.

Instability and competition. Your second career will face fierce competition if your hobby and secondary skill set do not set you apart. In an age of technology and digital transformation with the availability of different generative AI tools, your second career can hardly thrive if it offers no distinctive value to society.

Distraction. Time pressure and energy crisis can shatter your attention, causing you to lose track of both careers. Things might go sour over time, undermining your spirit and enthusiasm.

Conflict with your main job. This conflict can happen in two scenarios. You take on a second job though your employment contract prohibits you from doing so (which is a common practice for senior-level positions and in corporations.) Or, your side gig lowers your main job performance, and your boss requires you to choose one over another. As a result, you are pressed to be deliberate about your career path.

I decided to build my second career in 2016–2017 after working for several years and saving up a pretty amount which was not enough to buy a house, but enough to invest in something else.

Starting from my experience in managing family-owned rooms for rent and my preference for comfy homestays when traveling, I decided to invest in the accommodation business by renting small apartments, refurbishing them in modern and minimalistic styles that captivate youngsters and foreigners, and becoming a host on Airbnb.

Everything went well in the first year, and luckily, I could break even after three to five months for each apartment. This source of passive income steadily increased every month. Also, interactions with diverse guests added to my excitement and boosted my optimism.

However, the second year was a different story due to many adversities getting in the way. Due to the guests’ short stay, more mundane tasks, such as checking rooms, registering temporary residence, and processing requests, occupied most of my time. Consequently, I got distracted and delivered a less-than-ideal performance in my main role as a product designer for an American-based studio. It came as no surprise that my boss noticed it and required me to solve the problem immediately.

To make the matter worse, the landlords, taking note of a money-making opportunity, began interfering with more demanding requirements, even terminated the rental agreement before the due date, and copied my business model. That I run the accommodation business without owning the property caused dependence and many issues, much like a gourmet cannot cook good food.

I realized that running an accommodation business was not what I enjoyed doing. Finally, I decided to shut it down after two years in operation and wholeheartedly refocus on my main job as a designer.

The whole project was not a financial failure. Yet, I failed to manage my time and emotions effectively and foresee the many challenges getting in the way.

This experience has taught me that if I have a certain level of readiness for potential problems, as mentioned above, my second career is more likely to thrive.

Final words

Experience can be likened to an old piece of clothing that might fit you perfectly but no longer suit your taste. You can refer to mine as you are seeking to develop a second career. If your current job is aligned with your passion, you don’t have to worry too much about a second career.