Managing Your Second-Act Career

Between starter jobs and apex career moves is a world of secondary career options, to prepare you for your journey.

I have discussed before the threats and opportunities involved in such a shift in tracks, and how to recover as much of the potential as possible from your change using what you already have and being economical with what you need to learn and do.

But there are a number of shifts you can make in the latter part of your career that are possible at any time, deliver great return on investment, and boost your career potential in its final phases. Your goal is to set yourself up for the last stretch of your career to reach your “seaside position” as I called it in my previous post on Linkedin.

Your Goal

The goal you set will largely be determined by how ambitious you are, but in general you want to maximize your reputation for expertise, mentorship and leadership. These are three key capabilities that open the door for a number of high-profile opportunities. They are compatible with almost any primary career path, and serve as an “addon” of sorts, secondary careers that allow you to qualify for bigger jobs, or generate side-income to support other endeavors.

For example, if you are looking to become the CEO of an international company, the additional exposure in the media from a secondary career may give you a unique edge on the competition. If you are looking to create a startup, greater reputation may open up investments that otherwise would have remained closed to you. Any entrepreneurship requires an upfront investment of some sort, so the income from a secondary career can become a bankroll for further developments.

Secondary Careers

The key qualifiers for secondary careers are:

  • stand-alone, yet require a large degree of prior experience or skill
  • self-motivated and often entrepreneurial in nature
  • unique and tailored
  • part-time

So a secondary career is often rooted in your primary career track, but stands on itself. It borrows your prior skill and reputation, but does not continue the track, rather it runs parallel. If you were to stop your secondary career at any time, it would not impact your primary track.

It is self-motivated, because it is a decision you made, not driven by the need for monetary compensation. It is a calling, a drive or desire. Sometimes it might satisfy your own needs (for example, to put theory into practice or increase your reputation) while other times it can be for others (like a charitable organization or supporting a cause).

As you are the only one driving this secondary career, you are in control. Unless you hire a consultant to help build your secondary career up, you are in full control of what you do, how, and where.

As a secondary career, it should always remain second to your primary track. If you find that your “addons” are consuming more time and become more important than your primary career, you have to debate whether you need to tone it down, or accept that your secondary career has transformed into your primary career.

Career Opportunities

Here are some of the options I present you for a secondary career. Note that there are many more options, usually as subtle variations on the themes below. As society and technology advance, new opportunities arise.


Publishing is a time-honored tradition to get your point across. Whether you write a physical book, publish an ebook or write a blog, it is an opportunity to show your expertise to your audience, give advice and earn some money on the side. Being a published author (let alone best-selling) is a great talking point, and can alert people to your profound knowledge of the subject matter, especially in academic circles.

Writing a book or ebook takes some time, as you need to make sure that your sources, flow and writing are all of proper quality. There’s proofreading and editing involved, and as such it can take years to go from draft to finish. A blog is quicker, because it allows you to build a body of work one post at a time, but it requires the same investment in research and sources. Additionally, because a blog is easy to start, you will have a lot of competition and getting a solid readership can take even longer than getting a book published.

Career-wise the best published work aims to resolve a problem in your industry, provide a new tool or framework to perform activities, or seeks to unify disparate theories and processes into a structured, easy-to-understand whole. Your work should not duplicate or rehash what others wrote, but must add something unique to the collective knowledge in your industry. You can’t just write what you know, you have to write about what you think, feel and want to achieve. People would read your work not just for your knowledge, but your views on the industry and its future developments.

Financially being an author can become very lucrative, but in most cases you should not expect to be able to monetize this move. Unless you go best-selling, my advice is to aim for a break-even situation, where publishing costs are covered by cover charges, and any money made from advertising or affiliate marketing on your blog cover domain, hosting and premium features.

Public Speaker

Speaking in public involves taking what you know and bringing it to your audience in person. Rather than taking the time to pen down your thoughts and predictions, you will find yourself in a much more dynamic environment. You could join events and symposia and become a keynote speaker or hold breakout sessions. Perhaps you would like to join debates about industry topics, or address students and inform them about the realities of a career in your line of work. But don’t discount the power of starting a vlog, such as a channel on Youtube. You cannot filter your audience there, but this also gives you opportunities to access an audience you did not realize you had.

Public speaking requires courage. You cannot hide behind written text or infographics – your own personality and voice needs to carry your story. This can be intimidating, but it also builds character. Becoming comfortable talking to larger groups of people, debating, learning to craft a well-flowing story all prepare you for bigger roles such as C-level management or other public positions. Additionally, you have direct engagement with your audience which means you can adjust your story and flow to what works best at that moment, giving you much greater control of the effect you have on people.

Public speaking can also be a source of income, but you require a name for yourself before this happens (through your primary career, authorship or the like) and you need to have the courage to ask for compensation. Free access to the event is a good start (which will allow you networking opportunities) followed by compensation for flight and stay. Once you build up enough courage and knowledge of your costs involved, you could start asking for a fee. In the beginning you will pay to be allowed to speak, in the end you will be paid to come and speak.

A specific, charitable form of public speaking is where you advise others, for example at a school or job fair, and help others. They might need to know more about your job or industry to decide whether or not to pursue such a career. They might want to know what they really need to learn to succeed. They might need some support to conquer insecurity. But they can also teach you in turn. Their questions, their way of thinking, and how you answer them, all give you new insights and inspiration that you can use in your existing work. There is also a degree of satisfaction in being able to give back to the community you’ve been a part of for so long.

Another option, which merges public speaker and consultant, is to become a coach or teacher. With sufficient experience and knowledge you could join adult education and teach the younger generation the basics of your trade, or coach people who seek a career in your sector directly. This is just as rewarding as becoming a public speaker, but has a more stable income.


Consultancy is a role that is usually beholden to people in their late careers, simply because it involves giving advice about topics in the industry. You can only give advice if you have great knowledge and experience with the topics involved, and the calm confidence to explain what needs to be done to make improvements. Often, clients would feel doubtful about the advice given by someone that is too young or inexperienced in their opinion, which greatly pushed back the time at which this side career can be started.

The most entrepreneurial of the side jobs, this career also requires a business plan, market research and all the trappings of a company. Usually you will be a sole agent, but it’s also possible to join a consultancy agency as a freelancer or part-timer. Being associated with an agency allows you to benefit from their name and reach, while also giving you some of the protection of an employee while you work. However, you will have less control over how you profile yourself and what clients you accept.

The main benefit of consultancy is that, if done well, it is a very lucrative profession. Management in any company benefits from outside advice, and if you have a good reputation, special insights, or are one of only a few consultants in your sector, you have a lot of work to pick from. Beyond the monetary benefits, successful implementations, projects and consultancy reports also give a big boost to your reputation. This will give you a benefit when applying for high-level executive jobs, especially where risk management and innovation are required.

Consultancy is, however, a competitive field. Many people who lose their jobs without sight of a new job will start a consultancy agency to tide them over, often named after themselves. This tendency has somewhat diminished the reputation of consultants as a whole, and you might need to fight prejudices of consultancy being ineffective, expensive or unnecessary. The key to being a great consultant is to have a strong, clear pitch, proof of your expertise, and to create a plan that makes permanent improvements to the company, even after you’ve stopped your work. A consultant who advises well is worth its weight in silver, but a consultant who can teach their customers to help themselves is worth its weight in gold.

Advocate to a Cause

If you feel strongly about a topic, but there’s a lot of improvements needed, you could become a public supporter of this cause. This is known as an advocate. Causes could include the environment, diversity, peace, specific regions or locations and medicine. But you could also advocate against something, like exploitation, discrimination, eradicating a specific medical condition, misconception or abuse of power.

It is best to be careful not to get too involved with political or religious topics, unless you feel very strongly about that and you are well-versed in the subject matter. Touchy subjects and a volatile audience can cause a minor statement to greatly damage your reputation and career.

Being an advocate is simple put, being in Marketing. You are raising awareness for the issue, seek to sway people’s opinion, and get funding to improve the situation. The methods for this are diverse, ranging from being an author or public speaker, networker, or journalist.

While not supplying any degree of income, becoming an advocate can greatly shore up your reputation, gets you in touch with people, and offers a wealth of experience in managing a brand and funding. As such, it is a great introduction into the world of C-level Executives, Brand Marketing and entrepreneurship. Extensive networking in your desired field to end up in also means you will have greater opportunities in that specific sector. Additionally, an advocate’s position is a natural lead-in to politics, which is a great opportunity but it’s own career as well.

But advocacy also is an ethical profession. Once you walk this route, you need to maintain your reputation or you will not just damage your career, but taint any of the causes you have advocated before. This means that for you, ethics and professional behavior are the top priority when it comes to behavior. You will need a degree of political acumen to navigate the difficult world of fundraisers, capital and investments. People don’t usually give something for nothing, so this career requires great reserve and awareness.


Governance and policy go hand in hand, and a career in politics provides a lot of opportunity to network, learn about the rules that govern financial markets and corporate law, as well as get involved in the governance of your city, region or country. Politics combine all of the previous side careers, but limited to the political agenda that you carry. You will usually be part of a like-minded group in a political party, and can expect great involvement.

But what goes for an advocate goes double for a politician: trust and reputation are your currency, so you need great awareness of people and the system to succeed. You may be in danger if you lack knowledge (of people, law or your party’s agenda) or behavior and lose the trust of the people you are taking part in governing.

Politics by itself represents a career line, and it can quickly come to define you and take up the greatest part of your time. Rewards can be great in terms of exposure and networking, but politicians don’t always earn a lot of money. Rather, once your political career reaches its apex, you can expect to fold back into a new secondary career as an author, public speaker or advocate.


It can be a very worthwhile thing to become a self-employed business person and put your theoretical knowledge and expertise in practice. For example, using your knowledge as an IT architect to start up a business in ready-made solutions, or using your self-developed HR theories for a HRIS software package.

The key elements involved are being able to turn theoretical knowledge into a practical product which can be sold to customers. You need to make a business plan showing that you have a market, how your competition looks, and what you need to make this work. This also comes with a financial sheet explaining what you need in terms of startup money.

In many cases, starting up a company is not that expensive, but you will be under pressure until your company is set up and stabilized. You may need other people to help, which means staff, in turn leading to compliance with all manner of regulations and financial best practices.

In turn, a successful startup can soar quickly and provide a lot of income – but remember that you need to pay taxes, insurances and pension plans. Leading your own company is rewarding, but there are a lot of things involved you will need to know. The more people you hire for specific positions, the less you need to know yourself, so identify your strengths and weaknesses as a Founder and hire accordingly.

Experience in leading a startup and turning it into a full-fledged successful business is a great qualifier for some of the strenuous leadership positions in international management. If you seek a career as a C-level executive in an international company or nonprofit organization, being an entrepreneur will offer you the insights you seek.

Business Facilitator

When you’ve been on a lot of business trips, you learn a lot of things about the world. How to analyze the best hotels, best distances between hotels and office, picking restaurants, language and etiquette. You know the difference between business and economy class, not just in general, but likely the differences per airline company. You know what is essential to bring, the mistakes you made, who to contact.

All this knowledge combines into a specific combination of consultant and entrepreneur: the business facilitator. You could be situated in a business-rich location, and cater to a lot of business people traveling – arranging and supporting them in their business efforts. This is a specific form of business that offers a great balance between contacts, money and reputation. This combines a travel agent with the concierge, and focuses on high-end business people who need their business trips arranged quick, discrete and perfectly.

You could also combine the best practices of hotels, restaurants and meeting venues to create a business center, where people will find anything they need to set up shop, make their deals and promote their business. This usually is bound to one location, and caters to specific business types, such as startups or from certain sectors.

If you are in your mid-career and hoping to break through into higher management, you could do worse than becoming a personal assistant to an influential international leadership figure. You will learn a lot about everyday life in that level of business, the processes and procedures in play, while gaining some mentorship and contacts in the meanwhile. Of course, being a personal assistant is a tough job, requires a good memory and awareness, and knows long hours and very variable levels of reward. But if your career is a 6 right now, and you want to boost it to an 8, consider taking the plunge and stepping in the shadow of the person you’d want to be like.

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