The Five Pillars of Work: How To Feel Safe Without A Job

On money, security, and rebuilding safety in a portfolio career.

It’s not about the money.

The number one reason people give for hesitating to leave a job is money. As I’ve been unpacking my five pillars of work framework to support people to move toward a portfolio career, this is the final pillar: money. In the countless conversations I’ve had over the past year about self-employment, it was the dominating factor for staying in a job, taking no risks, and ‘playing it safe’. If you ask people, “Would you still do your job if you won the lottery?” the answer is usually no.

But is it really about money itself? I’ve noticed that money anxiety doesn’t track particularly well with actual numbers. Not only people who don’t have a lot of money worry about it, it’s also people who objectively have plenty. A friend of mine has millions in the bank and still worries about money. Another one, who has never really had money and has almost no savings, is the most chilled about it. So, if you look at it objectively, money anxiety often doesn’t make much sense.

As Morgan Housel writes in his book The Psychology of Money, we all go through life anchored to a set of beliefs about how money works and those beliefs vary wildly from person to person. People raised in different families, generations, and economies learn very different lessons. What seems crazy to you might make perfect sense to me. So equally smart people can completely disagree on how you should earn, spend, invest your money or how much risk you should take.

So, in most cases, it’s not actually about the money itself but the underlying psychology. About the stories we tell ourselves about safety, risk and success. We often treat money as a proxy for security.

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External security vs. internal safety.

So let’s look more closely at security. A distinction that helped in my train of thought is separating security (external) from safety (internal).

External security can take many forms: money in the bank, a job providing stable income, supportive parents, a partner’s income, or a country’s social safety net. All of them do the same thing psychologically: they absorb risk for you.

Internal safety, in contrast, is the feeling that whatever happens, you’ll be able to handle it. It is felt in the body, regulated in the nervous system and built through experience. It lives in your skills, your adaptability, your relationships, your sense of agency and your ability to respond to uncertainty.

Most of our systems such as education, work, and social institutions, are very good at providing external security but not at teaching us internal safety. Over time, we learn to optimise for predictability, compliance, and stability. We’ve learned to outsource security and risk. We learned to feel safe when someone else is in charge and to treat uncertainty as something to avoid.

So, money creates security, but not necessarily a feeling of safety. Which is why:

• people with high savings can still feel anxious about money

• people with unstable income can feel calm

• and why leaving a job can feel terrifying even when the numbers work

So what role does a job play in all of this and what breaks in terms of money and security if we leave it to become self-employed?

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The job as a security container.

If you’re employed with a company, security comes in a neat package that is a fixed salary, benefits, and a pension plan promising stability and predictability. Your financial safety is outsourced to the company and as long as you stay employed, money is steady and your needs are covered. The underlying belief is simple and deeply ingrained: security comes from being employed.

So leaving a job and leaping into self-employment means leaving this security behind which triggers many of the core scripts our system has trained us for so long. Safety comes from predictability. Stability equals survival. Uncertainty is dangerous. Security must be locked in. Risk is something to avoid. This can cause anxiety and lead to fear-based rather than intentional decisions when designing a new work life. People might behave in ways that actually undermine their own goals.

Overcommitting to short-term paid work at the expense of long-term goals is a common one. (“I technically have like four jobs now and not enough time to focus on my own things”). Recreating income quickly feels safer than sitting with uncertainty even if it actually rebuilds the same constraints of a job that people were trying to leave.

Few people actually have a clear definition of what ‘enough’ means and remain geared toward limitless growth and earning. (“By accepting all three opportunities, I could double my previous salary”). Opportunities stack not because they’re aligned, but because they promise relief. What looks like ambition is often an unexamined attempt to secure safety through more.

Others have just started a family and the provider script runs deep (“With my kids, I just cannot afford two years of lower income”). Beneath it sits a familiar belief: that employment is the only responsible way to create security and that anything else is an unnecessary risk, regardless of how the numbers actually look.

Many react to uncertainty by trying to avoid any dip at all. Even temporary fluctuations in income can feel like failure rather than part of a transition. Short-term drops are treated as danger signals, pushing people to optimise for immediacy instead of sustainability.

Having looked at how security behaves in employment and the anxiety it can trigger during transitions, let’s ask the uncomfortable question: does employment still equal security in today’s world?

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Is employment really security?

One of our most deeply ingrained beliefs is that security comes from being employed. For a long time, a stable job, a steady salary, a contract has been the default answer to uncertainty. But is that still true in today’s world?

I think it’s increasingly a false sense of security. Employment-based security can disappear overnight: through layoffs, company collapse, entire industries vanishing, or roles being automated away by AI. This is only going to be accelerated in the next years. In a world where jobs are being disrupted and things change faster than we can keep up with, does it still make sense to outsource security to a single full-time job? Is it even still possible to optimize for stability and predictability? When a job goes, all of the security tied to it goes with it at once. Isn’t that actually kind of risky?

What’s striking is how differently we think about risk in other areas of life. When we invest, we know better than to put all our eggs in one basket. We diversify. We spread risk. We accept that some things won’t work out and that resilience comes from not depending on a single outcome.

When it comes to work, however, we often do the opposite. We place almost everything on one card and call it the safest option.

In her book ‘The Ten Permissions’, Jill Reilly argues: “You’re better off detaching your sense of security from any single company, contract, role, or position and attaching it to yourself.”

I agree. The world is changing fast, and our mental models about security haven’t caught up yet. If security is no longer guaranteed by structures, we need to learn how to build it in ways that can move with us.

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Building security and safety in a portfolio career.

Portfolio careers might be a pragmatic response to restructure risk and security in a way that fits today’s reality. By diversifying work across multiple sources, people become less dependent on a single employer, more resilient to change and better able to adapt as industries shift.

A portfolio career doesn’t ask you to be reckless. You can combine stable income streams with more exploratory work. A part-time or fractional role, a freelance or consulting project, writing work here and there, and a creative experiment that might slowly grow into core work. It’s a pragmatic way to experiment, building skills, confidence, and optionality as you go.

How do I rebuild security without recreating the job I just left?

I’ll share some of the strategies that helped me take the first steps toward a portfolio career, work through my security scripts, and avoid some of the traps I described above.

1: Create a floor: this is the foundation of security

Most people never clearly define their ‘enough’. Instead, they default to maximising income as quickly as possible. If I can close more work, I should, right? Leaving money on the table feels irresponsible. What often goes unnoticed is that by not leaving money on the table, we end up leaving other things there instead.

Start by clarifying what security means for you. Define a monthly baseline for a defined transition period (e.g rent, living costs, and a few simple comforts for 2026). This number becomes your anchor. It allows you to decide how much stable, part-time, fractional, or consulting work is actually useful and just as importantly, how much is not. In practice, this can start as simply as reducing a full-time role to three or four days a week.

It is where compromise becomes intentional. You choose stable work to cover the floor. And you deliberately protect the rest of your time for experimentation, creative work, skill development, and working toward your longer-term goals.

2: Legitimize the change: create a feeling of safety

I recently read an article by Paul Millerd about leap capital that I really enjoyed. Leap capital is a specific quantity of money (e.g. baseline, savings, net worth, runway) and an accompanying story that someone uses to convince themselves that it is reasonable to make a change in their work life.

While the monthly baseline above can already be part of that leap capital, I think the accompanying narrative is just as important. It’s the feeling of safety that the story creates: I’m not being completely reckless. I too needed a story that allowed me to step away from paid work and made risk feel responsible to me. In my case, that story was ‘investing in myself’: time for personal growth, learning, creating space to think.

3: Upgrading our scripts about security: moving safety inward

As explained above, most of us carry deeply ingrained scripts about security and unless we work with them during the transition, they keep running the show in the background. At its core, this is identity work and I’ve written about this in depth here.

Security scripts don’t change because we decide they should. They change over time through awareness, small interruptions, and collecting new evidence. We notice the scripts we’re running (awareness), experiment with acting differently (behavior change), and let reality respond (evidence collection). Evidence could look like this:

• experiencing uncertainty and surviving it

• earning income outside of a salary for the first time

• making your own decisions and seeing it work out well

• losing structures and rebuilding them in a better way

Over time, and with repetition, these experiences start to stack. It is the nervous system slowly learning that the old rule is no longer universally true. We build new mental models through acting differently long enough that thinking follows.

4: Redefine success: so money isn’t the only safety signal

If money is the only success metric we track, any temporary dip will feel like danger. Even if it’s part of a transition, anxiety kicks in and our security efforts collapse back into short-term optimisation. To avoid this trap, we need to expand our definition of success beyond money. That means asking a simple but uncomfortable question: What does success look like if I define it myself?

Instead of maximising income at all costs, success might be steady enough income. It might be flexibility, meaningful work, aligned collaborations, excitement or things outside work such as quality time with loved ones. I’ve written about this more extensively in the Vision pillar, but the core idea is simple: when you know what you’re optimising for, you’re less likely to panic when the money metric fluctuates.

5: Ever-evolving portfolio career: security through diversification and adaptability

In a portfolio career, we can create security by diversifying our income streams across multiple sources of work. Not all at once, but you’ll build your income streams sequentially and rebalance them over time. Portfolio careers aren’t meant to be fixed. They’re meant to evolve throughout life. Components are added, paused, or dropped as your interests, capacity, and circumstances change.

Your feeling of safety doesn’t come from any single component working forever. It comes from knowing the system can change without collapsing. From having more than one way to earn, contribute, and adapt. And from you being the one in charge of that.

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Building internal safety over time

Years ago, my husband told me he didn’t understand why people would consider employment safer than entrepreneurship. He said “I feel safe because I know that I can create opportunities myself and make them a reality without depending on the job market.”

At the time, I laughed it off. I was in full-time employment and not ready to have my way of thinking challenged. I dismissed it as ‘he’s just different from me’. There are people for entrepreneurship, and people for employment. And I’m certainly not entrepreneurship material.

Over the course of my own journey, from corporate to start-ups to self-employment, my perspective has changed. I had to confront everything that I’ve described in this article. Experienced every single script and limiting belief. And only in hindsight did I really understand what he was pointing at back then.

Now, I’ve built the confidence in my skills. Even better, I know that I can learn anything if I want to. I know I can build things from scratch and offer them to the world. I know I can adapt when circumstances change. I’ve built relationships that can catch me if I fall. I’m far more comfortable with uncertainty and with taking calculated risks.

After all, I also feel safer to know that I do not depend on the job market out there. Over time, I’ve slowly learned to build internal safety. And now I know, that you can, too.

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📚 Read the full Five Pillars of Work series:

• The Five Pillars of Work: How To Transition From A Job To A Portfolio Career

• The Five Pillars of Work: Rebuilding Vision from the Inside Out

• The Five Pillars of Work: How To Structure Your Days When No One Tells You How

• The Five Pillars of Work: The Hidden Identity Crisis of Portfolio Careers

• The Five Pillars of Work: How To Feel Safe Without A Job (this one!)

• The Five Pillars of Work: The Power of Intentional Community Building

About Afterwork.

I’m building Afterwork to help people navigate the biggest shift of our time as AI disrupts work as we know it. I write about what comes next - from portfolio careers to deeper questions of identity, purpose, and life beyond employment.

Through my mentoring, I work 1:1 with professionals transitioning from jobs into portfolio careers.