What Is “Career Cushioning” – And Should You Be Doing It?

It’s okay to keep your options open if you’re not happy in your current job. Here’s how.

By Melissa Wong        6 October 2023

“Career cushioning” is a relatively new term. Simply put, it means planning for an alternate job in case your current one doesn’t work out or you decide that you want a better one down the road. It means coming up with a Plan B to “cushion the blow” should something unexpected happen to your current job.

There are many ways to “career cushion”, from keeping your resume up to date and upskilling to applying to other companies while you’re still employed, so that you’ll be ready to move on to a new job when the opportunity presents itself.

Sandra Quelle, founder and principal career coach at The Happy Mondays Co., a career consultancy, explains how to “career cushion” the right way.

Q: Why might someone choose to “career cushion”?

Sandra: Today’s job market is so fast-paced and competitive that many professionals are adopting this approach to safeguard their career prospects.

When a client brings up the subject, we see it as an opportunity to understand their reasons for shopping around. From our experience, one doesn’t just wake up one day and decide to shop around for a new job. Talking to a career coach or even some honest self-reflection will allow you to identify your push factors, any underlying fears, threats, or feelings of unreadiness or unpreparedness.

Crystallising the causes will help you come up with an action plan, putting you in a proactive, rather than reactive, position. In other words, it builds career resilience. For some people, this reflection allows them to see that there is hope in their organisation and thus, they may decide to talk to their boss to help them gain alignment. Other times, it shows them that their time in the business is over and they need to gear up for a change.

How do you build career resilience? This might include updating your resume and personal pitch to highlight the skills and personal characteristics most valued for your target role, leveraging your LinkedIn account to support your interest and readiness for the target role as well as to find key people to connect with, and ultimately, connecting and networking with professionals in your target industry and job scope.

Q: Is it wrong to “shop around” for a new job while still in your current one?

Sandra: It’s a fine line between career cushioning with integrity and fishing around. There are benefits to exploring job opportunities while still employed, but it’s important to do it ethically.

Networking can help you keep a pulse on the market, gain insights and stay informed about your own market value. However, attending interviews without intending to change can, at a macro level, have a detrimental effect (although some would argue that this could give you an understanding of your market value). After all, it signals to employers that they have a greater variety of candidates to choose from, which negatively impacts the negotiation power and salary from the candidates.

You’re also wasting the interviewer’s time by doing this. Companies keep track of candidates who abandon the interview process or reject offers, as well as the number of times a candidate has applied to their company. Singapore is a small market; wasting a company’s time could also jeopardise your chance of securing a role at that company in the future.

In general, we don’t recommend shopping around in this way, but there are a few exceptions where we have encouraged people to do so:

  • If they sense that their company might make them redundant or they perceive that the company is changing direction in a way that they don’t agree with. 
  • If they feel trapped in their current organisation (“I don’t like it here but I can’t leave because I don’t think anyone else would take me”) and need to gain a sense of self-worth and hope. 
  • If they are searching for a job and want to brush up on their interview skills before going for their dream job.

Before going to interviews, it’s worth reflecting on the potential risks and benefits associated with the decision. For instance, if your bosses find out, they may become mistrusting of you, and this may affect your future prospects in the company, particularly if they feel you’ve been well-treated all these years. On the other hand, they may worry about losing you and offer you extra incentives to stay.

Q: How can we tell whether it’s time to leave our job because we feel we deserve better, as opposed to just being bored with it?

Sandra: Some questions to ask yourself: How do you feel on Sunday nights? How often do you talk about your work? How do you feel when you talk about your work? How often do you say “I should/I have to/I need to” versus “I want to”? Are you playing to your strengths? Do you feel you’re leveraging your potential?

It’s important to answer those questions honestly. More often than not, the people who seek us out for career strategy and coaching often reply with, “I don’t feel fulfilled”, “I dread going in”, “I’m confused” and “I’m burnt out”.

That’s where a career coach can help.

We work through the underlying reason for change in the first place. Often, our reaction is to change something, but that doesn’t always fix the feeling of boredom or feeling unfulfilled. These cues are simply indicators that something is not right.

Unless you dig deeper to understand the root cause and draft a plan to address them (and yes, part of that can be to find a new job), the problem will continue even in your new job.

“But I deserve better!” is something I hear a lot, and that’s great. But you should also ask yourself what “better” looks like. Is it defined or is it an elusive thing that you can’t quite put your finger on? Visualising and articulating your ideal scenario is the first step to working towards it. 

Q: Can you suggest a few ways to upskill while working full-time?

Sandra: One of the easiest ways to upskill is by following emerging industry trends – for example, utilising AI applications within your specific industry and domain.

A practical approach to upskilling might start with analysing your skills. This involves comparing the requirements of the roles you aspire to with your current experience and skills. In doing so, you can identify your strengths and the areas that need improvement. This process mirrors what you’d do when assessing if you’re ready for the role.

This skill analysis exercise allows you to pinpoint the gaps in knowledge and experience, which may include a lack of specific industry knowledge or a lack of experience in certain areas, for instance. Once the gaps are identified, it’s time to create a comprehensive action plan to address them effectively.

Addressing skill gaps may not always require pursuing a formal degree. Instead, doing short courses, attending relevant events, networking within specific sectors, seeking stretch assignments at work, secondments, or shadowing opportunities can all be valuable ways to gain the necessary knowledge and exposure.

Aside from attending courses, find out more ways you can upskill.

Q: Is it okay to tell your current boss that you’re “putting yourself out there”, even if you’re not sure you want to resign yet or not?

Sandra: It depends on your relationship with your current boss and the trust level between the two of you. If you fear that your boss might isolate you or find an excuse to fire you, then don’t. Protect yourself. If you’re looking outwards to find a new role, chances are it’s because something isn’t quite working where you are.

If you choose to share this information with your boss, how you approach the conversation is important. What are you seeking? If it’s an opportunity to grow, are you willing to grow within your current organisation or have you already decided that it’s not a good fit?

If you’re able to grow in your workplace, allow your boss and the organisation a chance to meet your needs. This is a great option if you’d like to stay within the business and can trust your boss to take that information on with everyone’s best interests in mind.

If they can’t match your needs internally, they may help connect you with others who can, and this may be the catalyst to helping you find your next opportunity. It’s not the most common thing – it depends on your boss’ response and work candour – but I’ve seen it happen.

Q: What are some signs that your current company may fold in the near future or that management is unstable?

Sandra: Some external factors to look out for are industry growth (is it slowing down or in a boom period?), economic recession, or consistent reduction in clients. A strong company is usually one that walks the talk and has a positive vibe. You can feel it in the way the employees talk about their work, how they share on social media, or when you go to interviews.

Early indicators of a poor performing company are: Indecision, constant swings on priorities, lack of information sharing, too much change at the top, high turnaround of staff at all levels, gossip, and negative comments or energy from those who are demotivated.

Other typical business indicators include reduced benefits, budget cuts, restructuring or downsizing. If you’re concerned about your current company’s stability, stay informed, seek transparency, assess your options, and take proactive steps before actions are forced as a reaction.

Looking to make a career change? Here’s what you should know before taking the leap. 

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