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Can You—And Would You—Secretly Keep Two Jobs?

By News Creatives Authors , in Leadership , at August 22, 2021

Wall Street Journal contributor Rachel Feintzeig recently wrote about people having “secret lives” holding two jobs, where neither employer knows about the other. She carried out interviews with six anonymous workers secretly working two full-time jobs, noting that the pandemic “has given us new opportunities to shirk and fib.”

She found a software engineer who claimed he was only logging in three to 10 hours of productive work in his first job, and now making “incredible money” from two jobs. All he claimed to be lost were unnecessary meetings in the first job. Another tech worker took advantage of his company’s generous Paid Time Off policy to start another gig. Along the way, he has learned to politely say “Sorry, not enough bandwidth” to colleagues requesting meeting time.

A woman who started working two jobs after Covid-19 arrived received an email from one of them outlining a return-to-the-office plan. She gave in her notice, landed a different second job, and hired a personal assistant to help her keep track. A bank employee sent home to work seized the moment to take on three other employers, then left the bank for full-time work with one of those employers – along with permission to take on additional gigs.

Feintzeig also provided a guide on “How to Live a Double (Work) Life,” (not included in the online edition of the article) with pointers including a) find one job with an older company not up to speed in managing remote workers, b) avoid startups (they ask too much) c) look visible (like leaving your MS Teams light on green) d) master which meetings to take, e) stay under the radar (e.g. by tapping LinkedIn’s privacy settings) and f) resist overwork (by dropping overly demanding jobs and taking time for yourself).

What to make of this secret two-jobs phenomenon, and the advice on how to live with it? Consider the guide as a thought experiment – as Feintzeig may have meant it. Ask yourself:

Is secretly taking on more than one job an acceptable long-term arrangement?

Absolutely not! It goes against to core idea of career ownership, which is to stand up for what you want to do and communicate that to your employers. It also goes against an ideal of “talent liberation” that seeks to shake off restrictive employer assumptions about what you ought to be doing with your career. This does not mean to deny you discretion about what you share with any single employer about other work arrangements. Confidentiality agreements can be helpful to both parties here.

Can having two secret jobs at one time provide a temporary solution?

Quite possibly, yes. You may be in a difficult financial situation through no fault of your own, or be stuck with family medical bills, or rental fees, where the additional income is critical for staying afloat. In this situation, be clear in your own mind what you are offering each employer, and what to say if challenged. Also, work toward what at least one of Feintzeig’s examples did. That is, have one main job and let them know you will deliver value while at the same time having other gigs.

Is there a title for the kind of multiple-job career you may prefer?

There is indeed a title, and it’s the highly respectable title of a portfolio worker. Business management guru Charles Handy came up with the term in 1989, years before the web, email and more recently online conferencing have come along to support this kind of work. A portfolio worker maintains a range of different work assignments at any one time, living and learning through the mix of assignments to maintain employability and to manage your own career in a sustainable way. Your reputation earned from past and present jobs is the key to your career future.

Is having a trusting relationship with one employer too much to ask?

It depends what you kind of trust you want. Can you assume your present employer will still be around at the end of your career? Probably not. Can you assume your employer has your career interests at heart? Only if your employer does not practice the kind of top-down talent management strategy—driven by company strategy—that has been popularized over the past 20 years. However, you can hope for regular two-way “career conversations,” where you and your employer discuss your separate evolving agendas and maintain a shared understanding of those agendas.

Was it wrong to grow up expecting my employer to determine my career?

Welcome to the club! Many people grew up being told to expect that. However, the evidence over the past 30 years is that lifetime employment can stifle innovation, and constrain both parties to an employment contract. Also, employment statistics across the developed world suggest you will work for an average of six or more employers over your career. Even if your employer wants to promote lifetime employment, they are not in any financial position to ensure it. In today’s world, you must own your career.


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