How to Apply for Jobs If You Have a Confusing Work History

Not everyone knows what they want to be when they grow up, and that's OK.
Alessandro Pilo
Budapest, HU
June 8, 2021, 9:32am
Illustration of a man crouched underneath a desk as emails and notification sounds come out of his laptop which is on fire.
Illustration: Oqvector via AdobeStock.

This article originally appeared on VICE Italy.

My career path has not been the most straightforward. After completing a PhD in Literature in Italy, I decided to move abroad and work for an environmental NGO. Later on, I worked as a cook in a vegan bistro, an environmental education teacher and a hostel receptionist.

I could go on and on, but you get the picture. For years, I only cared about following my interests and developing multiple skills without considering how that would affect my future career prospects. But lately, I’ve been watching friends reap the benefits of their loyalty to a company or a specific field, and wondering if I made the right choice.

Contrary to what I’ve been told my whole life, not everyone agrees with the idea that we should all pick a career at an early age and stick with it. For instance, Canadian author Emilie Wapnick thinks some people simply don’t have a true calling in life, but they might have a variety of equally valuable talents and interests. She calls this group of people “multipotentialites” and includes herself in the group. Although often discouraged from pursuing their passions based on society’s antiquated and inflexible notions of work, multipotentialites can only achieve their full potential when they take advantage of varied opportunities.

Perhaps, as argued in the 2019 book Range by investigative reporter David Epstein, being well-versed in multiple fields is actually more important in today’s society than following a narrow specialism. If the pandemic showed us anything, it is that devoting your whole career to one specific sector – say, catering – can’t always guarantee you’ll have financial stability for the rest of your life.


In any case, the reality is that, in today’s job market, my fragmented work experience simply doesn’t look great on my CV in the eyes of recruiters. So I talked to two specialists about how people like me, who’ve hopped around various jobs and industries, can make the most of their job applications. 

"Let’s dispel a myth,” said Olimpia Ricci, a Bologna-based recruiter and headhunter. “Very few people go straight from point A to point B [in their career], and even fewer people grow up with a ‘calling’ for a specific job.”

Whether you’ve been switching roles by choice or by necessity, Ricci said there’s no use in trying to hide it in your application. “You should build effective storytelling around it,” she said. “You should create a common thread linking these experiences in your CV and cover letter, a narrative that can convince me you are the ideal candidate for the position because of your diverse experiences.”

Guido Penta, an HR manager based in Rome, agreed with Ricci – but he also confirmed my hunch that CVs displaying a fragmented professional history tend to be overlooked. “A CV barely tells you 30 percent about someone’s experience, but recruiters get so many of them they don’t have the actual time to thoroughly look into every single application,” he said. That’s why some HR managers might play it safe and just go for a more traditional profile. 

To increase your chances of being invited to an interview, Penta said you should pare down your experience and really tailor what you include to the job you’re applying to. “If you start from a ‘disadvantaged’ position, your CV and cover letter must be impeccable and reasoned,” he said. You can also bring up relevant work experience you’ve initially omitted from your resume during the interview phase, where you have more time to explain your employment history and motivations.

Penta also said the main red flag recruiters look out for is if you’ve changed jobs many times within one sector. That could suggest that you’re difficult to work with and you’ve been fired by multiple employers, or that you might be in it only for the money, ready to jump ship as soon as you’re offered a better opportunity. 

If your problem is that you want to settle into a job for a longer period of time but can’t find something that keeps you interested, Ricci said you should look into roles requiring you to wear many hats. For instance, you might be tempted to join a big-name corporation, but working in that setting often means specialising in a narrow role and developing your career vertically, by managing people in your department, for instance. But your multifaceted experience and abilities will likely be valued more in a smaller businesses, where you’ll probably be asked to do a bit of everything.

If you’re really not sure if a job works for you, Ricci said you shouldn’t be shy about using LinkedIn to contact current or former employees. “Ask them the pros and cons [of the job or the company], and your questions,” she said. “That social network exists precisely for that reason.”

Finally, if you are currently feeling stuck, you should take a minute to reflect on why that might be happening before jumping in to the application process. “If you have no career prospects and your work is monotonous, it is natural to feel oppressed,” Penta said. “But if you are the kind of person who gets easily bored, I'll be a bit brutal and say that changing jobs will not solve the problem.”