Career advice the Probably Good team would give our younger selves

At Probably Good, our mission is to help more people maximize the impact of their career based on their own values, personal circumstances, and motivations. In the past few months, we’ve made many exciting strides towards fulfilling this mission –  like launching our 1-on-1 advising calls, renovating and rebranding our site, and publishing several new in-depth career profiles and career guide chapters. Though we’re still a relatively new org, we’re learning a lot and striving to create high-quality content for a range of preferences and cause areas (be on the lookout for a whole lot of climate-focused career content in the next month!).

We think this sort of guidance can be extremely helpful in navigating your career search (it’s why we do it!). But we also know that life is complex and unpredictable. Planning and strategizing for your career is super important, but so is chance, failure and learning along the way. 

So to get a bit more personal and strike up some career conversations, our team is sharing the top piece of career advice we’d give our younger selves. We all come from fairly different backgrounds and career stages, so hopefully this can give a more practical perspective on our own career journeys.

Anna Beth, Writer

Show you can do the work instead of relying solely on on-paper qualifications. When looking for a job out of undergrad, I often wouldn’t even apply to ambitious opportunities because I assumed I didn’t have the impressive on-paper qualifications needed to stand-out. This probably has something to do with imposter syndrome, but I actually felt pretty confident in my abilities — I just thought I didn’t have the background needed to be given a chance. Looking back, this was a pretty defeatist outlook. I wish I would have spent more time focused on practicing and sharing the sort of work I wanted to do. When I eventually started sharing (and emphasizing) a portfolio website with mostly personal writing projects, I ended up getting more interviews and my first full-time role. 

If you feel limited by your background or like you’re somehow behind for not doing more while in school, it can go a long way to show – not just tell – you can do the work. Sure, those prestigious internships and achievements could open doors and give you an extra boost, but ultimately, organizations want people who can actually do a good job and have something valuable to offer. Try a do-it-yourself approach by taking up projects that interest you, keeping up with a website, actively seeking work-tasks, or doing more volunteer work in your field. 

Dylan, Researcher

You have more options than you likely realize. We tend to lean towards options we're already familiar with, and the careers we're exposed to at a young age are determined by fairly arbitrary variables like location, educational background, and our parent's careers. I think this means the career goals we form early on are often highly path dependent. In reality, there's far more areas of work we would have been excited about, if only we'd been exposed to them earlier on. 

This probably sounds quite obvious, but it's something I wish I'd internalized before I latched onto the first subject that gripped me then spent a fair few years pursuing it at postgraduate level. I might still have chosen the same route, but my decision would have been better informed had I spent some more time trying a bunch of different things.

Itamar, Head of Growth

Early on, prioritize broadly applicable skills–like learning and communication–that will be useful regardless of what path you end up taking. This is especially beneficial in cases where you’re unsure what you’ll do later, or think that there’s a high likelihood you’ll move between distinctly different roles/fields.

Remember that there’s always an opportunity cost, so you don’t want to waste your time mastering a highly specialized skill that you end up never using again. That said, you can’t always know what skills you’ll need in the future, and there’s nothing wrong with learning some specialized skills when a task calls for it, particularly when you can hone your generalist skills along the way. For example, learning to program in R can help improve your general programming skills, and, more broadly, your general learning skills too.

Omer, Co-Founder & CEO

The roles you take and organizations you work at have a profound impact on your identity. People keep changing and growing throughout their whole life. Being surrounded by certain types of people, immersed in some specific workplace culture, working towards specific goals - this all has a huge effect on who you become. Is your environment pushing you to be a kinder person? One who collaborates or competes? Are you becoming someone who speaks their mind more or learns to go with the flow? There are countless small ways in which you will be different after a few years, including what sort of person you want to become.

At one of the points that I was considering a major career change, a manager I admired asked me: “Do you want to become the person that this job will push you to be?”

The answer can be both positive and negative (or neither), but, especially for early career professionals, I think it’s an important (and sometimes neglected) consideration when deciding on a career path.

Sella, Co-Founder & Head of Research

Be more proactive in reaching out and pursuing opportunities. My default approach is to learn, read, strategize – but not reach out. In hindsight I’ve been shocked by how many of the people I admire are happy to engage and provide advice or opportunities when young people reach out, and how many of my heroes started their own path by reaching out to those they looked up to. I think a similar lesson applies to trying to pursue opportunities more broadly – like that job you probably won’t get or that fellowship that’s hard to get into. 

Of course, reaching out also needs to be done well. If you’re contacting a person or organization you look up to, you should be respectful of their time. You should invest in reading their available work to identify where they can be most helpful (or better yet, how you could be helpful to them), and write extremely succinctly so they don’t need to spend much time to decide whether they want to prioritize engaging or not. This approach also leads to way more failures and rejections than the passive approach, but the occasional successes are very much worth it.

Thane, Operations Lead

Regardless of where you’re at in your career, reevaluate your options before making big decisions. Ideally I would have had the kind of advice we provide at Probably Good while I was in high school, or when I decided to switch majors at university, and would have known about many more impactful careers early on. But I actually could have benefited most from exploring my options a few years into my career once I decided to pursue something more impactful. 

At the time, I felt like I had fewer options and even less time than I did at university, because I’d already ‘wasted’ years of my career. So it was easy to jump straight to job applications rather than stopping first and figuring out what paths were really available to me. Thankfully what I pursued turned out to be a great fit, but in retrospect, that was lucky. I have a feeling that this happens a lot, whether by prematurely fixating on a job or career, or by continuing to follow a previously made career plan. Regardless of your situation, if you’re about to make a big career decision, the time you put into reevaluating your options will always be worth it, because you’ll either uncover new paths or be more certain of your current career trajectory. 

Vaishnav, 1:1 Advising Lead

Be strategic about your weaknesses. Over the past few years, I’ve learnt to factor in my relative strengths and weaknesses while choosing roles and organizations. Conventional wisdom and our negativity bias can often lead to a relentless focus on weaknesses. However, it’s worth being strategic about which weaknesses to work on while prioritizing skills that are a better fit for your temperament and personality. 

For instance, my challenges with organization and attention to detail stood out as areas of consistent feedback in my early career. I took steps to improve these skills, striving for a level of competence that wouldn't impede my professional growth. However, I got a lot more “bang for my buck” by pivoting towards roles where these attributes weren't the primary evaluation metrics ( eg. transitioning from a compliance and process heavy role at a big bank to a fundraising role at a startup). It's also useful to keep in mind that some skills seem way more salient for early career roles and are relatively less valued as you progress. Moreover, it’s worth considering the explicit opportunity cost of focussing on weaknesses since even skills that draw on our natural strengths often need a great deal of cultivation and refinement. 

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If you have an interesting piece of career advice you’d give your younger self, feel free to leave a comment! Or if you find yourself in an earlier stage – still exploring options, applying to opportunities, or wanting to make a big career change – we encourage you to apply for a 1-on-1 advising call or explore our content for articles that interest you. You can also contact us if you have suggestions or ideas for career-related content you’d like to see more of.