Should you do what you love? (And other career strategies)

As an educated and career driven 20-something, I think about my job and my career quite often. Since I’m surrounded by friends and colleagues who are similar, our discussions naturally gravitate towards work and career related topics. One topic that comes up in particular is how to choose the right job and career.

Many of my generation have been told to “Do what we love.” While there are plenty of people who follow this strategy there are plenty who don’t. It works for some people, but not for others. Fortunately, doing what you love is not the only right career strategy. So for people who don’t like this strategy, don’t know what they love, or are just struggling to proceed, how do you know how to choose the right job?

Through my many conversations with my friends and colleagues, I’ve come up with a few common strategies for choosing a job or career, along with some cautions and steps for success. I’m sure there are others, but these are the ones that seem to stand out.


TLDR: I don’t have all the answers, and I don’t believe there is a silver bullet, but I think these strategies and subsequent thoughts will help others work towards finding a path that is best for them.



Strategy 1: Do something you love

Background: A common phrase we hear in society today. If we take a job or career we love, we’ll commit ourselves fully and deeply engage with the work we do. A phrase we often hear is “find a job you love and you’ll never feel like you worked a day in your life.” And working a job that you love and getting paid to do it – Who wouldn’t want that?


Reality Check

Unfortunately, not everything we love is directly translatable into a job or career. Furthermore, not everything we love pays a salary/wage that enables us to live at the lifestyle we desire. Finally, not everyone has the means or opportunity to truly do what we love. We live in a world with constraints (financial, educational, experience etc.) and sometimes those constraints permit people from following this mantra.


How to Succeed: Take a shot of courage and rock on. Be relentless on how you prioritize your time. Don’t forget to take care of yourself (physically and mentally)



Doing something you love often gets the connotation that it will be rainbows and butterflies at all times. In reality, that’s not the case. With any job or career, there will be tough times and difficult moments, but for those who are truly doing what they love those difficult moments will be worth working through because it truly is worthwhile. Finally, doing something you love means knowing what you love. While some people know this, not everyone does, especially in your mid-20’s.


Strategy 2: Do something that enables you to do something that you love

Background: The classic means to an end strategy can help people balance both work and play. Work is a big portion of your life, but does not necessarily define all of who you are. For those who follow this strategy, they may not have a job or career they love, but they recognize it provides them with something worthwhile to do for the majority of the week while also enabling them to tackle other more meaningful pursuits.

Reality Check

It may not be fun coming to work every day. It also can get really easy to get comfortable with a particular lifestyle which sometimes locks you into a job you may not like but you need. Without a deep emotional connection to you work, it can be hard to stay engaged for long periods of time or through challenging moments. You also may get envious of those who seem to be super excited about what they do each and every day. Finally, while work and life do not have to be tied to one another, how you are in your life is impacted by what happens at work. For instance, you may take a particular job so you can support your family (what you love) but if you’re stressed or unhappy at work it’s likely it will carry over to how you are at home.


How to Succeed

Find ways to engage and focus at work as much as you can, especially during mundane or difficult periods of work. When you aren’t working, be sure to truly enjoy and make the most of whatever else you are spending your time on. Accept that fact that you might not love what you do, but that you truly love and appreciate the other areas of your life that are really special.



You may not love your job, but following this strategy can give you a well-rounded and balanced life. Some try to separate work and life, but its important to be aware that one can easily impact the other. You’ll want to be mindful of this so you can make the most out of the time you have when you’re pursuing your interests, hobbies, etc.



Strategy 3: Do something you are good at


Pursuing a job or career in something we’re good at allows us to leverage our strengths. It helps us develop our personal brand, which leads to growth and opportunity. When you are good at something, people, and opportunities will follow. When we like what we are good at, and align a job to that strength, it can lead to fulfillment and enjoyment.

Reality Check:

Just because we’re good at something doesn’t mean we want it to be our job or career. Furthermore, not all of our strengths are directly translatable into jobs and careers. For people looking for variety and challenge getting pigeon holed into a specific job is a real concern. However, if you happen to find a job that enables you to use your strengths it can be very rewarding, for yourself and your company.


How to Succeed:

Take stock of your strengths and look to match them with a job or career that fits those strengths. Prevent being pigeon-holed by continuously developing those strengths and picking up new ones.



When you find a job that enables you to use your strengths, there’s lots of potential and opportunity. This strategy favors the self-aware and self-starters who truly understand their gifts and talents. There are lots of things we are good at that don’t necessarily translate into jobs, but if you can find one that does you have a great opportunity.


Strategy 4: Do something that has a need


For this strategy, it’s about going where there is a need. When there is a shortage, there’s often opportunity – whether its in the form of a job, career, or in some cases, a job or career that comes with handsome compensation, following this strategy opens exciting new doors. Pursuing a need often means solving an unsolved problem.


Reality Check:

Just because there is a need for something doesn’t mean that it’s something that’s a fit for you. Perhaps you don’t have the requisite skills or training to do the particular job. There’s a need for Software Devs/Engs’ but if you don’t know how to code it probably won’t serve you well to follow that path.

How to Succeed:

Before jumping into something, evaluate whether the need is fleeting or more temporary. Furthermore, you’ll also want to evaluate whether or not you have the current skillset for whatever you’re considering and what else you would need to adequately pursue a particular job or career.


Following needs presents exciting career opportunities. Taking a job that fits a really big need could enable you to make a significant and meaningful impact. Not all needs will be interesting, so if you do go down this route you’ll want to make sure its worthwhile to you

How to conduct a meaningful informational interview

Over the past few weeks, I’ve conducted numerous informational interviews with undergraduate and graduate students. I enjoy these interviews and welcome the opportunity to talk to students about their career ideas and aspirations. These students are looking for information that will hopefully inform them of whether or not to pursue a potential career, so being able to share insights and stories that can guide them in this process is something I enjoy and welcome.

Last week, I was speaking with a friend who also had done a fair share of informational interviews when they asked me what I thought were the ingredients of a good informational interview. I thought about the many interviews I’ve conducted as an interviewer and interviewee, and came up with a few characteristics.


Diligence – Informational interviews are great learning opportunities, but not all questions are best suited for an informational interview. It’s not very valuable for either of us if they ask me questions that can be found on the website.

I respect the people who take the time to do some homework before the interview. Sure – you can’t know everything about the industry or my computer (if you did, you wouldn’t have any use for the  interview!) doing some prep work demonstrates that you value time. To me, that is a sign of respect.

Furthermore, it also shows that you’re putting in effort to really learn as much as you can, not only on the call but also, before and afterward. That investment of time makes someone want to do what they can to help the other person in their pursuit.

Curiosity – I really appreciate and value people who demonstrate curiosity and inquisitiveness. As the saying goes, “those who are interested are interesting.”

Curiosity often breeds interesting questions, thoughtful comments, and a memorable conversation. It also demonstrates a genuine eagerness for learning, which is something I both respect and appreciate. People who are interesting (in a good way) will always be more memorable, especially when it comes to remembering whom to refer for potential interviews.


Authenticity – I’ve found the best informational interviews are the ones that are ones that are natural easy-going conversations. Sometimes, I think we get caught up in the formality and professional nature of the discussion that we forget to be ourselves.

Instead of telling stories about our background, we explain key bullet points on our resume. Instead of letting the discussion unfold naturally, we stick to our bulleted list of questions we thought of in advance.

There is an art and a science that comes to an informational interview. Diligence and preparedness take care of the science, but curiosity and truly being your authentic-self take care of the art.

There’s no one right way to conduct an informational interview. Like anything, experience and timing (and perhaps a few mistakes) refines our craft. In your next informational interview, try focusing on these three things and see what you learn.

One question to ask yourself before you quit your job

Over the course of my career I’ve had lots of conversations with friends and colleagues who are interested in leaving their job. As an eternal optimist, I usually try to advocate for people to exhaust their means before pulling the plug in hopes that things turn around. However, we all have our own threshold and once it’s broken there’s no turning back.

Last week, I was speaking with a friend who was in a tough position at work and contemplating whether or not to leave for another opportunity. This was not our first discussion on this topic – We had actually had a similar conversation two years ago. Given that this was not their first rodeo, I walked through my usual list of questions such as:

  • What don’t you like?
  • What’s making you unhappy?
  • What could turn this around?

My final question was this: If you were to walk away, what would you miss most, and how would that make you feel? After mulling it over for an evening, the person emailed me back and told me that even though things weren’t great right now, they weren’t willing to give up some of the core things that were valuable to them in their current job. As such, they decided to stick it out for a few more months.

Sometimes it’s not about what the next job offers that is exponentially better than what you’re current situation offers, but rather, it’s about what you’d have to give up if you chose to leave. For people that have exhausted every opportunity and are ready to move on, a new opportunity could be exactly what’s needed. But for others, reframing the question to not what you’ll get but what you’ll have to give up might help you think through if you’re truly ready to move onto the next gig.

While the grass may seem greener, sometimes its not about the greener grass, but focusing on the grass you’re on. To illustrate this point, I’d like to share a status LinkedIn CEO Jeff Weiner shared today: