Designing a Career to Fit Your Life

A few years ago, I was working with a software developer who was “meh” about his job. He made a good living but felt apathetic about the work itself. The problem-solving aspect of his job was interesting, but something left him feeling, “eh” about it. In his words, “it was just a job,” which is okay. But based on our conversation, I could tell eventually, he would tap out because of the lack of fulfillment. So, I facilitated a little discovery with him. Turns out, the thing that brought him the most joy was deep sea fishing, but he couldn't see how that correlated with software development…and I understood that. But I kept asking him questions. I asked him to tell me all about deep-sea fishing because I, admittedly, knew nothing. At one point, I asked about what kind of tools and technology he uses, and he explained there are all sorts of tech and gadgets fishers use to track fish. Then I asked who makes that technology, and the look on his face said it all…

With my clients, I approach navigating their careers a little differently. Instead of focusing just on what skills certain companies might find valuable, I challenge those I work with to take the time to actually look at all the parts of themselves that need to be fulfilled. When we approach our careers this way, it helps us realign what we actually want to do based on who we are as whole people, not just employees. I think it’s important to acknowledge that you are more valuable than just the skills you put forward in the workplace, and in order to find fulfillment at work, bringing your whole self to your work is key.

Acknowledging the parts of us, we tuck away to find a job

What I’ve seen over the years is that people often hide parts of themselves in order to get a job. I’ve known people who have been nervous about sharing their marital status, parenthood, sense of humor, or physical appearance (gender presentation, tattoos, hairstyle, etc) when interviewing with a company because they believe those things detract from their eligibility. But, to design a career that reflects your heart, it’s important to bring your whole self to the forefront. 

Now, this may mean you get more rejections, but for anyone who doesn’t want to hire your whole self, that’s likely not the kind of company you want to work for anyway. I do want to acknowledge that it’s a privilege to be able to be picky in finding a job or career path where you can confidently bring all of who you are to the table. Not everyone is in a chapter of their life that allows for this. If you can afford to be pickier and take longer in your job search, then you can go after a more tailored opportunity, but I’m aware that some people simply have other, more pressing needs, and that’s an okay place to be too. But it’s never a bad time to think through what you want for your future self and how you can start working toward a life that reflects that.

Digging deeper with self-reflection

There are three key questions I ask people to reflect on when we first start the exploration to begin identifying what is going to be the most fulfilling path for them to take: 

  • Who are you? As a friend, sibling, or family member? As a colleague, leader, and creative? As a whole person?

  • How did you get to where you are today? Why are you at this moment right now where you’re ready for a change? What has led you to seek something different?

  • What’s next? This could be as broad as “I want to work on sustainability” or as detailed as “I want to build technical solutions for providing access to food sources in food deserts.” But think about the things you want to do and be challenged by. What problems do you want to be solving? How do you want to spend your time?

If you take the time to look at all the parts of yourself that need to be fulfilled, you can uncover what kind of roles or career paths will give you purpose, align with your priorities, and ultimately with the lifestyle you want. When you uncover what things are important to you and what makes you light up, you can begin to make steps toward integrating that into your career. I know there’s not always a clear connection between your interests or the things outside of work that bring you joy and a job that pays the bills, but if you keep asking questions and uncovering more about what you are interested in, there’s often a way to marry the two.

The client I mentioned at the beginning of this article is a great example of this. After our discovery session, his search focused on finding a job developing software that aids in deep-sea fishing. And, he found one. He was able to do something he is really good at for a company that creates tools he enjoys outside of his work life as well. This is where real “passion” for a job comes in. He didn’t necessarily “follow his passion.” He explored his skills and interests and found where they overlapped.

If you do enough digging, ask enough questions, and meet enough people, you can slowly start to uncover opportunities you never imagined would be out there, and it all starts with understanding who you are as a whole person.

Recognize the chapter you’re in

We can’t talk about designing your career without talking about your current needs a little more. It’s important to ask yourself what is going to meet the practical needs you have right now. The phase of life you’re in will dictate which of our priorities you can pay the most attention to in your search. You might be in a life chapter where you just need to meet your basic needs, pay your bills, and/or provide for others, or you may be in a chapter where you have more time to dream about the life you want to start designing. Whatever chapter you find yourself in, it’s important to honor it. You have to be honest with yourself and decide if maybe it’s okay to be “bored” in your career to be a little happier in other areas like your family life, personal life, health journey, etc.

What you need in this moment is important, so if you can afford to take longer in your job search, do it. If not, then that’s okay. There are always steps you can be making toward your ultimate goals, even in chapters that are focused more on practical needs.

How to make steps toward your ultimate goal: Start making meaningful connections

No matter what phase you find yourself in, you can set the future you want up for success by starting to make connections with people who are interesting to you. You can start by doing what I do with those I work with. I use what I call Connect Bingo, which is simply carving out time to research the kind of people and companies you’re interested in instead of just roles that sound good. This will help you identify where you ultimately belong in the workplace.

Who are the people you think are interesting? Find ways to reach out to them and nurture relationships that will help uncover more about what you really want out of a career. At the same time that this helps you discover more about what you want to work toward, it’s also creating opportunities for yourself.

I’ve said it before, but it’s worth saying again. Make connections with the intention of connecting, and don’t look at it as just a transaction. It’s a learning opportunity first that could eventually turn into a career opportunity. I know a lot of people don’t like the word networking, but if you look at it as building relationships and finding your people, you can confidently and genuinely meet people where they are, ask questions, and be curious with pure intent.

Finding belonging is more about finding people than a job

At the end of the day, finding what gives you purpose and provides that sought-after sense of belonging is really about finding your people. Your community of people where you belong will support you through job searches, career changes, new life chapters, family emergencies, etc., and provide the most stable sense of connection and belonging, beyond what a single role ever could. 

The most crucial thing as you explore all of this is, to be honest about who you are and what kind of people and opportunities really excite you. It’s okay if it doesn’t fit a perfect, corporate mold because there are roles that surprise all of us. If you can expand your view and look beyond a traditional 9-5 trajectory, staying open-minded about how to design your career, you might be surprised at the kind of jobs out there or the kind of business you could start. What I find really exciting is that the options of what we can create are truly endless when we are surrounded by the right people.

I am soon releasing a resource that can help you and those in your circle build stronger, more authentic relationships and genuine connections, and I would love for you to test it out. In collaboration with Jessie Shternshus, Owner of The Improv Effect, we have designed a conversation card deck that helps people connect on a deeper level. We have a mini version we are testing before releasing the full deck. We would love your feedback and also help in naming the deck. We’ll launch the sale of the full card deck soon, but first, help us by downloading the mini version, playing with them, and sharing your feedback with us.

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Job Searching in Uncertain Times