Four years ago this month, I started working for myself. It started with a small consulting project, which I thought would be a short-term gig to bridge the gap until I found my next “real” job. I had just moved to Seattle and left the job I had been at for five years, and I wanted to give myself some time to build a network in my new city and figure out what was next.
Little did I know that four years later I’d have a thriving business. I am incredibly grateful to my amazing clients and the many supporters who helped me get to this point. But it certainly was not an easy path, or a straight one.
It was terrifying to take the leap and quit my job without something else lined up. I had done it before earlier in my career, but this time felt much scarier. I was further along in my career, had hefty grad school loans to pay, and even though I was lucky to have a short-term safety net in my husband’s salary and benefits, I worried that I was making a huge mistake. I was leaving a great employer and teammates and a mission I cared deeply about for… what?
I’m not alone in this. It is becoming ever more common to have a non-linear career, and it can be paralyzing to make decisions about things that feel so high stakes. But even though I struggled with the decision, deep down I knew it was the right choice. There were many great things about my last role, but I knew it wasn’t quite the right fit for me. After a process of reflection and many fits and starts, I had realized that I really loved teaching, coaching, and helping others. While that was a part of my job, it wasn’t enough for me.
In retrospect, it seems obvious that I would end up doing what I do now, but it had never occurred to me to work as a career coach until I stumbled upon it through another consulting project I worked on. Talk about hindsight being 20/20. While the progression seems logical now, I got here the hard way – through trial and error, soul searching, and plenty of moments of “what the hell am I doing with my life?”
As an example, for a long while I was sure I wanted to work in international education. I thought it would be the perfect blend of my interest in global affairs and my experience working in the education sector, and I was eager to move away from the recruiting work I been doing since college and do something more “serious.” I went after it hard: networking, applying to jobs, and even getting very close to landing a role with a prominent international education organization. But I was the runner up, and after a serious output of time and energy I finally had to accept that no matter how hard I tried, this path just wasn’t panning out.
Would I have eventually found a job in that field? Perhaps, if I had kept at it. But instead I decided to reset. I realized that transitioning completely away from recruiting, where I had spent most of my career, probably wasn’t entirely realistic. Rather than making a jump to something brand new, I was more likely to be successful if I instead tried to pivot, using the skills and expertise I already had as a jumping off point to something else.
So I started doing some consulting work with a recruiting focus, networked liked it was my job in my new city, and soon learned about an opportunity to coach a program for recent college graduates. I decided to give it a try, and that was the experience that helped me realize career coaching was the right thing for me. It allowed me to use my recruiting experience and knowledge in a different way while coaching, teaching, and helping others – exactly what I had been wanting to do more of. As an added bonus, I could also use everything I had learned through my own career transition and exploration to help others navigate the same process.
I feel so fortunate to have found something I love to do, even though it took a while to get here. Like any job, it’s not perfect, but it certainly fits me better than any other I’ve had. And it’s funny; even though I’d never considered working as a career coach, when I was reading through some old journal entries lately I noticed one from several years before starting my business. During the midst of all my career transition angst, I had a dream that I was reviewing someone’s resume. I didn’t realize what it meant at the time, but now I see that my subconscious mind knew what I was supposed to do – it just took my conscious self a little longer to get there!
And that’s the way these things go. Despite our desire to just figure it out and get to the answer, there is never just one right answer about what to do in our careers, and those answers don’t come easily or quickly. When my clients begin working with me they are often eager to “figure out” what they are going to do as a first step, and I have to gently remind them that the figuring out process can take a while (sometimes our whole lives!).
So, where do you begin if you’re navigating this process? Let’s get to those lessons I promised in the title:
1. Create time and space to explore new options. I don’t think I would have ever ended up where I am if I hadn’t forced myself to leave my job and explore new opportunities. There was just too much inertia holding me back from doing anything really scary when I was in a full-time job. There are of course many factors to consider when deciding if leaving your job without the next one lined up is something you can do, but if you feel you are at a crossroads in your career and you are able to take some time to explore, I think it’s incredibly useful. If you’re not able to take time off from working, even a longer than usual vacation can help you get some much needed perspective and time to reflect. And there are many ways that you can explore new options without quitting your day job, from starting a “side hustle” to signing on for volunteer or board roles to taking on stretch projects at work or consulting projects outside. Whatever you do, consistently making it a priority to explore and try new things is the key.
2. Know that this process takes time. All in, it took me about five years from when I realized I wanted to do something different to landing on career coaching as that thing and actually starting to do it. It was a time of lots of learning, trial and error, and evolution, and that continues to this day. For example, I didn’t even begin offering career coaching as a service until about two years into my business, and now it’s the majority of what I do. Your timeline may be shorter than mine, but I think it helps to know that there’s not usually one “aha” moment when everything flips and you just know what it is you were meant to do. Instead, you’ll likely go through a process of learning and discovery that can feel muddy and confusing as you’re going through it, and only really becomes clear when you look back later on.
3. And that it’s never really over. In an age when the majority of jobs that will exist in 2030 don’t even exist yet, doing one thing for your whole career is going the way of the fax machine (and frankly, sounds pretty boring to me). We all need to learn the skills to successfully pivot, because chances are good we’ll be doing it again and again throughout our careers. And not only is the job market always changing, so are we! You are constantly evolving as a person and a professional, and a job that may have been a great fit for you five years ago may not be now. It’s important to regularly tune in to what you’re enjoying about your work, what you want to do more and less of, and what skills you want to continue building. This ensures you never stop learning, growing, and connecting with others, so that even when you’re not actively searching you’re leaving the door open to new opportunities. Make sure you’re setting aside time for this kind of regular reflection, even if you’re happy where you are.
Now that I’ve landed in a job I love, will I be doing this forever? Possibly, but I’d say odds are better that this work will eventually lead me to another pivot into something related but slightly different. While I have some ideas, I’m not sure what that will be. I could let that make me feel anxious about the future (and sometimes it does!), but for the most part I see it as exciting and energizing that there are a number of possible paths I could take.
In part two of this post, I’ll share some more tactical tips for career exploration and what you can do when you’re not sure what you want to do next. For now, a big thanks to everyone who has supported me during my own process of career exploration and in launching and growing my business, and cheers to a great year five ahead!