Navigating obstacles at work
Ways to address challenges in your career.
Years ago, when I was deciding whether or not to leave a job, an old boss of mine gave me a solid piece of advice:
When you’re unsatisfied at work, identify what kinds of obstacles exist between where you are and where you want to be.
This simple approach has stayed with me over the past 10+ years of tackling professional obstacles. It’s also been an invaluable prompt in conversations with friends and mentees as they navigate their own careers.
In my experience, there are three types of obstacles at work:
- Obstacles you can remove yourself: for example, managing feelings of isolation on a team by finding ways to build relationships and feel better understood
- Obstacles you can remove with the help of others: for example, working with your lead to identify opportunities for the type of work you want to do
- Obstacles outside of your control that cannot be removed: for example, wanting to move into a role that isn’t possible at your organization, or any number of obstructions that may exist at a business or organizational level over which you have little influence
Four steps to navigating obstacles
This is my approach when I find myself feeling frustrated or blocked in my role. By identifying the gap(s) between where you are and where you want to be, and defining the obstacles that exist between those two states, you can chart your own path forward.
1. Decide what you want
Sounds easy, right? It’s rarely that simple: you might feel stagnant, or have a vague sense that you’re not where you want to be, but have a hard time articulating exactly where you want to go. In this case, pay attention to the environments, relationships, projects, or opportunities you value most. What enables you to do your best work? This can help you clarify what you value and what you want for your career.
2. Understand your obstacles
Now that you know what you want, you need to build an understanding of what’s in your way.
Write out your obstacles: Anything that feels like it’s standing in the way or making it more challenging to get where you want to be or do the work that energizes you. Write down anything that crosses your mind, no matter how serious it feels at the time (did your favourite pen just run out of ink? Write it down. With a different pen).
Consider the obstacle environment: Addressing an obstacle requires being aware of the context around it. Although something might be an obstacle for you, does it serve some utility or provide value elsewhere? Try to understand who it matters to, where it’s coming from, or anything else that can illuminate your path forward.
Categorize your obstacles: This is really all about making an honest effort to decide if an obstacle is within your control, or something you can remove with the help of others. This sets you up to be more productive and solution-oriented instead of letting frustration build up, or even worse, becoming apathetic. This also helps avoid the trap of assuming that an obstacle can’t be removed, which could result in leaving a job that actually could be shaped into what you want.
3. Make a plan
Now that you understand what you want and the obstacles you’re currently experiencing, you can make a plan for overcoming them.
Get creative: This means recognizing that there’s not one single path or solution to get to where you want to go. In taking a creative approach to identifying and thinking through your obstacle, you can come up with new and interesting ways to achieve what you want…or maybe even to get to a place you hadn’t thought of before. There are many different techniques for doing this type of creative problem solving.
Lean on others: Don’t keep your obstacles to yourself. Talking to people you trust can give you new perspectives and ways to navigate obstacles that you didn’t consider, or that you simply don’t have the access or ability to change on your own. You might also discover shared obstacles that you can tackle with other people, and come up with more effective solutions than you would alone.
Set others up for success: If you’re successful in removing the obstacle, ask yourself: is there something I can do to help equip others with this challenge? Is it maybe even possible to entirely remove this obstacle for others?
4. Know your limits and set boundaries
Deciding to address an obstacle doesn’t always mean that you’ll be able to overcome it. It’s also not always obvious what type of obstacle you’re encountering until you really start to engage with it. At the beginning it might look like something you can address when it actually isn’t.
Addressing obstacles takes time and energy and can also represent a risk, so you should make a conscious decision about whether you’re willing to take it on. You might ask yourself:
- What’s being dropped in order to address this?
- What risk am I taking on and am I okay with it?
These questions might very reasonably lead you to deciding to leave the obstacle in place, even if it’s one you think could be overcome with enough work. This may be a signal to look for new opportunities that better support where you want to be.
If you decide to proceed, set some boundaries: give yourself a set amount of time and effort that you’re willing to spend. Addressing obstacles often means that we’re engaging directly with something that’s blocking us from something that matters, which can involve a lot of emotional work. Make sure you have a plan for how you’ll sustain yourself through that effort.
I’ve found it really helpful to follow the great advice from Emily and Amelia Nagoski on closing stress cycles.
Encountering obstacles that can’t be removed
When an obstacle is outside of your control and can’t be removed, ask yourself:
- How does this impact my career growth?
- Am I able to contribute in a way that I feel good about?
- Is this an environment in which I can continue to grow and feel good about?
- Am I able to get whatever else I need out of work?
You might find that even with an obstacle in place, you still feel good about what you’re able to do and your work environment. You might also come to the conclusion that it’s time for you to pursue new opportunities that better support what you’re trying to achieve.
Whether you have a clear obstacle in your path, or just a vague sense of dissatisfaction, it’s worth pausing to ask yourself the question that my old boss asked me: what kinds of obstacles exist between where you are and where you want to be?
This has helped me reshape situations where I might have once considered looking for a new job, to instead improving my work and satisfaction. It’s also given me insight into what’s important to me and when it’s time to pursue something new.
I hope it can be useful to you too, either as a response to obstacles you’re currently facing or as a forward-looking exercise to help you define where you want to go and how you’ll get there.
Thank you to Alaine Mackenzie, Nicole Evans, and Cassie Kaiser for providing feedback on a draft of this post.
