Get Comfortable With Being Uncomfortable

It's key to growth.

In our previous article on the five stages of transformation: frustration, trial and error, the “Aha!” moment, discovery and synchronization, we went over the process we all go through in order to transform and grow.

Struggling Through Frustration & Trial & Error

While we all love the part where things start to click and you feel like the painful growth period is behind you, the reality is that you’ll often-times feel like you’re just “stuck” while you’re in the first two stages: frustration and trial and error. Though an incredibly valuable emotion, the initial stage of transformation occurs when we encounter conflicting feelings about the challenge in front of us. Subsequently, as we work through the conflicting emotions that naturally occur as we become frustrated, we progress on to the next stage where we try to embrace uncharted territory. During trial and error, we frequently don’t feel fully rooted and like we have our feed under us in this new landscape.

Olga’s View: The cycle between frustration and trial and error can seem like a never-ending hell, and if you’re not careful, you may find yourself in this place for extended periods of time. If you are, indeed, finding yourself in a constant battle of frustration and trial and error, you may need to use a new perspective to overcome your circumstances.

The first step is to observe your new position and observe how everything works without you. Use these observations to accumulate ideas that fuel your trial and error and accelerate the transformation process.

Another incredible way to overcome the first two stages is to reflect upon the other three stages that you’ve gotten to as a result of a past transformation to remind yourself that feeling “stuck” is temporary. This will give you new perspective you can use to fuse together fresh ideas.

If you’d like to take things a step further, you can develop a success and failure chart to review on a regular basis. Reflect on what’s working and what isn’t, then brainstorm ways to overcome your current situation. Sometimes a daily reflection can do wonders for your career and your life.

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Katia’s View: When you’re in frustration and trial and error, it can be incredibly difficult to remember a time when you weren’t feeling this way. It’s a bit of a catch 22: for example, if you’ve always been a lawyer and have recently started taking on operations job responsibilities as well, you’ll feel frustrated that you don’t have all of the requisite knowledge and your “errors” may reinforce the feeling of frustration.

You can’t transform without skipping this part of the process, but it’s also difficult to feel confident at a time when you tend to notice your “mistakes.” You won’t complete the transformation process unless you figure out how to channel this energy into something positive. As lawyers, we tend to have type A, driven personalities that are used to succeeding. This can, actually, hinder our growth because we can get frustrated easily if success isn’t imminent.

When you’re in these first two stages, take a step back and simply acknowledge that they are hard and would be challenging for anyone. Make the frustration and trial and error less personal. Remind yourself that all of those around you who “have it all figured out,” probably went through the exact same process at some point (and may, still, be going through it). Imagine if a close friend was struggling, what would you tell them? Ultimately, it really does boil down to getting out of your own head and viewing yourself with more perspective.

Using the First 2 Stages for Continued Growth

Olga’s View: As we previously discussed, growth in life occurs through stages four and five. If you’re interested in experiencing a fulfilling life, it’s going to be up to you to learn how to take advantage of growth as much as you can.

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Stay in growth as long as you possibly can, and constantly try to spark frustration while you go through the synchronization process (this is where you merge old gems with recently-acquired gold you’ve discovered as part of your changing circumstances). This will help make each synch last longer, and it will give you an incredible boost every time you complete the process. At the end of the day, this is the stage you should cherish.

Katia’s View: The first two stages are a bit like practicing the fundamentals over and over again until they become an automatic and welcome process. There are no short cuts, you have to go through the first two stages repeatedly until the process of being frustrated and making errors becomes second nature.

We are not in a profession where we embrace making mistakes often. Most of us were drawn to law because we are natural-born problem solvers; staying in a place of discomfort where we don’t know the answer is usually pure torture for lawyers.

Yet, imagine the freedom that comes from knowing that every time you took on a new task, role, or problem – you could embrace frustration, try more, and let go of errors faster because all of these “unpleasant” processes stopped having power over you! Inevitably, you would learn how to fail, move on and learn faster, and those around you (whether at work or in your personal life), would view you as a beacon of confidence even when you’re in the middle of the “error” portion of trial and error.

Getting Comfortable with Being Uncomfortable Daily

Olga’s View: If you are constantly aware of how to make the most of your circumstances, you’ll develop the ability to conquer a diverse set of conditions. This is an invaluable skill in a world where technology and practice is constantly changing.

By getting comfortable with all of the stages of the transformation model (including the first two that can be incredibly challenging), you’ll be able to recognize where you or your department is, simplify production, and optimize your time. Trying to bring innovation to the table may feel scary, but it’s necessary to stay competent and prominent.

To succeed, you need to know where you are in the process all the time. This requires checking in with yourself on a daily basis and making sure you continue pushing yourself from frustration through synchronization.

Katia’s View: The process of transformation can be overwhelming if you look at it as one giant problem to tackle. By checking in with yourself on a daily basis – you are breaking things up into manageable chunks. You’re also engaging in an “early and often” practice that is key to success.

One of the most amazing things about being in-house counsel is that we have constant opportunity to solve completely new and unique problems. In other words, we have never ending opportunities to transform. The more we embrace the necessary part of the process — even when it’s uncomfortable and scary — the more we can use them to our advantage to grow and learn at speeds faster than we imagined!


Olga V. Mack and Katia Bloom are startup enthusiasts who embrace the current disruption to the legal profession. Long gone are the days when in-house legal departments simply manage outside counsel or provide services. Today’s legal department is a sophisticated business unit that co-manages the company’s bottom line, embraces technology, and analyzes risks constructively. Mack and Bloom love this change and are dedicated to improving and shaping the future of the legal profession. Together they passionately collect and share inspiring stories of legal leaders who are thriving through the ongoing tectonic shift. Mack and Bloom are convinced that the legal profession will emerge from this revolution even stronger, more resilient, and inclusive than before. They are currently co-authoring a manual of the skills and traits lawyers need to succeed in — and even enjoy — today’s rapidly evolving in-house legal departments. You can reach them at olga@olgamack.com and katia@katiabloom.com or @olgavmack and @bloomkatia on Twitter.