My Favorite Canary: When Something Is Unnecessarily Hard

Things are hard – but here are some ways to hack the hard


Elise and I have been unbelievably lucky in building Wheels Up. We have been supported by the absolute best people as we staff up and build our partner and client base. That’s not to say that things aren’t hard. In fact, sometimes they’re like, really hard. That’s to be expected when building something from scratch. As much as I never thought I’d hear myself say it, it’s all part of the journey - a part I’m learning to embrace and value.


That said, one of the canaries in the coal mine that Elise and I frequently keep an eye out for is when things are Unnecessarily Hard. You know what I mean. You’re trouble shooting one thing only to end up down a rabbit hole of cascading, intertwined issues. You’re banging your head against the wall because things are taking 10x longer than they should. You’re channeling your best Sisyphus and hating every minute of it.



Since Elise and I stumbled on this concept of Unnecessarily Hard, I’m noticing it here and there in every part of my life – and I’m on a mission to eradicate it. Here’s my 4-step process.


Step 1: Identify what kind of hard it is. One of my life hacks is understanding that there are three kinds of hard:

  • Physically hard - moving rocks all day for your backyard landscaping project when it’s 90 degrees out.

  • Mentally hard - solving complex problems like you would while writing a book.

  • Emotionally hard - making the decision to, and then following through with firing someone.

Each type of hard requires a different approach to weather and fix the problem. They each also take something different out of you once it’s over. Identifying which hard you’re facing will help you build a plan to face it.


Step 2: Acknowledge that you’re in it, and mentally prepare for how you’re going to get out of it. For me, just getting in the right mindset helps me buckle down and get through. How you navigate and recover from the different types of hard is a personal thing. I’m fairly introverted, pretty direct, and not particularly warm and fuzzy. How I handle tough situations is going to be totally different than how you might. But here’s my matrix for illustrative purposes:

Type of hard

How I get through it

How I recover

Physically Hard

Buckle down, grit my teeth, dig deep, just get it done. Sports 101.

I will be cognitively slower and generally fatigued. I plan for downtime, i.e. don’t schedule lots of meetings afterwards.

Mentally Hard

Stop, analyze, use logic and reason to figure out a solution. Be relentless.

When I crack a mentally hard task, I’m high on life - energized, fulfilled, ready to tackle anything. I leverage the high to tackle something big.

Emotionally Hard

GO SLOW. I don’t always read cues correctly from others. I respect that others may be dealing with the issue differently than I am.

These are the most exhausting problems for me to work through. I’ll need to restore my introverted self and spend time alone, reflecting. These problems are excellent opportunities for my own personal reflection and development, so I like to talk through them after the fact with a trusted confidant.

Step 3: Find your team, and tackle the thing. Figure out what you’re good at, and surround yourself with people who complement you and diversify the skillset. I like to think about it in terms of a venn diagram: what you’re good at, what you enjoy, and what only you can do. Surround yourself with teammates and colleagues that have a different venn than you do when you’re staring down the barrel of something hard.


Step 4: Get. It. Off. Your. Plate. For. Good. Once you’ve put out the immediate fire, solve that problem for good. Fix the process. Identify the root issue and resolve it. Anticipate how it’s going to crop back up and have a plan for when it does. This step is so easy to gloss over because we’re all so busy and onto the next fire drill. Put it to bed or it’s going to come back for round 2.


One of my goals for 2022 is to identify and eliminate Unnecessarily Hard things in all parts of my life, not just my Wheels Up life. This increasingly means delegating to someone whose venn diagram fits the problem better than mine does.


An example – you know what I’m not great at, I hate doing, and there are lots of people out there who can do it better than me? Mowing my lawn. So I suck it up and pay a landscaper $30 a week to do it for me. Then I don’t have to stress about having gas for my lawnmower, dodging rainy days, and not annoying my neighbors. For me, mowing my lawn falls into the Unnecessarily Hard category. Delegated. Done. I can’t tell you the relief I experienced when I finally gave myself permission to spend the money to let someone else mow my lawn. And as an added bonus, I have time to do things that I value much more than the $30 it costs me.


Elise and I are constantly watching for Unnecessarily Hard and talking about how to optimize our team and our processes to eliminate it.


Sometimes it’s a one-time issue that we just have to slog through and fix. An example of this was the difficulty we were having sizing our workloads - and invoices for that matter - accurately. We implemented a time-tracking system called Toggl to far more easily capture real hours devoted to client work, and the problem was solved. It was an arduous process setting it up and onboarding the team. But in the end, the problem was fixed.


Sometimes it’s good old fashioned load balancing, where we adjust job descriptions and to-do lists to allow everyone to focus on their highest value work, while delegating the remaining work. Our new teammate, Cara, is a perfect example of adding bandwidth in high-demand workload areas where we didn’t have enough coverage. Now everyone can focus more on what they’re the best at.


Other times, it requires self awareness, recognizing what we’re not so good at, or acknowledging that we’re trying to fix something that’s fundamentally broken. We’ve faced this with clients in the past and have had to make the tough decision to part ways when it’s just not a fit.


One of the main reasons Elise and I started Wheels Up is that we were both over the Unnecessarily Hard parts of our own corporate experiences. I don’t expect that things will ever get easy peasy, but I can tell you that a baseline agreement that Unnecessarily Hard is a real thing, and that it deserves a different approach has done wonders for getting us off the hamster wheel of recurring problem solving. Hopefully it’ll be useful for you too.