profile

Rusty Gaillard

The Guilty Feeling of Good Decisions

Published over 1 year ago • 1 min read

Courage is not something one does or doesn’t have; it is a decision, a choice. —Linda Lael Miller


Sometimes there is no good choice.

One of my clients, we’ll call her Jane, is in that spot.

She has to ask her aunt to move out of the family house.

The aunt has been living there rent-free for years, even though she owns her own house and collects rent for it.

Jane’s family needs the money from renting or selling the family house, and

It falls to Jane to clean it up.

Jane asked the aunt to sign a very favorable lease, letting her stay there for way below market rent.

The aunt refused.

This left Jane with two bad choices: let the aunt stay as-is, or evict her.

Jane is clear on the right decision for her and her family.

But she’s avoided making the decision.

She feels guilty pushing her aunt out of the house.


Jane’s situation is unique, but the dynamic is not.

You may have faced decisions where the right choice doesn’t feel good:

- asking a team member to work over the weekend

- telling a new employee they aren’t the right fit

- missing an important meeting to deal with an urgent family matter


Here’s what I’ve observed about these situations.

If your decision benefits a third party, like your company or your family, it’s easier to make.

You can tolerate disappointing someone because you can justify the benefit.

If your decision just benefits you, it’s a different story.

Most people have a hard time prioritizing themselves.

The guilt usually wins out.

I see this frequently when my clients contemplate:

- shutting down at 6pm to invest in their well being instead of catching up at work

- not being responsive to inbound questions and messages

- blocking dedicated work time on their calendar… and honoring it

- taking a mind-clearing break in the middle of a busy day


The decision that is right and best for you — and for others — may be uncomfortable.

That doesn’t change the truth of it being the right decision.

Here’s the question.

Do you have the courage to make uncomfortable decisions that you know are in your best interest?


To your good decisions,

P.S. For my Bay Area readers, I’m organizing a casual get-together with a business school classmate in San Francisco on Thursday with our extended networks. If you’re local and didn’t get the invitation already, reply “invitation” to this email and I’ll get it to you. It would be nice to meet face to face!

Rusty Gaillard

Executive Coach, Lifelong learner, Dad, Bass player, Outdoor Enthusiast, Former Apple Worldwide Director of Finance.

Read more from Rusty Gaillard

The key to successful leadership is influence, not authority. —Ken Blanchard Charlie has an unruly client. It is a high growth company with a great product and powerful marketing. But the operations — Charlie’s area of expertise — are a mess. They hire good people but can’t keep them. The executives micro-manage decisions. And they change direction weekly. As an operations expert, Charlie sees the problem. But he spends most of his time picking up the pieces. When he does have the...

4 days ago • 1 min read

Every adversity… carries with it the seed on an equal or greater benefit. —Napoleon Hill After running a masterclass at Salesforce last week, I held revolving door 1:1 office hours. Each person had a 15 minute time slot for laser coaching. It was an opportunity focus on a specific challenge they have & develop an action plan. Think of it like having a new suit tailored to fit you perfectly. It looks great off the shelf, but the details matter. That’s what we did in the 1:1 laser coaching...

11 days ago • 2 min read

Intelligence is not only the ability to reason; it is also the ability to find relevant material in memory and to deploy attention when needed. —Daniel Kahneman Your brain is an amazing thing. Think of how a baby learns to walk. A clear goal, experimentation, failure, feedback, and adjustment. Your brain learns how to control dozens of muscles simultaneously and in close harmony… And you walk. But walking isn’t something you can figure out rationally. If you had to control each muscle...

18 days ago • 1 min read
Share this post