Gretchen Rubin

“You Can Be Direct Without Being Rude and You Can Be Assertive Without Being Disagreeable.”

“You Can Be Direct Without Being Rude and You Can Be Assertive Without Being Disagreeable.”

Interview: Alison Green.

Alison Green runs the very popular site Ask a Manager, where she answers questions from readers about office and management issue, and she also writes "Ask a Boss" on the site The Cut. She's been called "the Dear Abby of the work world."

If you want to get a quick sense of her advice, here are some of her favorite posts on various workplace issues. Fascinating!

She just published a new book called Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work. Her advice and observations are insightful, funny, grounded in real experience, and highly practical. (And what a great subtitle, right?)

I couldn’t wait to talk to Alison about happiness, habits, and productivity.

Gretchen: What’s a simple habit or activity that consistently makes you happier?

Alison: Taking time to be very deliberate about gratitude. I try to regularly reflect on the things I have to be grateful for, and it really does make me more appreciative and happier. I especially try to do it when something less-than-ideal has happened. If I make a conscious effort to think about all the ways in which things are still okay (or could be much worse), it really changes my mindset.

Gretchen: What’s something you know now about building healthy habits or happiness that you didn’t know when you were 18 years old?

Alison: It took me a while to learn that one secret to a happy life is being really honest with yourself about what makes you happy and what doesn’t. Sometimes the things that make us happy aren’t the things that we wish made us happy – whether it’s a particular romantic partner or the books we like to read or a specific career track. And other times we just don’t pay close enough attention to realize what does and doesn’t bring us joy. I’ve tried to really prioritize figuring out what brings me happiness – even if they’re things that aren’t entirely aligned with the self-image I want to have -- and then try to arrange my life accordingly. It’s worked well so far! I’m pretty happy.

Gretchen: Do you have any habits that continually get in the way of your happiness?

Alison: I’m a worst-case-scenario thinker. If something could go wrong, chances are high that I’ve thought of it and I’m worried it’s coming. At some level, I figure that by thinking through what I’d do in the event of worst-case scenarios, I’m prepared should any come around, and I’ll never be blindsided by them! But in reality, staying mired in worst-case thinking is probably too high a price to pay just to avoid the small chance that one day I’ll be blindsided by something. So it’s a bad habit, and I’d like to get out of it.

Gretchen: Which habits are most important to you? (for health, for creativity, for productivity, for leisure, etc.)

Alison: I wish my answer here was “jogging” or “knitting beanies for neighborhood children,” but the reality is that I adore doing nothing. I suppose “nothing” isn’t quite accurate – but lolling about with no responsibilities when I can just read or go down internet rabbit holes or otherwise do things that aren’t terribly productive. My work schedule tends to be too crowded on most days, and so when I get blocks of time where there’s nothing I need to be doing, I take full advantage of that. There’s something about getting to have brief periods of laziness that is incredibly refreshing and leaves me feeling much more centered and happy.

Gretchen: Have you ever managed to gain a challenging healthy habit—or to break an unhealthy habit? If so, how did you do it?

I do a lot of writing, and I used to procrastinate horribly when I didn’t feel like writing something. I finally realized that when I procrastinated on a project, I was introducing an outsized amount of negative emotions into my life – days and days of feeling the thing hanging over me and knowing that I should be doing it and feeling guilty that I hadn’t, plus knowing that I’d need to sit down and start it at some point. But if I just did whatever it was and got it out the way, I didn’t have all those days of vague dread, and I also got the relief and triumph of having it done. And truly, I think there is no better feeling than “done” for writers! So I started focusing on that feeling as a way to motivate myself to get things finished – and it’s actually completely cured me of procrastination. Similar to the way other people tell themselves they’ll have some chocolate or a beer after they finish something they’re putting off, I tell myself I’ll get to have that great feeling of having the damn thing finished – and I won’t have it hanging over me. And that’s enough to motivate me to do it.

That’s led me to a place where now I’m really disciplined about work. I have a written schedule for what I need to get done each day, and I stick to it. Doing that feels so great that it’s been very self-reinforcing, and at this point, I don’t know how I’d get things done any other way.

Gretchen: Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

Alison: I’m a Questioner through and through.

Gretchen: What made you want to write your new book?

I wrote my new book, Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Workbecause in eleven years of writing Ask a Manager, one theme that I’ve seen over and over again is that people end up less happy – both at work and in the rest of life – because they hesitate to speak up about what’s important to them. They worry that they’ll cause drama, or they’ll say the wrong thing, or that they’ll cause tension or awkwardness with people they have to see regularly. And so as a result, they stay quiet about things that often have significant impacts on their day to day quality of life, and sometimes even on their paychecks.

As a work advice columnist, I’m always trying to show people that most of the time, you actually can speak up about things that are bothering you at work – whether it’s as small as a co-worker who annoys you by playing her music too loudly or as big as a hyper-critical, micromanaging boss. And if you do, you can significantly improve your happiness level at work.

What I’ve tried to do in the new book is to walk people through exactly what those conversations can look like, to show that you can be direct without being rude and that you can be assertive without being disagreeable. It’s a book about work, but I think a willingness to jump in and have hard conversations will usually increase your happiness in all realms of life.

icon emailNewsletterLight

Get monthly newsletter updates from Gretchen.

icon schooled

Find out if you’re an Upholder, Obliger, Questioner, or a Rebel.

The Four Tendencies explain why we act and why we don’t actOur Tendency shapes every aspect of our behavior, so understanding your Tendency lets us make better decisions, meet deadlines, suffer less stress and burnout, and engage more effectively.

Take the quiz

Get My Monthly Newsletter

Sign up to get my free monthly newsletter. It highlights the best material from here, my Facebook Page, and new original work.