How to Take the Initiative In Life: Key Questions You Need to Ask Yourself

“Taking the initiative does not mean being pushy, angry or aggressive. It means recognizing our responsibility to make things happen.” — Stephen Covey

Let’s move beyond why taking initiative matters. Clearly, we all know taking initiative yields much more success, both from a professional and personal standpoint. So… why don’t people take initiative more often? I’m talking about being the first to take on new work, or to apologize to your significant other, or as simple as washing that dirty dish that’s been in the sink forever.


One Question to Take More Initiative

Let me introduce the logic versus character driven question. I recently finished Adam Grant’s Originals and he concluded that by reframing the question, it yields a completely different behavior. For example, his research showed that character praise is better than praising the act.

““That was a nice and helpful thing to do.” Others received character praise: “I guess you’re the kind of person who likes to help others whenever you can. Yes, you are a very nice and helpful person.” Children who received character praise were subsequently more generous.” — Adam Grant

Another example Grant cites is when teachers posted signs that said “don’t be a cheater” versus “don’t cheat.” The former resulted in less cheating because the students don’t see themselves that way. Yeah, they might have cheated but they prob have some logical rationale why they felt it was ok to do so. But, when it gets reframed to this is the type of person you are, the behavior changes.

So, how does this relate to us taking initiative? Let’s ask ourselves why don’t we take more initiative at work, at home, in your relationships. Chances are it’s because we have rationalized and have logic to justify our behavior. For example, perhaps it’s not your job at work to do that task, or that it’s below/above you. We don’t say sorry perhaps because the other person wronged first or that your error is minor compared to what they did.

Take the Initiative with FITYMI and Deep Acting


I play tennis at 7AM once a week. I was feeling quite sluggish out there lately, seemingly taking a while to fully wake-up and chasing down balls. Feeling frustrated with my lack of commitment, I started asking myself, “is this who I want to be? To be known as that guy who didn’t give it my all?” Heck no, I’m the guy who dives to get the tennis ball if I have to!

Diving deeper into what it takes to take initiative, ask yourself, are you helping or a helper? Are you leading or are you a leader? Being known as a type of person is way more powerful than being known to have a specific behavior or skill.

I combine the powerful question of, “what kind of person are you” with the old adage of, “fake it ’til you make it (FITYMI).”

Put simply, I’m a fan of FITYMI when it applies to positive behavioral and habit changes. What to be known as kind? Go ahead and pretend to be kind until you are that person. Or how about pretending to be the greater PowerPoint presenter ever? Sure, go for it! @Entreprenuer gives us guidelines on when how not FITYMI, so watch out for these: [11]

  1. When you think you’re the most important person in the room
  2. When you act like you’re better than other people
  3. When your language and verbal communication appears pompous and condescending
  4. When you think you know more than you do

One way to further craft your ideal character and truly live it is to utilize a technique known at actors as deep acting.

In deep acting, you actually become the character you wish to portray. Deep acting involves changing your inner feelings, not just your outer expressions of them. If you’re the flight attendant in the above example, you might imagine that the passenger is stressed, afraid of flying, or going through a messy divorce. You feel empathy for the passenger, and the smile comes naturally to you, creating a more genuine expression of warmth.

Deep acting turns out to be a more sustainable strategy for managing emotions than surface acting. Research shows that surface acting burns us out: Faking emotions that we don’t really feel is both stressful and exhausting. If we want to express a set of emotions, we need to actually experience them.

If not, think of your role model and be like that.” — Adam Grant [8]

That’s gold! Think of your role model and do some deep acting to really get to the character driven motivation. Mine is Captain Picard from the hit show, Star Trek: The Next Generation. When I’m in a difficult meeting or faced with a tough decision, I typically pretend to be Captain Picard and ask, what would he do? Heck, he has nothing to do with tennis but he still pops into my head when I’m playing!

But When Logic Gets In The Way

I know one of my core values is fairness. I think it’s applied best when I want to make sure I’m pulling my weight and contributing. It’s the worst when comparing myself to others and convincing myself that I’ve done enough.

So, when it comes to taking the initiative, my core value could either help or hurt. When I ask myself what kind of person I want to be, then the answer is I want to be the go-getter, the risk-taker, the one who’s not afraid to always be the bigger person. But when I ask myself if this is logically fair, I rationalize my poor behavior by convincing myself that I’ve done more than enough and others need to step up.

“Research confirms that, compared with their more passive counterparts, proactive people are better performers, contributors, and innovators.” — Harvard Business Review

Using character-driven questions help to motivate us to take initiative. But if you can’t turn off your logical brain, here are a few tips to overcome:

Think BIG picture. In focusing on specifics, it may not be fair. But if we take a step back, chances are we’ll realize our teammates or partner is doing quite a lot. And maybe it’s not in our love language, but it matters. In the big picture, it all balances out.

Balancing the Risk. If taking initiative is scary and puts yourself out there too much, then allow yourself to go extra conservative in a different way to compensate. Similar to having a diversified stock portfolio, balance your risky stock bets with stable, safe stocks. Always taking the initiative in instigating conversation? Then take it conservative in your opinions and responses.

You can’t control other people and you can’t logic them into behaving differently. It’s all too emotional. So, instead of focusing on them, focus on what you can control — yourself.


“Disadvantaged groups consistently support the status quo more than advantaged groups. Its core idea is that people are motivated to rationalize the status quo as legitimate — even if it goes directly against their interests.” — Adam Grant

Taking Initiative Isn’t About You

“Debunk the myth that originality requires extreme risk taking and persuade you that originals are actually far more ordinary than we realize.” — Adam Grant, Originals

Isn’t that such a comforting feeling? We don’t have to be like Tim Ferriss or Elon Musk, living at the razor’s edge of sanity, in order to achieve greatness. The research Adam Grant presents tells us that anyone of us “normals” can actually be an original.

“As they question traditions and challenge the status quo, they may appear bold and self-assured on the surface. But when you peel back the layers, the truth is that they, too, grapple with fear, ambivalence, and self-doubt.”

I equate it to like climbing a big mountain. I’m talking the kind of mountain where you’re tied up to other people in case someone falls through the ice and pray everyone remembers how to use their ice axe. When you’re in the lead position, you’re in charge of finding the route, surveying the ground for stability, and taking the first step on fresh ice. Everybody behind you gets the benefit of literally following in your well-trodden footsteps.


The beauty is as you’re leading (taking initiative), you know you’ve got a whole team that has your back. You fall in a crevasse and they’ll all be there to help you up. You know what that’s called? Friends and family. And you’d do anything for them.

My final thought is as you find the motivation to take initiative in all aspects of your life, consider the idea you’re doing it for the other important people in your life. For them, you’re going to find ways to improve things.

Ready To Level-Up?

If you want to have a better chance of achieving your goals, then check out my Epic Life Planning with a free downloadable tool. No catch, no gimmicks, just a step-by-step guide to help you obtain your unobtainium.


  1. Malcolm Gladwell on the Transformational Power of Reframing at SiriusDecisions Summit by Daniel Rodriguez
  2. Taken for Granted: Malcolm Gladwell Questions Everything (Transcript)
  3. Lessons from Leaders: Outliers by Antoinetta McKay, MPA
  4. Malcolm Gladwell: There are no shortcuts to success — here’s what will up your chances by Abigail Johnson Hess
  5. The Concept of Personal Initiative: An Overview of Validity Studies by Doris Fay and Michael Frese
  6. Managing the Perks and Pitfalls of Proactive People by Lotte Glaser and Eva de Mol
  7. When to Take Initiative at Work, and When Not To by Sharon K. Parker and Ying (Lena) Wang
  8. Originals: How Non-Conformists Move the World — Adam Grant — Book Summary by Sebastian Trzcinski-Clément
  9. Why Using Logic Alone to Persuade Others Will Fail Most of the TimeWhat research tells us about logic and emotions when it comes to the art and science of persuading others. by James Sudakow
  10. How to Keep Working When You’re Just Not Feeling It by Ayelet Fishbach
  11. 4 Ways ‘Fake It Till You Make It’ Can Backfire by Lauren Hirsch-Williams

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