Are you stuck in Roosevelt’s gray twilight?

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

― Theodore Roosevelt

Roosevelt once spoke about the “gray twilight”: a safe middle where people neither truly win nor lose.

Most careers end up there. The résumé looks good. The salary is similar to that of some of your more successful former classmates. But underneath, you know you’re not really daring greatly.

You’re managing.

You’re editing slides at 9 pm for someone else to make the decisions.

You’re giving clients what they asked for, not what they need, because you feel it is risky or too much work.

And the danger is living in gray twilight for decades, mistaking it for progress.

Part 1. What Gray Twilight Looks Like in a Typical Career 

Gray twilight doesn’t feel like stagnation from outside. It feels respectable. Promotions come from time to time. Bonuses arrive. Your LinkedIn profile looks good. You even get recruiters reaching out from time to time to see if you want to join a smaller organization to get a bigger title.

But if you’re honest with yourself, you measure weeks and years by hours billed or salary and bonuses earned, not impact created.

You’re reliable but rarely, or never, original.

You feel uneasy about risk, so you choose projects that maintain your reputation rather than stretch you and allow you to try to create outsized value. Yes, you may fail. But what if you succeed?

This is why gray twilight is seductive: it looks like success on the outside, but inside it feels like a failure. Dostoevsky said the worst suffering is not pain, but meaninglessness.

I know this gray twilight well. When I started my business career, I was earning $500 a month, staying late to edit documents for someone else’s meeting. It looked respectable from the outside, but inside, I knew I was hiding in safe work, not growing. That realization pushed me onto a path that eventually led me into management consulting, and later into a top MBA school in Canada, banking, another major consulting firm, and ultimately to building StrategyTraining.com. I’ve lived the danger of twilight, mistaking movement (promotions, bonuses, awards, titles) for progress.

Part 2. Why Smart Professionals Stay There 

I heard a story of an elite golfer who described replaying his worst shots over and over until his body no longer flinched. That’s how he believed he grew. Most professionals do the opposite. They avoid the possibility of failure. And they certainly try to avoid reliving it.

And avoidance is addictive. Not the terrible addictions we worry about will afflict our family members, but more subtle ones:

- The addiction to external validation.

- The addiction to safe career moves.

- The addiction to being seen as competent and therefore being afraid to do anything where you may appear as a beginner (and by default as not competent).

These are harder to break because they are almost invisible to people around us. Therefore, it is up to us to identify them as problems and take action. And what makes it harder to pay attention to them is that they are socially rewarded. 

One subtle way twilight keeps professionals stuck is silence. They have good ideas and insights, but those ideas and insights never leave their laptops, or even their heads. They never publish, so they never can get feedback, contribute, and improve their thought leadership ability. I saw this countless times in consulting: the introverted person in the corner who had the right insight, but no one ever heard it. That’s why we run the Author Program (below). It forces you to put your thinking into print: your name, your ideas, your credibility.

Part 3. The Real Cost of Gray Twilight 

So what is the real cost of being in the gray twilight?

Ten years of ‘experience’ that is really just one year repeated ten times.

A gradual erosion of your competitive advantage and skill set, as braver peers start to pass you.

A continuous loss of energy as you get older.

You are succeeding on paper, but you know you’re not doing well.

Frankl found that in the camps, survival was about having purpose. Without purpose, gray twilight corrodes you until your identity itself starts to blur.

Part 4. Practical Exits from Gray Twilight 

The way out of this is not making reckless decisions, of course, but making well-thought-out, intelligent decisions and taking action.

Face discomfort directly. In cold-water training, for example, it is recommended to focus on the cold instead of wishing you were warm. You can do the same in your career. Focus your attention on discomfort, and it starts to lose some of its grip on you.

Expose attachments. Ask yourself: what am I most afraid to risk? My reputation? My image of competence? My stable role? My salary? My ability to get better roles because of my current position? These attachments also lose their grip on you once you make them visible to yourself. Basically, flash a light at them, and they lose some of their grip on you.

Micro-risks and new actions recalibrate the system. A baseball player with the “yips” can be retrained by practicing in low-stakes settings first. You can do this too. Share the unpolished idea in a client meeting where you have a long-standing relationship with the client and can afford to be less formal and perfect at times. Write an article or a chapter (you can join our co-authored project, see the noteworthy highlight above) sharing your approach, even if it feels scary and you have never published anything before. These are not reckless actions. They are recalibrations. You start taking different actions, and you will start getting different results.

Change your scorecard. Olympic athletes often talk about mastery, not medals. What if your scorecard was not titles, promotions, bonuses, or awards but mastery in your field? Or, perhaps, courage to pursue mastery?

Anchor in meaning. As many of you know, I spent many years living, working, and studying in South Africa. I even used to be a South African permanent resident. And the biggest hero in that country is, of course, Nelson Mandela. Mandela endured 27 years in prison without bitterness because, for him, from what we know, his cause was larger than his suffering. And when he came out, he didn’t seek revenge. If your work is only about the next role, gray twilight will pull you back. If it’s tied to something bigger, discomfort and even suffering can strengthen you. 

Part 5. The Arena Lens

When you face the next decision, apply these three questions:

- What is the upside if I try?

- What is the downside if I fail? Will I be able to handle it?

- What is the hidden cost if I don’t do it?

That third question often reveals things you may otherwise miss. The hidden cost of staying safe, staying in gray twilight, may be far greater than the visible cost of failing.

Final Words

Roosevelt said the credit belongs to the one in the arena, not the critic.

In a career, I don’t think the arena is only your company. I think it's also about the inner space where you confront fear, take calculated and intelligent risks, face discomfort, learn, apply, and risk falling short in order to grow and break out of your orbit.

Gray twilight feels safe. But it is a silent decline. It is a degradation. You can't stay still; you are either growing or going backward.

So this week, pick one place where you’ve been playing it safe. Consider applying the new lens. Step into the arena.

Your life will pass whether you do something with it or not. To me, the greater danger is not losing. The greater danger is never daring greatly.

P.S. Gray twilight may look respectable from the outside, but the arena is where growth happens. If you’re ready to step into the arena, start as an Insider or Legacy member at StrategyTraining.com. Build the foundation, see the lift in your compensation, and when you’re ready for deeper work with us, apply to work with Michael and me directly. And if you’re not sure where to begin, email team@firmsconsulting.com and we’ll point you to the resources that can shift your career and life trajectory.