A question worth asking throughout our entire business career

Your Advice To You Can Be Interesting

I’ve been asked this question countless times over the past 20 years:

“What advice would you give your 25 year old self?”

As a frequent guest on leadership podcasts and one who has been interviewed in the trade press more times than I can recall, I can tell you that the question is a common one. Why?

It’s a great question – fun for the interviewer to ask; thought-provoking for the interviewee to consider; titillating to the audience as they anticipate the response.

When I get this question, most often I point to the long hours that I put in to make a name for myself in a very crowded field. I discuss the pressure that I put on myself when I first got started as a consultant and coach. In fact, it’s common for me to describe my very first year in business – one where I billed 263 days out of the approximately 280 work days available. Sometimes, I even go deeper than that, offering stories about waking up in hotel rooms not knowing what city I was in because sometimes I would be in three cities in a week. Fun is!

Regardless, all of this discussion in these interviews is an attempt to create a palpable build-up to the answer that I inevitably offer – one I believe would be valuable to my 25 year old self, which is:

“It’s OK to give yourself a break…”

Of course, I’m not entirely sure that my 25 year old self would have taken the advice.

After all, I am a firm believer that the vast majority of successful business professionals (as measured strictly by title, responsibility, earnings, professional recognition, etc.) are willing to do the work that less successful business professionals are not willing to do. I was, and still am, willing to go the extra yard to be as exceptional as I possibly can be at what I do.

Hence, any advice that suggested that I “let up” on the accelerator probably would not have resonated in my 25 year old mind.

Nonetheless, with any luck, we mature with age!

Fast Forward To Today

As I contemplate that question about advice in light of where I am today, I must admit that it would have been the “right” advice to get (and to take) at that earlier age. It would have taught me about self-care decades before I learned the importance of it. It would have enabled me to practice patience with myself, something that I’m still trying to master to this day. Indeed, it may have provided me with the opportunity to be a little less judgmental than I was back then, especially when I saw many of my peers in constant search for the “Easy Button.”

To close, I think it’s good practice to periodically ask ourselves: “What advice would I give my 25 year old self?” 

As mentioned, it’s a great question for a variety of reasons. Perhaps, one of the best reasons that it is such a good question is that it can inspire the self-reflection that we all need to be our best selves today.

Give it a try and, if you like, let me know what you discover.


For help in developing your next generation of top leaders, please be sure to reach-out.


BTW – These ideas are based on those presented in my latest book:

INDISPENSABLE: How to Build and Lead a Company Customers Can’t Live Without (2021).

Order Your Copy Today!