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You are at:Home»OPINION»What Older Men Regret: Career, Finance, and Relationship Wisdom
OPINION

What Older Men Regret: Career, Finance, and Relationship Wisdom

Kevin TevBy Kevin TevJuly 29, 2025No Comments3 Mins Read
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A recent social media query from former Nairobi Governor Mike Sonko has sparked a widespread conversation among men aged 35 and above.

Sonko posed a hypothetical question: “To the men who are 35+, if you woke up and you were 25 again, what are some of the mistakes you would avoid this time?”

This invitation for reflection has led to a flood of candid advice, offering insights on everything from career choices to personal relationships.

A man Showing regret // Courtesy

Prioritising Personal Growth Over Distractions

A recurring theme in the responses centres on the importance of focusing on self-improvement and avoiding time-wasting activities. Many men expressed regret over past distractions.

One user, @essencebydaniel, advised, “First, stop wasting time on distractions that don’t build you up. Chase growth, not comfort.”

He further emphasized the importance of investing heavily in discipline — physical, mental, and financial — stating, “It compounds like nothing else.”        

Echoing this sentiment, @mqquote suggested: “If I were 25 again, I’d ditch the late-night partying, focus on building my savings, and trust my gut more—especially on big decisions.”

A man Showing regret // Courtesy

Building a Foundation: Finance and Career

Financial prudence and career strategy were prominent topics. Several respondents highlighted the importance of establishing a strong economic base early on.

“Look for money first,” urged @mboyadavid2012. Similarly, @CaptainKipkorir stated plainly, “I’ll get money first, before a wife”.

Relationships and Emotional Maturity

Beyond money and career, many men reflected on their past relationship choices and the importance of emotional intelligence.

@essencebydaniel advised against shallow relationships, urging his younger self to “wait for the ones who respect your values deeply”.

Another user, @SelfSuccessSaga, offered a blunter perspective: “Stop chasing women… Stack money, build muscle, shut the f** up. Focus first. Women come after.”

Others focused on personal boundaries and self-worth. @denis_nero25 advised: “Do not waste time proving your worth to people who never valued it in the first place. Protect your peace early, delay temporary highs, and stop chasing what looks good but drains you.”         

Group of men Showing regret // Courtesy

 

Embracing Risk and Overcoming Fear

A significant number of comments emphasized the need to overcome fear and embrace calculated risks.

@essencebydaniel’s final piece of advice was “stop fearing failure — it’s the best teacher”.

Some users regret plunging themselves into alcohol, which they say ruined their younger lives – something that they’ll never try again if their ages are reversed.

@Pikalorih: “Alcohol, folks, alcohol, alcohol, alcohol, alcohol……. Wooooo I’m not washing it…. ALCOHOL will finish you off…. It’s a silent, slow killer, and if you don’t believe me, just keep going, you’ll cry more than me.”

 

by  moses sagwe

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Kevin Tev

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