step to success

You’re not done. It may seem like your energy is waning and your responsibilities are piling up, but midlife is a fantastic platform for success.

Don’t believe us? Look at Bryan Cranston. An astonishing actor, true – but an actor who didn’t get his first break on Malcolm in the Middle until he was 44 years old.

And he didn’t achieve widespread acclaim with Breaking Bad until he was at least 50 years old. His true artistic, financial, and cultural success came deep into his midlife years.

Why are we telling you this? Well, at Team Vippi, we have a hard time sitting back and watching people give up on the second half of their lives. Many see midlife as the end – but the clue’s literally in the name, staring at you. It’s simply another chapter in a beautiful and ever-unfolding success story.

When you reach midlife, you’re at the apex of your wisdom, experience, and energy. You can always build up more experience – but your energy will start to fade as you age. Younger folks might have more energy than midlifers and fewer responsibilities, but they don’t have many years of experience from which to learn. You’re at the intersection of your powers. 

Midlifers have a unique gift. No one should think about succeeding despite being a midlifer. You’ll succeed because you are a midlifer. We genuinely believe that this very moment in your life can fuel real and lasting success.

Let us introduce you to the five factors of midlife that can help you maintain your success. The second half of your life can be the best part.

You can become The One Who Knocks.

Rule 1: Know thyself.

Will Smith extols the virtues of hard work – and it’s carried him pretty gracefully into the second half of his life.

You’ve been through a lot. That means you’ve learned a lot, too. To hell with any life coach or guru and their “lessons” – the last few decades of your life are your guide. And all they’ve cost you is time.

What you’ve learned from your successes and failures will determine how you succeed moving forward. Use those experiences to truly know and understand yourself. Understand what you’re capable of, what your limitations are, and what you’re able to sacrifice without feeling resentful.

Imagine you’re in a canoe. Your successes are one oar, and your failures are the other. You can only propel yourself along the river by working with both. If you drop or ignore one, you’ll simply end up going round in circles.

  • Oar 1: Look back at your failures and analyze them – you’re only here today because you were able to overcome every failure you encountered. That doesn’t mean you always succeeded, but it does mean you absorbed your defeats and learned from them.
  • Oar 2: At the same time, figure out which of your qualities led to your successes – which characteristics did you demonstrate that made sure you’d triumph?

You can only know where you’re going if you know where you’ve been. The scars of your history are also your Medals of Honor. You can’t separate the two.

You are not the same person you once were. Your handling of your experiences has molded you into something altogether more powerful. It’s vital to take stock of who you are now. Having some self-awareness can help you strategize for success over the next few decades.

Realistically, you’re in a race against time. You need to be more selective about where you direct your energy. Bar-hopping every night like you did in your twenties won’t cut it.

Come to terms with your mental and physical stamina. You will have to dedicate time to improving both, preserving energy, and channeling your resources into the areas that matter. You will have to compromise more in areas of self-indulgence and streamline your life to achieve success.

Perhaps it’s cutting the booze out or waking up much earlier. Maybe you have to bail on your weekly poker night with friends to focus on work. It’s possible that, for just a little while, you have to sacrifice some family time to start seeing results.

Success always comes at a cost. But taking stock of your successes and failures can help you work out the best way to manage your time.

Success doesn’t always mean you have to be Numero Uno.

Sometimes, the sacrifice required is too great. It isn’t always essential to be number one. The difference between being number one and number two can be marginal – but the effort required to edge to the top may be significant and cost you in another area of your life.

If you were an employer, think about which of the following you’d hire:

  • A college student who graduated magna cum laude and engaged with extracurricular life
  • A college student who graduated summa cum laude and did nothing but study in their room for 4 years.

The former gives you a confident individual who can socialize and carry themselves well. The latter demonstrates extreme dedication but an unhealthy balance in their life. Who is more likely to burn out or become resentful?

The same applies to success in later life. It’s sometimes not worth gunning for the top spot. You can be a success on your terms without having to relate that success to other people. Say you’ve got a $5 million turnover, but your local rival pulls in $10 million. So what? You’ve still got a $5 million business and a family who loves you. Count your blessings.

Remember to treat time as a currency and invest it wisely. Make targeted time investments instead of placing immense pressure on your head at everyone else’s expense.

Being the best doesn’t mean the same thing as being the best version of yourself.

Rule 2: Grant yourself permission to succeed.

You might think that needing permission for your success is ridiculous. But every success comes with a set of new demands that can be too much for some folks.

Some people will mock you and distance themselves from you during a period of failure. Over many long, hard-fought victories and defeats, you’ve learned to distance yourselves from them and their jeers. You’re super-resilient to judgment now, and that’s awesome.

But what if you succeed after repeated failures? Does your plan actually allow for success? We all know what to do when we fail because it’s usually the same: Give up or try again. Failure actually makes things a lot easier. It’s why many people never try too hard – they get comfortable in that cycle.

What if you succeed? That’s when it gets complicated. Most people achieve momentary success, then head right back into failure territory – and that can really knock the wind out of you.

Remember Ice, Ice Baby by Vanilla Ice? Of course, you do; that bassline just popped right into your head. But no one remembers his next successful song – because he didn’t f*cking have one. Simple.

Success is a level with different devils. Once you reach a new height, it’ll put you up against different sets of people with different expectations, a new level of competition, and a trickier set of rules. Plus, new heights leave you further to fall. Some people are ready for that. Some aren’t.

It’s like a video game. Maybe you beat a tricky boss and get rewarded with a better weapon to take to the next level – but all of the puzzles are harder, and the enemies are bigger. There’s always another level of success to aim for, and it gets harder and harder to maintain every time you climb.

Ask yourself:

  • Can you cope with success?
  • Are you prepared for it?
  • And if the answer to the above two questions was no, is this the reason you’ve not permitted yourself to reach that level?

(Note: Vanilla Ice is now a pretty successful realtor. Guess he must’ve found a way to succeed during midlife.)

Rule 3: The people in your crew will determine how you do.

The people around you will determine your successes. No one can succeed solo, but you might end up working on your project alone, or at least with very minimal support. That doesn’t mean you can’t, in the words of renowned realtor Vanilla Ice, “stop, collaborate, and listen.”

Even Tarzan sometimes had to howl and summon the animals to his aid. The Lone Ranger succeeded because he could call on Tonto. Batman went out to defeat criminals on his own but often had to contact Alfred, his loyal butler, for gadgets and logistical support.

Even if the people around you aren’t active collaborators, you need to know they’re rock solid and happy to step up when needed.

If you’re dedicated to a project, you’ll need time to focus on it, which means time away from your family and other responsibilities. Does your partner have your back? Can they function in your absence? Have an open, honest conversation with them about your expectations – and theirs, too.

While you’re putting your energy into the source of your success, you need a partner who can step up as a “double parent” and cover for you at school functions. And they’ll have to understand how you’re striving for success, come to terms with your goals, and put all resentment to one side. Are they ready? Are you prepared to ask that of them?

And it’s not just your personal connections that play a crucial role – your network determines your net worth. Ask yourself three questions when approaching the notion of later-in-life success:

  • Do you have mentors? They can make you aware of your pitfalls and introduce you to their network.
  • Do you have good professional advisors? A good accountant, a reliable banker, and a lawyer familiar with your industry can provide you with great connections, great advice, and a practical grounding to move forward with your operation. 
  • Do you have a mental health failsafe? If you’re striving for greatness, you’re going to want to know that you have somewhere to turn when a fuse blows. An effective therapist can provide solace at difficult times. GoodTherapy can help you find one here.

Whether you have colleagues and direct collaborators or not, make sure you’ve lined up a professional, personal, and psychological support network.

Rule 4: There’s a difference between knowledge and know-how.

success from knowledge

Courses and seminars are so tempting in later life. It’s one of the most common problems midlifers have when striving for success. “Ooh, I want to learn something – I’ll just take an online course.”

It’s awesome and feels like being in school again. But knowing about something (knowledge) is not the same as knowing how to do something (know-how). Know-how comes through repeated failure, self-correction, and developing a sense of what a successful presentation and implementation of that skill genuinely feels like.

For example, you can watch a Gordon Ramsey tutorial on making a perfect bouillabaisse on YouTube. You’ll know all the steps, how long to poach the fish, and what ingredients to use. But that course could never teach you the experience of what it’s supposed to taste like – the real end goal.

If you try to obtain knowledge rather than know-how, the true purpose of your upskilling is entirely missing from your course’s teachings. Knowledge can only get you so far; know-how from doing the process is the best way to become prolific at a skill.

A successful business will consist of many interlocking skills, most of which you’ll have to learn by doing. It’s the difference between reading and understanding sheet music with no musical talent and playing piano by ear. Later-life success will come from weaving together multiple strands of know-how formed from years of lived experience.

Rule 5: The more things change, the more they stay the same.

All the networking and know-how in the world won’t hand you success overnight. You still need hard work, grit, determination, persistence, and resolve even to get close.

The only difference between gunning for success now and doing so in your earlier years is that the version of you sitting here today is wiser, sharper, and more experienced. Combine these qualities with resilience and a strong work ethic, and you’re a formidable, unstoppable force – far more so now than ever before.

Never underestimate the power of your competitor. We often lose heart when we fail – it’s only natural. But what if you were told that the person who got the success you wanted had worked an extra hour longer than you every day and toiled on the days you took off? Maybe you’ll understand the reason for your failure a little more clearly.

Nothing works if you aren’t working.

The only difference between you and your competitor could be as simple as a single action you took that they only thought about – but were too scared to try. That could be your only competitive advantage. Treat every decision and action you make as if it’s that tiebreaker.


You’ve got so many different elements working to your advantage. It’s crazy to us that more people don’t see midlife as a second wind.

Your experience, life-learned know-how, and flourishing networks can now work to your advantage if you know how to harness their power. The rest is all mentality – the sheer, bloody-minded will to succeed. 

Team Vippi is right behind you while you take your shot.

Article resources

Bryan Cranston. (n.d.). 

GoodTherapy. (n.d.).