What Does Success Look Like? Revealed by 12 Highly Successful People

What does success look like?

Chances are, when you think about success, you have a few of the classic markers of success floating around your brain. Insert stock photo image of the boss working late into the night, or an image of an ecstatic but very relaxed luxury vacationer. You probably have some other more personal and perhaps more modern views of what success looks like kicking around in your head as well.

As work culture has rapidly evolved and the face of the typical entrepreneur or leader has broadened to include a greater number of individuals seeking freedom and control over their lives and livelihoods, many are left wondering, how do they do it?

Browse our list of highly successful people who are entrepreneurs, authors, creatives, speakers who walk the walk – they’ve brought success to their lives on their own terms and hopefully it will inspire you to redefine your own approach to designing your next phase of success!

1. Lauren Smith Brody

Author of The Fifth Trimester , Founder of The Fifth Trimester consulting

On Defining Success

Agency is how I measure my success. Simple as that.

Success is being able to chart your own course freely — either as an entrepreneur working a mishmash of hours so you can do all of the mom stuff too, or in a more traditional workplace, where you foreground challenges, ask for what you need, and improve culture for everyone around you in the process.

The Realization of Success

When I turned down Goldman Sachs. They wanted me to come lead a business development seminar for potential female clients…but wanted me to do it for free.

Believe me, I would have loved the credibility that comes with putting their logo on my website as a “client,” but there was no way I could stand in front of a room of entrepreneurial women and talk about things like the wage gap and the Motherhood Penalty and not get paid myself.

It was scary to say no in the moment, but by the next day, I realized I had turned a big corner in my business goals, both financially and morally.

From that point on, I had used this line:

“I save my reduced-fee and pro-bono work for non-profits and under-resourced community groups.”

It works!

Motivation for Success

My kids. It used to be that I wanted to do good work in the world and provide for my sons. That’s all still true, but the urgency of modeling motivation, grit, perseverance, and social justice has grown tremendously as they have gotten a bit older. They’re 7 and 10 now and I can already see that my time with them in my motherly clutches (ha!) is waning.

I want to succeed so that they can be motivated to do great, meaningful work one day, and so they’ll understand the importance of being an ally to women and anyone who doesn’t have all of the privilege and access they were born with.

2. Janice Taylor

Founder of Mazu

The Realization of Success

It’s funny, I am not sure I ever feel like I have reached the moment! The blessing and curse of being an entrepreneur is the relentless pursuit. So after years of chasing, I have decided to just love the process of daily discovery. Each day presents a new challenge to face the dragon, to celebrate the victory of being alive.

My business has had so many close calls of this is my last day and I am going to go back to my serving roots in the restaurant industry, yet just as I say that, something miraculous happens. It is a process and the success is in the process.

When Success is at Odds With Your Life

I think the hardest part of using your life to solve a large problem is knowing when it is time to disconnect. To allow flow take over.

At home, it is showing my girls that dreams are possible but, they do not come for free. You must be willing to do the work necessary on your self to clear your own filter so you can use more of your imagination to solve.

My girls now see what it takes to bring a dream alive and they intimately see that yes, even a woman can have dreams that are contrary to our current culture. As a mother, I feel an incredible sense of duty and obligation to show my girls the process of work as well as the joy of what they can become.

How Others Perceive Your Success

For me, success has nothing to do with money, houses, cash or anything exterior.

A long time ago, I grew up with nothing, my mom worked 3 jobs and I was absolutely convinced in my younger years that if I just made money, I would be happy. Well, I made money and I was still stuck with this nagging feeling of sadness.

Later on, I discovered that all of my struggles were on purpose so that I would intimately understand, feel and know the problem I was born to solve.

I believe inherently in every person is the problem/purpose that only they can solve with their imagination. I am fuelled by the deep understanding and satisfaction that I am here to solve it. It is not glamorous but is deeply fulfilling.

Motivation for Success

Death mostly. Sounds awful but really I know my time here on Earth is finite.

I spent many years in sadness, trapped in my ego from the circumstances of my life. I now understand fully I was put through all of that to be prepared.

I have witnessed so many things in my life that I truly don’t want to waste one day. I feel a sense of mortality in my life and I want to cherish every moment. So if it means truly getting over my sh*t than so be it. I was prepared to do the work so I could play the full hand of cards that I was given in this life.

The last thing I want to do is leave this Earth with a full hand of cards I was dealt without trying and trying again every day to play the full hand. Life is kind of like Poker that way but I figure that when it is my time to go, I have lived it fully, honestly and completely.

3. John Lynn

Founder of CELA – The First Ever Summit for Accelerators

The Realization of Success

When I moved on from my first successful venture, I saw that I had attached much of my self-value to the brand of the business — and not understood my own inherent talents in sales, branding, market building, and management.

After I started my next company, CELA, and achieved initial traction based on these qualities — I felt positioned to be successful long-term for the first time.

On Defining Success

Success is a system, not a condition. It is a real place that everyone needs to define regularly. Failure, too.

At CELA, the most important element of progress that we have seen present or missing in over 1,000+ founders is: defining it and redefining both on a consistent and measured basis — too often, we think of hitting KPI’s as the important act, when the critical component is committing a particular point of action to surpassing, achieving, or failing goals.

When Success is at Odds With Your Life

Our commitment to success at work is often understood categorically as success. However, the reality is that the ways we allow not-work-related activities, time, and other resources to fuel work is the true standard for durable success, happiness, and progress.

Concisely: if it seems that life is pushing hard against work priorities — you have the wrong work priorities.

How Others Perceive Your Success

This has cost me lifelong friendships, damaged family relationships, and prevented the growth of personal relationships. Not because work interfered with the time or attention paid to these people/groups/relationships, but simply because my work was not understood.

The lesson for me: it is more important for others that are important to you to understand what you do and why you do it, than it is that you do it successfully.

Motivation For Success

The emotional reward to seeing an offering, system, or experience I have built return value to a real person, with a specific problem, repeatedly — is unreal and exhilarating.

4. Gaetano DiNardi

Director of Demand Generation at Nextiva

The Realization of Success

At a macro level, a true measure of success is determined by my time to money ratio. I need to be in the upper right quadrant of the time vs money chart, at all times. If I am slipping into any other quadrant, that means I am failing somewhere.

At a micro level, I evaluate 5 factors with more granularity:

  • Time
  • Money
  • Relationships
  • Health
  • Legacy

Every month or so, I think about how I am doing in all of these “buckets” – and I apply 3 different status codes to each area:

  • Red = failing.
  • Yellow = Danger / needs significant improvement.
  • Green = Doing well.
On Defining Success and Motivation for Success

The ultimate success to me, means all of these areas within my life have a “green light” status.

Let’s look at each one:


I have to be able to do what I want in life, period. We only have limited time on earth, and I can’t spend it all working, because I’ll never get it back.

When it comes to time, the most important thing for me is having the ability to exercise my non-work related passions – things like making music, remaining healthy and spending time with friends & family.

Working remotely and living in Miami are also important factors to consider. This allows me to maximize time for things I love, as long as I am productive and getting my sh*t done too.


As the saying goes, 20s are for learnin’ and 30s are for earnin’. That couldn’t be more accurate in my case. I just turned 30 and am finally clawing my way out of debt from student loans, car payments and credit cards.

During my 20s, I was optimizing for learning and growth, but didn’t really care for cash. Being broke didn’t matter to me, because I knew that if I learned the right skills, that I’d eventually make money down the road.

Money is nothing more than a tool. Sure, you gotta survive and make enough for the minimum necessities, but why do you even a lot of money? For what, exactly?

If you’re killing yourself to make money and not enjoying your life, it’s likely time to re-evaluate your priorities.


I bucket these items into one master “relationships” category:

  • Family
  • Significant Other
  • Friends
  • Professional

You could also argue that these should be split into their own buckets, but this is how I see it.

Ultimately, you have to prioritize these somehow. Prioritize however you see fit, but choose wisely – keep in mind that you can’t completely ignore one area for too long, because it eventually backfires on you.

Mastering this bucket is very challenging, because you are dealing with many human emotions. My suggestion is to focus on the relationships that are most important to you, and then branch out as you have time.


This is a bucket I ignored for far too long, and have recently made significant changes. Why?

For one, I was getting chunky. I’ve always been in amazing shape – muscular, lean and athletic. However, it’s incredible what a few years of working in tech can do to your body. You start getting stressed, eating poorly – and BOOM, you’re 20 pounds heavier than you were in college. Not to mention you’re sitting down on your ass for most of the day.

This bucket is simple – WORK FITNESS INTO YOUR SCHEDULE. Set calendar events if you have to, but just force yourself to do it. That’s it. Get a FitBit or Apple Watch… which might help keep you on track.


Legacy is something you have to balance with your time and availability to pursue passion projects. But legacy is also what people remember you by – meaning, not what you did for them, but how you made them feel.

What will people say about you when you’re gone? This is powerful.

For me, I want to be known as a guy who made great music, was a tremendous marketer, and an all around great guy with a heart of gold. How does this happen?

  • Be likable.
  • Be a great listener.
  • Have a warm spirit.
  • Produce amazing content.
  • Make people feel good.
  • Give free advice to youngsters, pay it forward.
  • If you have a lot of money, never talk about it.
  • Support a charity or great cause, if you can.

At the end of the day, there will be occasional times when you don’t feel like you’re on the right path, but it should only be temporary.

When you start to feel like that every day, for an extended period of time, you’ve got a problem.

5. Abigail Hunter-Syed

VP of Operations at LDV Capital

The Realization of Success

At LDV Capital, we invest in deep technical people building visual technology businesses. When LDV Capital started in 2012, many people dismissed visual tech as “cute, niche and science fiction” but now, nearly everything you see in the tech and investment spheres centers around how machine learning, artificial intelligence and computer vision are disrupting legacy business.

It’s great to see the mainstream finally recognizing our belief, that visual technologies will improve businesses and the world we live in. It is even better to see the fantastic visual tech teams that we invest in create valuable businesses and improve the world we live in.

On Defining Success

Success is turning a vision into reality. While it may be an iteration of my initial idea, bringing it to life is my ultimate success.

When Success is at Odds With Your Life

You can find success in all aspects of life, there are career successes but there are so many other successes in life that. For me, these are all imperative to who I am.

Why am I successful today? I woke up and went for a run then got my toddler fed and dressed in a (somewhat) matching outfit for daycare, so I walked into work feeling confident and was able to close a new deal.

In my opinion, my life is made up of a bunch of tiny wins that feed overall success, nothing is at odds.

Motivation for Success

I am motivated by progress. I have overarching goals for my day, week, year, 5 years, etc. Checking off the boxes, adding in next steps, tracking back to my goals, helps me understand all of the work I am doing adds up to making big things happen.

6. Justin Ip

Founder, Kick Health

The Realization of Success

We get emails daily from customers telling us how life-changing it is for them to feel confident in stressful situations with Kick’s beta-blockers in hand. It’s such an amazing feeling to open your virtual doors after years of hard work and have customers truly excited about what you’re providing.

Kick offers support to individuals in their biggest moments – presentations, important meetings, public speaking events, and first dates – empowering them to own the moment versus having the moment own them. When the New York Times reached out for an interview two weeks after launch, I knew we might be onto something, and offering a useful solution to the millions of people who deal with situational anxiety daily.

This journey has shown me how false the myth of overnight success really is – it took more than a year of grinding and creating before we launched. To see such an initial positive reaction from the market makes the struggle a bit easier as we pursue our overall goal of helping people become their most confident selves.

On Defining Success

As I’ve progressed in my career, my definition of success has evolved. For me, success is a process of exploration rather than a destination.

My career has been a bit eclectic – I’ve worked in government contracting, at an experiential travel magazine, for an outdoors app startup, and now as a founder of a telemedicine healthcare company. The constant along the way has been a search of what provides authentic fulfillment for me and trying to become world-class at my craft.

The craft is dynamic and changes over time, but at any given moment, if I feel like all my previous work (and personal) experiences have somehow converged into a place where I am fully using all the skills and tools I’ve picked up along the way, I’m likely in a good spot.

Different as they may be, the experiences from the outdoor startup informs product and growth at my healthcare company. Our product and customer journeys at Kick are influenced by my learnings at the experiential travel magazine.

When Success is at Odds With Your Life

I do believe there are seasons to a life and career – sometimes work takes priority over home life, and vice-versa; but prolonged imbalances aren’t good and can lead to personal burnout and interpersonal conflicts.

Earlier in my career, I held the false belief that working harder and pushing myself to 80+ hour working weeks was the formula to get ahead and would lead to happiness.

With experience, I’ve learned to check in with myself, or perhaps a coach or therapist – someone with an external and impartial perspective, to get a sense of where I might be at any given time, and to course-correct if necessary. Her advice to me is usually – get outside and play more with people I value. It sounds quite simple, but can sometimes be surprisingly hard to practice.

How Others Perceive Your Success

We live in an increasingly psychologically-driven economy, which is one of the reasons we started Kick. What I mean by this is – a career used to be expected to just provide a stable income (and mostly for men only).

Sometime in the 1980s, Gordon Gekko made it fashionable to chase money and wealth. Millennials, despite their undeserved reputation for laziness and entitlement, have actually redefined success to be about more than just money, but also about meaning and experiences and fulfillment in both work and in life.

Not everyone agrees with this – it pains me when I hear people talk about their jobs as just a routine paycheck that enables a stable life. It’s perhaps similar to a good chef hearing that a diner is eating only for sustenance instead of appreciating how amazing a good meal can actually taste and smell and feel.

There will always be critics who don’t understand, or who are jealous of your definition of success, but it’s best to hear them out, tease out what might be useful, then continue down your own authentic path.

Motivation for Success

To perhaps paraphrase Liam Neeson in Taken, “I’ve acquired a very particular set of skills”. Skills like coding, product sense, growth, and business expertise, and I love applying these skills in a generalist sense to helping people become better, more confident versions of themselves.

I’m at a point in my career where I feel like I’ve acquired a few learnings, yet there are so many things to learn and uncover and other people to invite along. It’s a bit circular, but this journey of exploration and being able to share it with others, which makes me feel successful, which then fuels even more exploration, is what motivates me.

8. Katja Kukovic

Boating Enthusiast, Founder and CEO, Worldwide Boat

The Realization of Success

I started my boating business out of passion for sailing and the sea. It was meant to be just a side business for me, I had a full time job in marketing then.

About a year into it, one day, I got a call from two big corporations as well as a call from a major celebrity’s assistant, all wanting a yacht. That made me realize that I could turn my passion into a serious business, not just a side gig.

On Defining Success

For me, success means that we live the life we truly want, and not just the life we settle for. But it goes beyond that – success is also knowing that you are able to help others live a happier and better life.

Realizing Your Dreams

Success at work enables me to live my childhood (and adulthood) dream.

My family has a true passion for animals and a few years ago, we started a small rescue farm where we care for many abused animals, including 10 horses, 3 pigs, many chickens, turkeys, and ducks, etc.

My home office faces our horse pasture and there is nothing more rewarding than watching those once abused horses run and play happily and carefree.

9. Mike Morris

Co-Founder of Superfat

The Realization of Success

At my last company, I knew that we were going to be successful in significantly growing the company when we were able to accurately predict the result of our actions in the customer acquisition area. While this sounds pretty basic, many times it is very hard to tie specific results to specific actions with high volume customer acquisition.

Once we figured that out at Grasshopper, I knew that we had ‘cracked the code’ and would be able to grow significantly.

On Defining Success

I believe that success is being able to predict and deliver results. To me, success isn’t a goal, it’s a way of working and functioning.

When Success is at Odds With Your Life

For me, success at work makes everything easier in all aspects of life and creates an environment where I can be more productive and present at home. I don’t generally see these two things at odds.

Motivation for Success

I am motivated by large changes over time – I like to look back and compare where I am to where I was. Continuing to deliver results creates these changes.

10. Frances Simowitz

Startup Advisor, CEO & Managing Director, NUMA

The Realization of Success

It’s hard to pinpoint a moment, in the early days, it feels so much about survival that any success is quickly overlooked.

There was a month last year, where each week we subsequently closed the largest deal we had ever closed before, week over week. The moment we broke from breakeven to profitable was one where I knew we could make it and keep building.

On Defining Success

Success is different for everyone. For me, success is not a destination, it’s the path I’m on, and the freedom to build on it.

I had a previous career before this one, and I never felt like I was on the right path. Being good at my work, loving my work, and being compensated fairly for it is how I know I’m on a successful path.

When Success is at Odds With Your Life

I’ve sacrificed a lot for my success in work. It’s part of the reason I’m divorced. My husband made much more money than me, he wanted me to quit my job and have children, but I felt I couldn’t or didn’t want to be a mother until I was someone that I would want my future children to look up to.

Life is something I actively have to work on, and I’ve only this year started to intentionally prioritize things like hobbies and other interests, which can be hard for me. I’m very ambitious.

How Others Perceive Your Success

My grandparents are incredibly confused by what I do for work. I also work in startups and the compensation is not always as high as I could be making somewhere else. I had a competing offer at a large Fortune 100 company and could have been making much more money than I am now, but I chose the opportunity to be in a leadership role and continue to build my business over immediate financial reward.

This decision confused many friends and family that define success by your paycheck alone. I’ve always chosen opportunity over money every step of my career; and it’s paid off, in the end, every single time.

To me, that’s a successful trajectory.

Motivation For Success

I’d say my core competency is sales, and sales skills are necessary for leadership or as the head of any company.

My first boss in a sales role had a hypothesis that great salespeople are a bit damaged or have an innate drive to prove something. There may be a bit of that in play, but I also really care about impact.

I love seeing opportunities created, or other people learning and growing in their careers. I also feel strongly as a divorced woman, that I never want to feel like I’m reliant on a man to take care of me.

I want the freedom to build my business and my life in the way I want to, and that motivates me every day.

11. Nth Bar Fields

CEO & Co-Founder Elysian Trust, Empyrean Trust

The Realization of Success

In 2017, I decided to incorporate a nonprofit organization, Elysian Trust, dedicated to finding people with hidden talents and unnurtured mental abilities. I concomitantly co-founded its for-profit LLC, Empyrean Trust, which works to support the startups that such talented people make. And, just because I am a glutton for punishment, I co-created a generalist think-tank, Hard Problems Consulting, Pty Ltd, in Australia.

If you’re keeping score, that’s three startups on two continents in one year. Unfortunately, Hurricane Harvey hit my residence two months later, and things looked pretty dire for a time. However, our teams pulled through, and all three companies are thriving.

It was going through the challenging 2017, ironically, that cemented in my mind that we’d succeed. If you can keep three startups that are only a few months old running through a massive hurricane you’re probably going to be okay.

That is not to say I didn’t make mistakes along the way, because I did. I learned the right lessons from those mistakes and sagaciously applied them to the present.

How Others Perceive Your Success

I am an ardent believer that we can all succeed. I don’t need anyone to fail for me to rise, and no one should believe they need me to be underneath them for them to be a success.

However, to my surprise and chagrin, not everyone shares that mindset. There is a built-in hierarchy in a lot of people’s instincts. They can’t understand why I would be delighted that a company (for example) that we helped accelerate is now more prosperous than my companies all put together.

The reason is simple: the companies we help, help others. That makes the world a better place to live in for all of us.

You could say I’m more about lowering the cost of living down to as close to zero as possible for all of us than I am about getting my salary in the top percentile.

Motivation for Success

I’m not motivated to be successful. I’m motivated to make the world a better place for us all, it just so happens that the way I’ve gone about accomplishing this has resulted in success for myself and others. May it continue!

I’ve always wanted to do something with my mind to solve real problems and make valuable contributions to society. I used to think that I could make that happen through a high IQ club, like Mensa, Prometheus Society, or Olympiq Society (I’ve been a member of all of them at some point). However, those organizations don’t seem to have that kind of drive I crave. So I built what I was looking for.

In the past 12 months, my companies have helped with cancer research, combating human trafficking, cybersecurity, and several other things. I love the variety and putting my mind to good use. It makes life worth living for me.

12. Qasim Khan

Co-Founder, ZYN Drink

Realization of Success

Every business is tough. This is especially true for food & beverage, where consumers have unlimited choices for what they put into their bodies.

Our first realization that we were on the right path was when we started to see re-orders from customers in shorter-and-shorter increments of time. Also, when we started to receive inbound communications from repeat customers on how our beverages are helping them with their health & wellness.

Success in Flexible Schedules

Success in entrepreneurship means success at work and at home; they MUST go hand-in-hand.

We are working faster, harder, and longer now than ever before. My company is a labor of love for my brother and I. However, we are able to invest our time into building ZYN on our own schedules, while making sure we are involved in the lives of our families.

How Others Perceive Your Success

For many people, success is measured entirely by their financial net worth. For us, that is an important factor as well, but financial wealth isn’t all that defines success.

It is important to be multi-dimensionally successful in all aspects of life. For us, that includes family involvement, community involvement, charitable contributions, social, ethical, and environmental responsibility, sports, etc.

Taking the plunge and following the beat of your own drum can be liberating for many but there’s no blueprint for success. It used to be that success was primarily tied to making comparatively more money than others. That’s just not enough of a spectacular distinction for people today.

Knowing what will bring you success has to be fulfilling and not superficial. It has to feel like success to you, not just look like it to everyone who’s watching on social media.

Final Thoughts

There is no single definition for success. If you want to become a successful person, find what motivates you and gives you meaning.

With all the advice given by the above 12 successful people, take on whatever works for you and define success on your own terms.

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Featured photo credit: Austin Distel via unsplash.com

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