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I'm your work-from-anywhere mentor & cheerleader. I’m a former Googler turned freelance marketer and mindset coach, building my dream life, at home and abroad.


How To Measure Success When Building a Business

How do you measure success when you’re building a business? Learn how measuring success can help build a dream business around your lifestyle goals.


How To Measure Success When Building a Business

September 29, 2021

How do you measure success when you’re building a business? Learn how measuring success can help build a dream business around your lifestyle goals.

Anyone who starts their own business wants to be successful, but if you ask ten people what success means to them, you’re likely to get wildly different answers since we all measure them differently. Unless you know what success looks like to you, it will be challenging to structure your business and reach the goals you’ve set for yourself. 

What if success is jet-setting around the world and having time on the beach? A time-sensitive service business isn’t going to work if you’re constantly tethered to different time zones and your laptop. What if your idea of success is being around for all your family activities? You probably don’t want to start a business where you’re working 9 to 5 behind your computer, trying to meet deadlines. 

And if you’re a Type A corporate dropout craving more flexibility and income, you probably don’t want to be in meetings all day with high-end clients looking for someone on call 24/7. Whatever your idea of success is, you need to figure out how to shape your business around it. Only that way will you build a satisfying business that aligns with your lifestyle. 

It’s normal to feel a little stuck on this idea. If success isn’t just about income or climbing the corporate ladder, how do you measure success? Here are a few questions to help narrow down your ideas and start chasing your own version of success.

How to measure success for yourself

Am I Having Fun Yet?

I measure success by figuring out the amount of fun I have on a daily basis. It reminds me of those times my Dad would tease us as kids: “Are we having any fun yet?!” when we were complaining about a long drive or bickering with one another. The concept of “fun” also reminds me of that Ben and Jerry’s quote – “if it’s not fun, why do it?”

Measuring your success by fun doesn’t mean that everything in business should be fun. Nor should you be having fun all the time in life or business. Here’s a good rule of thumb:

  • 50% of the time, you’ll struggle or feel bored and frustrated
  • 50% of the time, you’ll be having fun

Your ratio will change depending on the season of your work cycle. For some people, onboarding new clients is a blast. For others, their version of fun is digging into their freelance work and making an impact. You’re also less likely to remember the monotony and savor those overall feelings of joy and bliss. 

Are you having any fun? 

Am I Making Enough Money?

I know some women get really uncomfortable talking about money. Me? I love money! And I’m not ashamed to say that, either.  It gives me the freedom to live the type of life I want, which I love. I love the power it gives me to hire other people and help them support themselves and their families, and I love maximizing it.

I definitely don’t feel that money is evil or that rich people are inherently flawed. It just doesn’t resonate with me. There is absolutely nothing wrong with wanting abundance for yourself and those around you. Of course, you should also care about things in life other than money and not let building wealth become the primary focus of everything you do. Naturally, you should also be a wise steward of your wealth and generously share your blessings.

But money is really important and you should set income expectations for yourself accordingly. Don’t let anyone waste your time by telling you that it’s not. 

I always think of the Kanye West lyric: “Having money’s not everything/not having it, is.” Who knew Kanye would drop a knowledge bomb on us about one way to measure success?

I’m lucky that I grew up in a reasonably privileged family. My Dad was a pharmaceutical sales manager, and my mom is a physician. They generously paid for my undergrad, and I graduated from college without any debt. 

But both of my parents grew up poor. My paternal grandpa worked in a sawmill, and my mom grew up under communism in Budapest, so I always had those experiences and struggles in the back of my mind. 

My Dad was a big believer in self-sufficiency and always told me: “Esther, go follow your bliss… just don’t come asking me for money.” 

I really took that to heart. Financial independence — and independence in general — has always been SUPER important to me. While neither of my grandmothers worked outside the home, as I said my mom is a medical doctor — and I’ve always been SO proud of that. As a woman, financial independence has long been one of my motivators, and you will never hear me saying, “I don’t care about the money!” Not caring about money devalues yourself, your goals, your business, and your ability to impact the world around you. How can you be a business owner without caring about money? Not caring is also a good way to get yourself in debt and deal with recurring money problems.

Can you relate to this? In my early 20’s, I got myself in a lot of credit card debt. I had to dig myself out of it by eating rice and beans (and beans and rice!) and wearing clothes and shoes with holes in them. I remember having to decline meeting a friend at Starbucks because I literally didn’t have $5 in my bank account.

During those lean years, when I didn’t bring my own lunch to work, I would share a (delicious and cheap!) banh mi with a coworker for lunch because I couldn’t afford to buy my own (we would sit on the steps outside the fancy showrooms where we worked in SoHo, NYC eating our $5 sandwich… so glamorous). Here’s my point: being financially insecure was terrible, and I will never go back there again. No, thank you.

I also am really passionate about saving money. Reading the book Your Money or Your Life in 2014 really started me on my entrepreneurship and financial independence journey. This book also helps its readers explore the question of, “How much money is enough?”. I’ve always been one striving for the ‘next thing’ – next job, next promotion, next box to check. This book also helped me slow down and appreciate the journey, not just check a box. I have a concept now of ‘enough.’

Does This Business Support the Type of Lifestyle I want to Live Now And in the Future? 

Many of us decide to start location-independent businesses because we’re burned out on the corporate grind, and we want to live a different type of lifestyle. But money alone isn’t a good way to measure your success – if it were, there wouldn’t be so many corporate burnouts looking for another way.

Your business should support you in designing your lifestyle the way you want. It shouldn’t merely create another job for yourself. Focus on the idea that you can arrange your work around your lifestyle, not the other way round. It means prioritizing what matters to you and still delivering great work.

Your business should also be allowed to evolve as your goals change. For instance, when I was first starting out, the agency model of swapping your time for client work (read: money) served me well. Now, however, I find myself wanting to scale without having to sell my time directly, and so more scalable products like courses have attracted my focus. 

Am I Making an Impact?

At some point, you’ll want your business to be bigger than yourself. To measure success, ask yourself, “Am I helping my clients get the results they need? Am I solving a problem?” 

I want to inspire others in their business and reimagine what’s possible for their success and how they measure it. So I ask myself, “Am I inspiring others and showing up for others as an example of what’s possible, helping to fuel their journey towards building an online business and a lifestyle that they love?”

How to measure success in life and business

Measuring success isn’t complicated, but it is multifaceted. One business owner may want to make six or seven figures, and another just $50k, but part-time. Remember that whatever your financial goals, part of your success is also measured in the flexibility and freedom you earn to pursue your dream lifestyle. That might be staying home with your kids, replacing your corporate income, having time for your hobbies, or traveling the world.

To reach success, it’s essential to get clear on what that means to you. You want to hold onto that and go after it with abandon. Along the way, never let anyone try to convince you their version of success for you is better. Keep going and be unwilling to compromise on the goals you’ve set for yourself.

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I'm Esther, your
work-from-anywhere mentor & cheerleader.

I’m a former Googler turned freelance marketer, business mentor and mindset coach, building my dream life in Southern Spain.

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