How to Define Success

This was first published on my mailing list The Looking Glass. Every week, I answer a reader’s question.

How do you define success?

Lately, I’ve been thinking a lot about what it means to be a successful professional.

Does it mean being an expert in the horizontal skills and tools required to be a good designer (or any other field for that matter)? Does it mean to be a domain expert and be able to have every information at the fingertips pertaining to that domain? Does it mean having a good work-life balance? Does it mean being a people manager? Does it mean working on a star product that users crave for? Or, a combination of all of these attributes?

As a millennial I often find myself trying to chase one of these at a time and lament over the fact that I’m not able to give my best to others. On many occasions, this leaves me with an unsettled and dissatisfying feeling.

My question to you is, how does an individual define professional success for himself/herself, and what steps can they take to keep themselves ambitious yet content and happy?

When searching for candidates that I believe will be successful designers at Facebook, I look at signals like the quality of their portfolios, their communication and problem solving skills during interviews, the strength of their references, their taste and values, and the impact they’ve had in previous roles. There are some well-trodden paths to follow if you’re looking to get hired as a designer by Facebook or other companies.

But, that’s not what you’re asking about. Your question hits a much deeper, more personal note. How can you FEEL like you are a successful professional? How can you be satisfied with who you are and what you’re doing?

Dictionaries define success as “the accomplishment of an aim or purpose”, so by definition, success depends on what your goals are, which is a personal matter. What one person deems successful could be unfulfilling for someone else. Societal and cultural norms can influence these perspectives, but only you can decide what truly matters to you.

So, how might you define, pursue, and achieve success in your career and life?

Step 1: Define success: Find your purpose.

One of the exercises I find to be the most helpful in defining success is taking time every six months or so to write down what outcomes I want to shoot for in the next year. You don’t have to share this with anyone, so be honest. Don’t let your inner critic dictate what you should want. You’re not chasing someone else’s dream — this should be entirely your own.

If you’re not sure where to start, try thinking back over the past year and taking note of when you’ve felt the most energized. What periods of time were the most satisfying for you? Not just the times you had fun, but when you’ve most embodied the person you want to be, where you’re proud of what you’re doing. Try starting sentences with “I feel successful when ____” and seeing what resonates.

Already stuck? Here are a few options to consider:

  • Making more money. Simply aiming to get rich and accumulating lots of worldly possessions could leave you feeling hollow. However, it’s completely reasonable to strive for financial independence, making enough money to comfortably afford experiences and things that give you joy, or being able to share your earnings to support the people closest in your life.
  • Learning new skills. While learning is often the prerequisite for “doing” your good taste is likely what got you into design in the first place. And it can be very gratifying to grow your skills and produce work that gets closer and closer to the quality of work from people you admire. Ira Glass has an awesome quote about this.
  • Access, influence, and control. For some, advancing in your career means you are closer to senior management, responsible for leading teams, and making decisions that impact the direction of your company. Perhaps you want to make like Aaron Burr and be in the room where it happens to help amplify your impact.
  • Recognition, awards, and fame. In design, this may be less relevant and a means rather than an end in and of itself (since design is all about the function it serves), but in many industries, like sports or entertainment, externally validated benchmarks of success are the ultimate prize. Just ask NBA superstar Kevin Durant if he’s feeling successful right now.
  • Shipping delight. Creating emotionally engaging experiences. Building something that sparks joy for millions of people around the world.
  • Social good. Impacting one of the pressing issues facing humanity, like climate change, disease, education, social injustice, or economic inequality. Being a part of something bigger than yourself to give people hope and help improve people’s lives.
  • Building strong relationships. Having friendships where you truly understand and care about each other. Being a part of a supportive community. Starting a family.

Try and be specific and measurable (S.M.A.R.T.) with your goals. And if it’s impossible to narrow it to just one aim, that’s fine. Write down two. Or more. As many as you want. But with each goal, try and stack rank them so you know when push comes to shove, where you’d make trade-offs and prioritize what matters most at the cost of other goals. This stack ranking is essential, as trying to tackle everything at the same time, or getting pulled in different directions depending on the day without a compass fixed on your true north star, is not much better than having no purpose at all.

For me, I like to backwards plan from about three to five years out and re-evaluate my purpose at least once a year. As a result, I’ve defined success in different ways at different times. In high school, success was all about good grades and college admissions. In college, success was earning a degree and landing a prestigious job. Early in my career, success was gaining skills and meeting my manager’s expectations. And now, my goal is largely to support others, make my team better, and help people across both the company and the industry have greater impact in the world.

Alongside this, I’ve also layered in personal goals: finding a true partner to marry, growing our family, and enjoying new experiences to broaden my understanding of the world.

In all cases when defining my goals, one theme has been consistent: I am excited about what I’m doing, I believe it is important, and I am excited for the possibilities in the future.

Pursuing success goes beyond seeking happiness. Anything worth doing is likely to be very hard, and is often not very fun. I find the framing of “what excites me” useful for reconciling the tension between doing something fun and doing something meaningful. There’s a palpable energy when I’m thinking about my goals and working towards my purpose, and that’s how I know I’m on the right path.

So, now that you’ve written down your purpose, make it happen.

Step 2: Pursue success: Stay focused. Play to win.

The wantrapreneur, whose goal is to start a company, but she isn’t developing prototypes, isn’t researching product-market fit, and instead she’s punching the clock at a job she finds boring, isn’t going to feel successful.

The diva designer, whose goal is to be a renowned expert, but he just rags on everything he sees without opening Sketch and showing anyone how it could be better, isn’t going to feel successful.

If you simply aren’t taking actions to make progress towards your purpose, admit it to yourself and change your ways. If you’re doing a few things right, but getting caught up in a lot of other distractions, go back to your stack-ranked priorities and shift your focus. Learn to be okay with ruthlessly prioritizing, as that is the only way to ensure you’re paying sufficient attention to your top goals.

And above all, you have to curb your bad habits. The greatest skill you can develop to achieve success is self-control. Staying focused, just like any other skill, is a muscle that can be improved with exercise.

So ask yourself — Is watching that next video, reading that next listicle, or conquering that next puzzle in Zelda on track towards your purpose? It’s certainly good to relax and recharge when you need a break, as all work and no play can easily lead to burnout. But recognize when you’re taking break, and make a plan to get back in the game as soon as you can.

How will you know if you’re on track?

It’s rare that anything in your professional career will have that Olympic Gold Medal moment where you can definitively say “I’m a winner”, but there will be some larger moments, like getting a promotion or being prominently recognized, alongside smaller moments, like making a good point in a meeting, finding an elegant design after many iterations, or hearing from people who love your product. Recognize these small victories to help stay motivated towards your greater ambitions.

Step 3: Achieve success. Or Not. But above all, keep trying.

Here’s the trick: When pursuing success, the journey is the goal.

If you’re genuinely investing your time working towards your most important personal goals, then your life will be filled with purpose. To be sure, the journey will be long and filled with challenges. But over time, with each moment of progress or failure, you’ll understand yourself better, and you can adjust your approach, or perhaps even change your goals.

Over the years, my goals have changed significantly. I worry a lot less about my manager’s expectations and a lot more about whether people on my team are thriving. I brought two small people into the world, and I’m going to do everything I can to prepare them for the future. And as I’ve had success in some areas and fallen short in others, I’ve grown more and more aware of what matters most to me.

So long as you believe what you are doing right now is important, and you’re excited for the possibilities in the future, then you should have no regrets — every decision you’ve made in the past must have been correct, as it led to where you are today. And that, in and of itself, feels pretty successful.


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