A simple way that most people can know when they are successful is whether they have met the predetermined metrics that they set for themselves.
It all goes back to the vision, the mission, the goals, the to-do list that you've previously set for yourself. When you have determined the direction and the destination and have some measurable quantum in there and you've reached that, that is when you can, unambiguously, without any external or internal debates, say, "I am successful." You set the parameters for that.
The danger is when people use external sources as validation for "their success." Your success is your success. That is how you measure it. You determine the metric. You determine the measurement tool. You determine the time frame. You determine the category, direction, and the field of endeavor. It's all up to you. The secret then, of course, is that it's all up to you to achieve those metrics because you've just given yourself no excuse. They weren't some third-party goals, directions, or themes thrust upon you by, many times, some ill-conceived idea from your boss or another source. Rather, they were ones that you pondered on and gave thought to. You were the one who made the plan and got to work.
That underlies this definition of success. It's not about necessarily reaching someone else's criteria for you. It's about you plotting, setting, and determining that criteria, and then going to work and getting there and being able to measure that you have done so. That is success.
Furthermore, without borrowing too much from a cliche, it's the journey that gets you there that is most satisfying--much more than actually arriving there. I believe, and my experience has been, that it is the process of "getting to success" that is the major outgrowth and benefit of being "successful."
Also, consider the areas that you measure your success in. Maybe it's a fitness goal--you want to lose some weight. Maybe it's a family metric. It could be financial, organizational growth, or some sort of business milestone. Some are more difficult than others. Broaden your definition of success. As I look at my life, particularly in my early 20s, my goals and measurements for success were very different than what they are now. Back in those days, I was going to slay dragons, kill snakes, drill for oil, and every other clich-laden metaphor that spoke to great business success. As I went along and had my family, and my children began to grow, I realized that I was paying too high of a price for that "success." I decided to reset the metrics that I used for my success. Now my score-card is, to use another cliche, a balanced score card. I look at my children. I look at my relationships with my wife and my children. I look at the value I bring to people's lives that work with me and for me. I look at the sort of people they are all becoming. Yes, I look at financial measures. Yes, I look at budgets and income statements and other measures of business success, but I measure those in the context of, and in concert with, other measures of success.
Ultimately, I am successful when my eulogy (sorry to be morbid) includes such items as: "He lifted people, he provided opportunities to people, he was able to help people do more than they thought they could, he made life better for those around him, he was a blessing in the lives of those with whom he associated." And you can analyze or state that from a personal trait perspective, financial perspective, or personal satisfaction perspective. The ultimate measure of success, for me, is how you are remembered when you are no longer there either temporarily or permanently.
In summary, think carefully what your metrics are for your success. To quote a past politician, "It all depends on what the definition of the word is, is." You define success for you. Don't let that be driven by other people. You set the metrics for that success. Some areas of success are more difficult to measure than others, but you set those parameters and measurement tools so that you can say "I am successful," unambiguously. Don't be myopic in your definition of that word success. Look for broad definitions, look for overlapping and unrelated definitions of success. From physical, to mental, to spiritual and social, to financial and economic, understand what drives you and what creates a more complete and perfect version of you, and finally define the parameters of your success accordingly. Then you will know if you are successful.
Interestingly enough, more often than not, you don't end up where you initially determined you wanted to be. The journey is the reward. What you become as you progress towards where you thought you wanted to go is the value proposition that gets generated. It's not about getting to some arbitrary spot you chose historically. Think of that spot as something organic. Think of if as having an ability to move as you change and develop and deepen yourself, so that as you change and evolve you're able to adjust your sights and where you actually want to end up.
That makes life so much more rich. That is when you know you are successful.
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