3 answers

When can I call myself a successful entrepreneur?

Asked Santa Ana, California

My name is Louis, and I've always felt that my path in life has never fit with the typical hours of the 9-5 cubicle career that so many others are content with. I enjoy having control and determining things for myself, rather than allowing others to dictate what, when, and how I should do things. Even with the extremely high rate of failure among entrepreneurs, my resolve to live and work how I want to remains firm. Working as hard as I need to, for as long as I need to is the nature of the job. And if it's a job I enjoy, I don't believe I'll find any issue searching for motivation to continue.

So I guess I only have one issue currently, and that's knowing when I've made it. I often hear the horror stories of people who never stop working and never allow themselves to live a full life despite their earnings. And that's not who I want to be like. The world has enough depressed workaholics. So I need to know when I can allow myself to stop grinding, for the sake of my life beyond the office.


3 answers

Alysia’s Answer

Updated Austin, Texas

Hi Louis,

My best advice is to commit to following your path to entrepreneurship and worry about the walls and ceilings later. Once you determine what you want to do, you have to pledge to yourself that you will stay aware of when you feel push-back from within. When something doesn't feel right in your gut: a decision, a commitment, a time boundary, a request, an expense, an isolation from the people you love the most, anything....promise to yourself now that you will pay attention to those signals and take time to evaluate.

The truth is that entrepreneurship is one of the toughest things to attempt, but also one of the most rewarding. However, it only remains rewarding when you nurture it and keep it in its rightful place. In other words, if it is good for you, it won't allow you to become a depressed workaholic. Trust in yourself to make the right decisions; sometimes you won't, but most of the time you will.

One other consideration: I like how Tony Robbins says "don't fall in love with your current vision." What he means is that once you achieve one dream for yourself or your business, it's not over; you must dream an even bigger dream. He talks about how some people have a dream for themselves and making their family better off; some people have a dream of making their community better off; some people have a dream to make humanity better off. Each of those are worthy causes, but each entrepreneur is different. Whatever your definition of success turns out to be today, trust me when I say that will evolve one day into something else. Go shine.

Alysia recommends the following next steps:

  • Write down on paper your own definition of success. What does it look like, feel like, smell like, taste like, sound like? Describe it in paragraph form.
  • Write 3-7 goals of things you must achieve in order to get to there from here.
  • Then write what strategies and/or action steps you need to implement by which dates to reach each of those goals within your vision.
  • Execute!

G. Mark’s Answer


A successful entrepreneur can be said to be someone who is passionate about their chosen project and whose project is self-sustaining. Note that I said self-sustaining rather than "turning a profit". There are people who are dedicated to a project and don't expect to make money, although admittedly most of us would rather make money from what we're passionate about. That being said, the first step is rather straightforward to state. Step one is to find a problem to solve. This may be a new product or a service. There is no shortage of problems to solve. The next step is to find a solution that is important enough to solve that people will be interested in it enough to allow your project to sustain itself. Once you've decided on that, you'll want to write a business plan. This involves a description of what you're planning, why it's important to do now, your target customers, the size of the market, the risks involved, a set of milestones with a timeline, and an exit strategy if any when it's appropriate to end the project. This may sound like common sense, but you would be surprised how many folks enter into projects so full of optimism that they neglect preparing for the worst or even small problems. You'll want to also describe what your management team should look like, their qualities and expertise. Putting as much detail into this plan as possible will do two major things. One, it will force you to plan and evaluate your progress. Two, it will allow you to have your plan evaluated by others, particularly anyone you'll ask for funding your project. So before you do anything at all, do the prep work -- it'll be daunting but exciting, and sure to inspire you to put the effort into it that successful projects are worth. And no matter how this step turns out, you'll gain knowledge to increase your probability of success in the future.

Kareem’s Answer


"Life Is a Journey, Not a Destination"

Ralph Waldo Emerson's quote couldn't ring truer then in the experience I've had with entrepreneurship. When I first took the plunge into entrepreneurship over 10 years ago my dream was to raise money from Union Square Ventures, the highest regarded VC in the industry. After many attempts to raise money from them, which started with many failed attempts to even get a meeting, with the right experience (three startups, one successful) and the right partners my dream came true around 4 years ago. I had achieved what I had defined for myself as "success".

But I I hadn't. I had actually just put my self in a situation where the definition of "success" just got a lot harder - I now had to build a product that users loved.

Building a product that users loved took many iterations and we finally did achieve that but again realized that our definition of "success" was just another waypoint on a road with no clear end in sight. We now had to build a business that could sustain itself. I won't spoil the ending except to say that this pattern just keeps repeating itself.

So I think the actual question you should be asking is, "How do you walk the path of an entrepreneur in the most enjoyable way possible"?

The answer to that will really depend on what's important to you.

Financial stability? Creative freedom? Singular focus? Who you work with? What you work on?

Be conscious of that and you'll be able to plot a path that works for you. If financial stability is important then you probably want to moonlight and make sure that the business you are building is self-sustainable or at least fundable before taking the plunge to full time. If singular focus and creative freedom is important perhaps you want to forgo the idea of ever building a sustainable business as an immediate goal and dedicate vacation time for short-lived projects. Your priorities and situation will be unique to you which will translate to everyone walking their own unique path. Enjoy it and you'll have "success" every step of the way.