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SIX years ago, fresh out of Stanford with a degree in economics, I had what many would consider the perfect job. I was a management consultant at a prestigious firm, with an office overlooking the San Francisco Bay and a shiny new ThinkPad to boot.

My co-workers were intelligent, ambitious and fun, and I interacted with high-level executives at Fortune 500 companies. My perks included free concert tickets, ski trips and fancy dinners. I was on track to be earning six figures within three years. It was the good life I had been chasing along with my peers at Stanford.

So why wasn’t I happy?

After six months of living this supposed dream, my day-to-day life was far from satisfying. I was working 14-hour days, and most of my time seemed to be spent nudging boxes around in PowerPoint slides and agonizing over the wording of bullet-pointed items.

It felt wrong to be dreading work at such a young age. I wanted to wake up each morning excited about what was ahead. I wanted to create something of my own.

I had joined consulting with the goal of starting my own company one day, perhaps after getting my M.B.A. At the time, I believed that management consulting would best prepare me to run my own business, but I soon realized that consulting was mostly just teaching me how to be a better consultant.

Venture capital, I thought, would be a more direct path to entrepreneurship. So I quit my job as a consultant after six months and joined a venture capital firm in Silicon Valley.

I lasted just six weeks this time. Although I had indeed moved closer to the world of entrepreneurship, I found myself no closer to actually becoming an entrepreneur. To make matters worse, the work I was doing was even more painful than before, and the hours were longer.

My day now consisted of mining lists and industry reports for high-growth companies, then cold-calling their chief executives. The more C.E.O.’s I spoke to, the more “points” I got. Soon I would be judged by how many meetings I was able to schedule for my partners. And if a meeting turned into a deal, I made money. In short, I was a saleswoman.

Sales is an essential aspect of entrepreneurship, which is what initially attracted me to this job. A few weeks of selling something for which I had no passion, however, were enough for me to realize that my venture-capital gig wasn’t the good life I had imagined.

Switching jobs had not solved my problems. The truth was that I hated working in a conventional structure. I hated having a boss, working on someone else’s creation and sitting in an office all day. My time was not my own, and I was miserable. I could not bear it for even one day longer. So I quit and decided to become an entrepreneur.

Along with my boyfriend (now my husband), Parag Chordia, I raised money through family and friends and started my own technology company, a social networking site that grew to two million users. And I have never looked back — even though that company has not been profitable.

Last year, Parag and I started Khush Inc., which makes an iPhone music application called LaDiDa. It’s a kind of reverse karaoke — it creates background music when people sing lyrics into a microphone, and it is one of the top 20 paid music applications in iTunes.

As chief executive of my own start-up, I now spend my days building consumer products from the ground up, creating grass-roots marketing campaigns, pitching my ideas to investors and dreaming about the next big thing. How many people bought my product? Who saw my video? What can I do to reach more people tomorrow? These are the questions I ask myself each day.

There is a certain thrill to seeing one’s own creation in the hands and minds of thousands, sometimes even millions, of people around the world. Entrepreneurship is intoxicating.

Exciting as it may be, however, the entrepreneurial life is far from easy. Stress is a regular part of the day. Money is tight. There are frequent emotional highs and lows, and the desire to succeed can become all-consuming. Underlying all of this is the knowledge that failure is the most likely outcome.

Yet, no matter how tough things get, I wake up every morning with renewed hope and excitement for what lies ahead. The fact that I am working on my passion gives meaning to even the most mundane tasks.

My future is perhaps more uncertain than it ever has been. I may end up wealthy, or I may earn barely enough to support myself. But the realization that I face a high likelihood of failure is not enough to send me back to the corporate cubicle.

Maybe I value my time more than my net worth. Maybe my fear of boredom outweighs my fear of failure. Or, maybe I have an irrational belief that I will succeed against all odds. Whatever it is, I find the risk of entrepreneurship to be not only worthwhile but also necessary for fulfillment. Work is no longer work. It is life, and a good one.

WHAT if you’re not happy in your job? Is it possible that you’re in the wrong career entirely?

This conundrum is all too common. The pressure to “be” something starts early in life. Many children move past wanting to be professional athletes, rock stars or astronauts, but then their parents, peers and teachers begin to exert influence — maybe before young people even know where their inclinations lie.

“The way that people pick careers is incredibly primitive,” said Nicholas Lore, founder of the Rockport Institute, a career coaching firm, and author of “The Pathfinder.” It’s no wonder, then, that so many people are dissatisfied with their jobs, he said.

Consider the mother who helps persuade her son to become a lawyer, the father who urges his daughter to train to be a doctor or the student who picks a college major nearly at random because it’s time to declare one, or because it may lead to a job with a high salary.

In these cases, education may well lead to internships, first jobs and, soon, experience and decent money in careers that seem unstoppable. Except for one thing: The work doesn’t feel like a true calling.

Disillusionment can seep in quickly as a job plays out day to day. You may realize that your tasks don’t mesh well with your personality or talents. Thus, a research scientist with a vivid imagination may have to focus on one particular area for years and may conclude that there is little room for creativity, Mr. Lore said. Or a doctor may consider the work to be overly repetitive, he said, or a lawyer may see no enjoyment in arguing and dealing with paperwork.

Often, Mr. Lore said, people place too high a value on the external rewards of a job, like money, prestige and power. While these can be important, he said, a job’s intrinsic nature — the types of tasks you do, the skills these require and the perceived meaning and value of your work — are more vital to a sense of fulfillment.

Questioning your career choice is different from not being in the mood to work, finding your work difficult or not liking your boss or your co-workers. But it isn’t always easy to tell the difference between disliking a job and disliking your work environment.

“A lot of people who say that they hate what they do actually hate who they do it for,” said Barbara Safani, owner of Career Solvers, a career management firm in New York. In that case, she said, they need to work on managing their relationships rather than changing careers.

Unhappiness with your career choice goes to the root of your identity and your sense of authenticity, said Robert I. Sutton, a professor and organizational psychologist at Stanford.

People whose careers aren’t the right fit often feel like impostors, even if they are very skilled at their jobs, he said. Another symptom is constant annoyance with the demands being made of them, even though these are reasonable for the business they’re in, he said.

An additional warning sign is a feeling that their current work doesn’t rank very high in their value system, he said. For example, some people are uncomfortable with the profit motive of the corporate world and would be happier in the nonprofit sector.

“I’m not ready to say there’s a true calling, but I think there’s a better calling for many of us,” he said.

If you think a career change is in your future, he recommends saving diligently so you have some “take this job and shove it” money that allows you to make a switch.

At some point, decide whether you’re just going to put up with your current job or whether you’re committed to change, Mr. Lore said.

His firm conducts extensive testing on clients to determine their personality traits, natural talents and values. Some people are oriented toward the future and possibilities, so a career in marketing or advertising may be a good fit, he said, but a person who prefers dealing with the present and what’s right in front of her may succeed as a chef. People with highly developed spatial awareness may do best as architects or engineers, while people who are more conceptual in their thinking may gravitate toward being psychologists or economists, Mr. Lore said.

Most people assume that if they change careers, they’ll have to start at the bottom of the ladder and accept a lot less money, he said. That is sometimes true, he observed, but people can often carry pieces of their former careers along with them and gain a higher salary and position as a result.

If you do find a better career fit, don’t expect it to be a panacea. Your new job won’t always be fun-filled and satisfying. Beyond the money it provides, “I think it’s safe to say that work is overrated,” Professor Sutton said. Much of work is spent performing tedious activities that would not be at the top of your list if you had a choice, he said.

Still, people who find a “better calling” will experience fewer of those moments — and will be happier knowing that what they do is compatible with who they are.

I’M 81 and have been working since I was 13. In junior high school, I ripped old fabric off of chairs and sofas for a furniture re-upholsterer. This was during World War II, so the men had gone to war, the women were taking the men’s jobs, and kids could be hired because there was still more to do. I think I made as much money finding coins in the creases of the furniture as I got paid.

At 16, I worked unloading boxcars in a warehouse. One day, the boss asked me to run a whole department, including the inventory, the accounting and managing the people. That gave me a lot of confidence, to hear him say he believed I could do it.

My dad and I used to spend hours at the kitchen table, talking late into the night about all kinds of ideas. My mom used to call from her room for us to “Go to sleep already!” We planned to start a company together when I grew up. I loved my father dearly and nothing would have made me happier than setting up shop with him.

My dad smoked three packs of cigarettes a day; he died from lung disease in his 40s. My mom died soon after — she was a smoker, too. My biggest regret in life was that we didn’t have time to start that business. My father’s death inspired me to start a company that would help people lead healthier lives — I wanted to get on the positive side of things.

After time in the Army and different jobs, I picked up a book one day called “John Goffe’s Mill.” It was about a fellow inheriting an old flour mill and rebuilding it. By that time, my wife, Charlee, had discovered whole grains and healthy foods. The combination of her knowledge and that book inspired us to start a business — Moore’s Flour Mill — in 1972 in Redding, Calif.

I bought some millstones from a company that was going out of business in North Carolina and stored them in my garage in Redding until I was ready to start the company. My wife, two of my sons and their wives all pitched in. We learned to grind grains through those lovely stone mills and made muffin and pancake mixes.

After four years of growth and success, the small town of Redding could not support three families in such a specialized food business. Charlee and I moved to Portland, Ore., refurbished an old mill building and started up again as Bob’s Red Mill Natural Foods, with several employees. The boys bought out my share of the original operation and now supply us with granola and polenta.

It’s been more than 30 years, and I still have some of the same employees. We have more than 400 products now, sold all over the world. Our growth has been amazing. Even during the recession, people are looking for healthy foods to feed their families.

I have grown to view mistakes and bad luck differently over the years. At one point, when my sons were young, I went broke owning a gas station at a ski resort that didn’t get any snow. That was a tough five or six years. When I was 60, an arsonist burned down our mill. I was thinking of retiring after that happened, but stayed with the business to help my employees. One had just put money down on his first house. I couldn’t leave them without jobs. The company’s best years came after that.

I decided this year to give my company to my employees through an employee stock ownership plan. Anyone who has been there three years or longer will have a piece of the business. I could have sold it. We get plenty of offers. But my employees, including the sales staff all over the world, have really made it what it is today. I’ll take credit for being the energy and spirit behind it, but they deserve to own the company.

I’m 81, after all, and I can’t take it with me.

This interview with Dawn Lepore, chairwoman and chief executive of Drugstore.com, was conducted and condensed by Adam Bryant. Ms. Lepore is also a director of eBay and The New York Times Company.

Q. Do you remember the first time you were somebody’s boss?

A. I was hired at Schwab in 1983 to be the manager of the information center. The person who wanted the job was way more technical than me, and that was the reason he didn’t get the job. He was in love with the technology — I wasn’t. He was not happy about having me come in over him. And he said, O.K., you’re so smart — let’s see you do it.

Those were the days when the computers were shipped in, and they were not all put together. So you’d get these little chips, and you have to put them in the motherboard. And so he said, “Well, there’s a shipment here for you.”

So I go to the dock and there are all these boxes with computers in them. I put together 30 computers. After the guy saw me do that, at least I had a little bit of his respect, and we went on to have an O.K. relationship.

Q. What was the lesson for you?

A. Every time you take on a new role, building credibility is incredibly important. I don’t think you do it by being smarter than everybody else or knowing more necessarily than everybody else. I think you do it by rolling up your sleeves, by showing commitment, by proving that you’re willing to learn, by asking for help.

All those things earn you credibility, especially if the people who work for you feel like you’re not going to sit back and take credit for what they do, and if they get a sense that you’re going to support them, help them grow.

Q. Other key moments like that?

A. My biggest promotion was moving into the head technology role at Schwab. It’s an important job at Schwab; it reports to the C.E.O. I was 39, and it was very unusual to be a woman running technology. I remember the person who promoted me said that he had several board members call him and say: “Why did you do that? That was a really dumb decision, putting a woman in charge of technology.”

Q. Just because you were a woman?

A. There were no women C.I.O.’s back then. And I don’t have an M.B.A.; I didn’t have a computer science degree. I have a music major. It’s a very unusual profile to be in that position. The reason I got the job was that I took on really tough assignments, things nobody wanted, things that people thought were kind of impossible or thankless tasks. So I proved that I could take on things I didn’t know, and learn. I was willing to take risks, and I’ve always been a good synthesizer. And I was good at building relationships across the company.

Q. So how did the transition go?

A. The first year or 18 months were rough. I found out later that people were calling me the Ice Queen. And I was devastated. But it’s because I felt like I had to be perfect — I couldn’t show any vulnerability.

I had a boss at the time who called me and said: “You know, I really believe in you. I gave you this job, I want you in this job, I really believe in you. You have to get better, though. You have to hire a coach, you have to improve, here are the things you have to do.”

But just having him tell me, I really believe in you, I want you in this job, it made me relax. It was like, O.K., I’m not going to get fired. He’s going to give me a chance to learn on the job and so now I’m going to be a little bit more open and be willing to ask for help.

Q. What other feedback did you get?

A. So, I’m incredibly intuitive. As the technology was evolving and the business was evolving, it was very intuitive to me what we needed to do. But I was not very good about putting that into words. And so people wanted to know, where are we going? And I was absolutely convinced that it was going to be fine and we were going to figure it out.

I’m very comfortable with ambiguity. But when you’re leading a large organization, people are not as comfortable with ambiguity and they want you to be clearer about what’s happening, where you’re taking them. So I had to get better at communicating what I was thinking.