I don’t believe it’s realistic to try to be “OMG Happy” all of the time. Not every moment can be like the holidays with your family. Not every moment can be like when you snuggle under blankets with a cup of cocoa on a cold and snowy day.

Contentment, however, I think is far more achievable. It may not seem as deep-felt or as passionate, but it can be an even keel. I fear a lot of entrepreneurs especially overshoot contentment. You hold yourselves over the fire, trying to find that over-the-top giddiness and I think as a result, you often feel disappointed.

How does one find contentment? I think one way (there are millions I’m sure) is to ask yourself the following questions. They may seem simple at first…until you try to answer them.

Question One: Are you doing what you really want to do?

Carol Roth talks about this a lot in The Entrepreneur Equation. A lot of people think that they can easily turn a hobby into a job. What you discover, inevitably, is that once you HAVE to do something, it becomes substantially less fun unless you are truly passionate about it.

Have you lost the fire that was meant to fuel your business? Do you feel ensnared now?

Question Two: If you aren’t doing what you want to do, what DO you want to do?

Where is your heart taking you? When you daydream, what are you daydreaming about? How do you envision yourself when you think, “That would make me happy”?

Consider what you would want to do with all of your energy over an extended period of time. What turns you on? What makes you tick?

Question Three: Are you living life the way you want to?

Work, and the kind of work that you are doing, is of course only a small part of the equation. Are you spending enough time with family and friends? Are you doing things for yourself, not just for others? Are you investing time in things that give you joy, but may not seem “important” to you or others?

Instead, perhaps you’re feeling overworked, burnt out, or maybe you feel like you just don’t have enough fun in your life.

Have a vision for what you want life to be like and then, start aiming for it.

Question Four: If you are not living life the way you want to, what can you change?

I’m a realist. I’m not the kind of person who says, “Hey, just drop everything and go do whatever you want.” People have obligations, responsibilities, and people who depend upon them. Very seldom does that change simply because you are feeling restless or unhappy.

However, there are ways to shuffle things around so that you can get closer to the kind of life you want. If you feel that you are working too much, perhaps you can delegate responsibilities, talk to a boss, or, failing that, look for a new job with fewer responsibilities (if you can afford it).

If you feel that you are not getting enough time with your family or friends, schedule specific times. Make “meeting dates” that you aren’t allowed to miss or reschedule. Make a date with yourself once a month to do something really fun that you love doing. Little by little, take the steps that will get you to where you want to go.

Like the movie What About Bob preaches, it’s all about baby steps. Change your mindset so that you are actively molding your life into the shape you want.

Question Five: How do you define contentment?

No other question matters until you define what “content” would look like for you. Is it about financial security? Is it about the type of home you have? Is it about your family or your sense that you are achieving what you want to achieve?

Like so many things in life, feeling content is something that seldom just happens. It takes work. It takes negotiating with life. Particularly for entrepreneurs, this can seem challenging. It can seem like work should be your only priority, but is that truly the way to happiness?

Happiness is an individual decision. Define what it, and contentment, means to you.

Over to you 

What questions would you add to this list to help guide yourself to greater contentment? I’d love to hear from you!