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Having done this on my own, I have been thinking about this a lot. I think becoming a entrepreneur or even working as a freelancer is an increasingly attractive option. As I took the leap, I chronicled some of the steps I took. Here are some of my reflections (note: this may be most appropriate for business consultants, but applicable quite broadly as well)I think the most important things to do are to really assess your mindset, skills and abilities.Test your Commitment: In my career, I’ve often tested out next steps in my career by telling people what that next step might be and then judging both my reaction and theirs. For example, early in my career I would tell people “I am trying to break into consulting.” As I said it, it felt like something I really wanted to do and others acted with support. Test out “I’m making the leap to become a freelance consultant.” If it doesn’t feel right, you may want to re-think your move. You also want to challenge yourself to become comfortable with uncertainty. The question of “what if I can’t find a project” is inevitable and you will likely face this over and over as a consultant. If that lingering fear is going to overwhelm your ability to take action, this may not be the path for you.Start before you jump: Adam Grant did research showing that entrepreneurs often were risk-averse, contrary to conventional wisdom. Many people often “test the waters” before making a big dramatic jump. For me, I started doing small experiments on the side about three years before I formally took the leap. I got experience career coaching, group coaching, coaching of founders and CEO’s, consulted to small and medium organizations and developed a consistent writing practice (in 2015 I tried to write every day on Quora - this helped me improve a lot!). When getting some of this work on the side, I was transparent, pitching it as a way for me to learn and for them to get free or low-fee consulting help and people were more than excited to be part of my journey.Story, story, story: When you take the leap to freelancing, you may have a small following if you have side hustles or things you are passionate about, but you are likely not well known. This means every conversation, you need to be thinking about what your story is. This means what you are excited about, what skills you bring to the table and what you want to cause. This will help you unlock opportunities. For me, I have been telling people “I want to make the working world a better place” for years. I’m currently experimenting with the line “Working with people to be more creative and curious to do work that matters” but am continually assessing how people respond to it and tweaking it to make it more specific. The trick is to have something that is broad enough to elicit a lot of responses, but specific enough to communicate that you are really excited about one thing.Assess Your Social Capital: Start taking inventory of your network. List out who your supporters and fans are. People tend to dramatically underestimate the number of people that are rooting for them, so its good to put it down on paper - think broadly - family, friends, past colleagues, random internet penpals - anyone. If its less than 50 people, you probably are not ready yet and you’ll want to spend some time building that network before you take the leap. You can do this by first identifying things you are excited about. What energizes you? Or even better what pisses you off? This often leads you to want to solve that problem and connect with others who share the same passion.Reach out to people who’s path you want to follow: For me this meant reaching out to a number of friends and other connections that were currently freelance consultants. I had a number of great conversations and I asked them accounting, business and life questions. Some of the best advice I got is included here.Learn & test out the freelance talent marketplace: I wrote a more detailed piece on the talent marketplaces, but you should start checking out and signing up for accounts on the different platforms. You can join platforms like Catalant, TalMix, PwC and UpWork before you become a full-time freelancer. Others like a-connect, Umbrex, BTG and Genioo require you to be on your own before joining. You may also want to see if you can win a small project on one of those platforms before you take the leap just to build additional momentum. Even better if you can start lining up your own work, but these platforms are an incredible opportunity for anyone that wants to see what kind of work they can do and to start building confidence and momentum.Think about your time: One of the biggest challenges in becoming a freelancer is the lack of structure relative to being employed full-time. When you are employed full-time, much more of your schedule is fixed. As a freelancer, you have a lot more freedom. Instead of knowing exactly when you work, you will have to think about the environments that enable you to do great work, the other things you want to do during a day or week and when you can or want to work best (and on what). Your personal strategy is really how you use your time.Change your relationship with money: Full-time employment warps your mind into believing you will have a steady stream of increasing income coming in. It also tricks you into slowly increasing your cost of living as that happens - this is called the hedonic treadmill. The bad news is that freelancing means more unpredictability. The good news is that this helps you understand what really matters to you and what items actually bring your life joy. I recommend starting with a bottoms-up analysis answering the question What does a good life cost? Stephen Warley has an awesome Lifestyle Calculator worth checking out.Set a timeline: For me, I set out as a freelancer to make this a minimum one year commitment (some people even recommend 18 months). I made a number of changes in my finances, including lowering my rent and changing some of my spending habits. Mentally I committed to a full-year no matter if I actually landed any work or not. I looked at the year as a real-world grad school. If I didn’t have things to work on, I would focus on building new skills and pushing myself personally. My initial due diligence convinced me I would land some work, but in my head, my “worst case scenario” was a year off of work to learn, reflect and grow.Follow Your Excitement and Look For Opportunities Everywhere: One of the unexpected benefits I’ve experience from taking the leap to become a freelancer is that work is no longer a zero sum game. Instead of being locked-in to full-time employment, there are many more models including working remotely, working part-time and one-time teaching, speaking or facilitating gigs. I see some of my free time as an opportunity to work on fun projects, learn new skills, focus on volunteering or giving back through mentoring or as a way to reach out to others and offer my support. When I see someone doing something that inspires me, I now think about how I can reach out to them and potentially start a dialogue towards working together.I work with people who want to take the leap to be a freelancer and/or unlock more creativity and curiosity in their career. Learn more here.

I am not sure what some folks mean that happiness is our natural state. If this were so, this would presume something is preventing that natural state to emerge. I'm not sure I have observed this in real life to confirm.Why people chase happinessI think people chase happiness because they 1) do not know how to define happiness clearly and thus refer to specific aspects of happiness instead of one vague, general term and 2) these aspects tend to be desirable mental states for most to be in (on an intuitive and pragmatic, not philosophical basis, most people would choose to be happy than not). Hence, it seems worthwhile to be on the chase for that state.Characteristics of happiness statesGetting into the definition discussion can quickly get really lengthy, but for the more succinct version I will state my understanding of happiness as follows: happiness is simply a state/emotion of feeling good. This good/positive feeling comes in different flavors, each of which has very different characteristics in terms of (1) how to achieve this state (external or internal sources), (2) how it is experienced (intensity) and (3) how long the feeling lasts (duration). There are also what I call basic and advanced aspects of happiness, defined by the latter having stronger impact and duration (they are more sustainable) but in return may be weaker in intensity.When people chase happiness, they in reality chase a particular aspect of happiness. Even those who use that very general term wish for a specific way to experience happiness. What most people get confused by is that each of those aspects gets obtained in a different way, is appreciated in a different way and also varies in terms of how long one can make this feeling last. I think identifying those different aspects first, then recognizing which one it is that we each "chase" would be a good first step to understand how to "get" there. Ultimately, there is a specific way in which happiness changes and can be obtained more long-term but that is out of scope for this article.The "why" matters less than the "what"Notice I do not address the "why" people chase each aspect. I take it for human nature to desire one or more of those aspects. The philosophical, psychological or physiological reasons are beyond scope for my personal contribution to this (and also not as interesting in my opinion). What matters is for all practical reasons what exactly we seek, what the nature of the benefit looks and feels like and finally, understand what it takes to get it (and keep it as much as possible).Although I may not be completely exhaustive or mutually exclusive in the academic sense here, I would delineate the following basic aspects of happiness (each distinct, and not to be randomly mixed up into one broad, unhelpful term) would seem to be: pleasure, accomplishment, recognition, flow and altruism.Each of these differs in those characteristics I mentioned above (intensity, source, duration, etc.) but I will just give definitions here to be clear how they are distinct in my opinion.In the end, we each pursue some or all of the below through different stages in our lives, all lumped into the broad term "happiness." Instead of asking ourselves why we chase it, we should just acknowledge that as humans we just do and that we may be better off spending time understanding what it is we wish for instead of why. If anything, it can save a lot of time.That said, I do want to answer the question in short form below by answering "why do people chase (insert happiness category X)?" to the best of my understanding. Afterwards, I am defining these categories so at least it is clear what I mean by them.Why do people chase...Pleasure - to feel stimulation, for a short-term, quick gratification pay-off as an emotional "hit"Accomplishment - to satisfy their egos (more diplomatically called "drive" or "ambition")Recognition - to assert social status and to affirm their worth to the social group they care most about; to claim a legacy in some casesFlow - to get lost in the moment and be fully present with intense focus in a state without distraction and superfluous thoughtsAltruism - to feel good about helping out othersContentment - to obtain peace of mind and get off the eternal "desire machine" and feel satisfied with all the good things in their livesCalling - to get the feeling that their lives have special meaning and matter in the grand scheme of things; to assert their individualityDetachment - to be able to stop sweating the small stuff and build resilience by not taking life and setbacks too personallyEnlightenment - to achieve freedom from suffering (particularly of the demands of the ego) and experience what true bliss feels likeBasic happiness categoriesPleasureI define pleasure here as a feeling of enjoyment or excitement derived from our consumption or interaction with the things, events or relationships the world has to offer us. Note that I refer to pleasure both from more passive consumption, e.g., watching TV, eating, sleeping, etc., as well as from more active pursuits, e.g., creating art, conversing with friends, pursuit of hobbies, etc. Also, I am not restricting myself to hedonism, the typical poster-child for pleasure-seeking, but to both of what some might subjectively consider “lower” (like sensual, sensory) and “higher” (like intellectual, experiential) types of pleasure.I would estimate that for the vast majority of the time when we ordinarily use the word happiness we actually mean the mental state called pleasure. Pleasure is about stimulation, experience, and short-term gratification of our desires. But because there are many other things we also may be seeking, I continue below to be clear on the other aspects that each person values most within the "happiness family" of positive emotions.AccomplishmentAnother fundamental happiness desire is that warm, proud sense we get after accomplishing or achieving something, not unrelated to the desire for completion, for bringing to finish that which we started - small or big - and to claim it as something of our own doing. Accomplishment is about making us feel happy for having been able to do something that we or those we respect consider impressive and worth doing by overcoming notable challenges that required our application of skill, intelligence, courage, perseverance or other commonly admired virtues.RecognitionNo matter what we do or who we are, few human beings can deny the appeal of feeling recognized for something and being regarded in high esteem by our subordinates, peers, superiors, role models, in our tribes or society at large. Recognition is the happiness emotion we experience when we feel others appropriately honor what we consider our rightful standing in society.FlowFlow is a quasi-unconscious state of mind that, when we are lucky enough to fall into it, produces a sensation whereby we become unaware of the passing of time and become totally absorbed in the activity at hand. Usually, we experience powerful concentration and focus in this state, which tend to lead to greater productivity and results. Hence, when we we literally are “in the flow”, we become pure creation and activity, almost to the point of making our sense of identity and existence as a “subject that acts” irrelevant. Instead, we become action itself.While plenty of literature has discussed the concept and attempted how to replicate this mode of working, I will specifically restrict myself to analyzing the “happy feeling” sensation produced in terms of its source, intensity and duration.Note that some of you may be tempted to claim that flow is a kind of “mindfulness” and wonder why I subsequently did not create a category for this (powerful and currently very trendy) category. My short answer is that mindfulness is less an actual emotion or state of mind but a set of practices, similar to meditation, to live in the moment and in that way experience a feeling of happiness which I would categorize as a type of pleasure or contentment.Flow, on the other hand, is actually a sensation you can experience, not a practice, which is why it is included in this list. Lastly, without getting on a tangent here, one could also argue that mindfulness deals with minimization of anxiety, fear and worries, i.e., as a mechanism to reduce suffering by living in the present. Seen from that view, it also does not fit into a list of “happy feeling categories”, which we are currently focused on.AltruismWe all know the adage that giving is more rewarding than taking, or that helping others is/should be reward in and of itself. Note that I am using the term altruism here broadly to describe all positive emotion we experience after helping someone else, e.g., volunteerism, philanthropy, simple acts of kindness, nonprofit service, etc. I am aware of the philosophical debate raging for years whether “true altruism” is at all possible, but settling that is none of my concern at this point.Whether the intrinsic motivation of helping others is ultimately in our own interest or purely for another does not change the fact that for most people, having been of use to someone else tends to generally feel rewarding and good (more on nuances to that assumption below). Hence, the last major basic happiness category we need to examine here concerns how the effect of being of service to others contributes to our sense of well-being.Most of the time, people seek one or more of these basic happiness aspects.But there are also more advanced aspects I want to briefly cover as well below. Again, discussing why I group some into basic and advanced classes, and what the benefit of this is, lies currently outside the scope of this article but is something I will eventually publish separately for anyone interested in this discussion. Suffice for now to say is that the advanced categories, compared to basic ones, are harder to obtain but more worthwhile to draw from once understood. I'll leave it at that for now.Advanced happiness categoriesContentmentContentment is a happy mindset after having recognized and appreciated the good in our life (usually long after) these goods have been acquired. While the term gratitude describes a similar sensation, contentment for me is the actual result of implementing gratitude. Here’s how I think it works.Contentment is the emotion we experience when we actively learn how to appreciate what we already have in our lives, e.g., our health, our status in life, our job, our relationships, our possessions (1) as if we had just acquired them or (2) by actively evoking the most positive aspect about them that justifies their value to us.CallingAh, our calling. The big life purpose. The great meaning to it all. True passion. Few happiness categories have enjoyed such frequent and elaborate canonizing in the annals of self-help literature. And there is nothing topping this emotion on the wish list of graduates at commencement ceremonies around the world. If you ever get invited to do a commencement speech and are looking for a crowd-pleaser calling is your man. Is there anything more romantic, more hopeful, more inspirational than this notion that every person’s ticket out of the valley of darkness is the opportunity to discover a life purpose that, once identified and followed, leads to happiness and harmony with the universe ever after?As you can guess, I harbor a bit of skepticism on the degree of hype this emotion gets and the little discussed anxiety, frustration and despair it generates among those who fail to “find” it. But that’s for another article.That said, I cannot deny for sake of a complete listing here that this belief of personal meaning exists as a type of happiness sensation that, if found, can produce a good feeling about life that can last for the long term, similar to contentment.Calling is a little bit like the popular, pretty boy sibling of contentment. If contentment is Quasimodo doing his thing up in the clock tower, calling is like Richard Lionheart admired by the self-help fanbase as a knight in shining armor riding a magical steed. While contentment is about appreciation of what already is and about reducing our dependence on permanent new wants, calling is the sensation that makes us believe we are made to do what it takes to fulfill a particular purpose in life. There are countless books on the topic so I will not get into the nature of what this purpose entails or how to find it, but suffice to say that there is a fundamental assumption that there is such a thing as a true self that we wish to do justice to by following our calling. In other words, calling presupposes a large-felt want to engage in our destined work or to become the person we are meant to be. This requires introspection, reflection, experimentation and courage to move into potentially new, scary directions outside our comfort zone.DetachmentDetachment is the happy realization that you are always part of the world, yet stand above/apart from its (sometimes silly) happenings. It is the ultimate way of implementing the adage “life’s but a stage, and we are all actors on it.”Detachment is happiness from knowing how much you control your attitudes, which in return shape your thoughts and feelings to things that happen to you. To put it differently, among all the happiness strategies you consider employing, detachment protects you most from the downside. Its chief strength is not about enhancing your sensation of well-being but about protecting you from sensations of despair, frustration, anger and depression. Angry at your boss? Broken a leg? Foreclosed on your house? Lost 20% of your money in stocks? Husband divorcing you? Didn’t get into the school/job you wanted? Detachment can be your best friend in all those situations. Detachment manages your expectations by pointing out how you might more likely be engaged in “much ado about nothing” rather than facing a serious life-threatening crisis.EnlightenmentYou’ve heard about it. It’s the reason why all those Buddhist monks around the world sit and meditate for hours on end for +30 years at a time, just for a sliver of hope to attain it. It’s the Buddha’s claim to fame for having attained it. Some say perhaps at most some 10,000 people out of +6 billion humans have ever experienced it. The name of the grand prize? Enlightenment.Technically, the experience of enlightenment cannot really be put into words without sounding quite “woo-woo” or plain out wacky to ordinary people like you and me. Still, it’s real, we have cases of it, we have legions of devout people trying to go after it, and as this is an ultimate guide to happiness categories, I owe it to you to spend some time understanding the basics of this highest of emotions a human can possibly attain. So here I am, trying to put the uncommunicable into words. You’re welcome!Enlightenment is a state of mind where the boundaries of your sense of self, e.g., your ego, dissolve. What does that mean? It means that our regular perception of reality is of a subject (us) experiencing the world (the object) through the senses. But the Truth (with capital T) that the state of enlightenment teaches us is that this is not quite correct. The single hardest notion to grasp about enlightenment is that once we “reach” it, we will realize that there never was and never will be an “I” experiencing something. Put differently, when we say we are aware of the world, ourselves, etc., we are actually living an illusion. In reality, according to enlightenment, there is no person experiencing awareness, only awareness itself exists.It would take too long to describe and discuss this more here so I will stop.In summary, enlightenment is less of a happiness emotion that it is an insight about the fundamental nature of reality and how you relate to that reality. The benefits are a sense of ultimate freedom and peace, an immediate “100 points” on your exam of life. If that’s not happiness, I don’t know what is.