The greatest obstacles to early retirement - and how to overcome them

Why are so few people actually retiring early? I think the answer lies in our fear of the judgement of others. We are judging our own actions by what others might think about us. Cultural stigma becomes internalized and we fear the judgements of others. Workless people become stigmatized. Associations with a certain character-type arise and they are judged as less valuable.  Even though this is only true for a minority of people, many people carry these false beliefs. And in unnecessarily keeping to our jobs or compensating with increasing our consumption we reinforce those believes.

Think back about a time when you had much less money available for spending or consuming literally unnecessary products and services. Some of you might have to think as far back as early childhood, when everything you could afford to buy each week was a bag of mixed sweets for example. Or you might think back of the time when you were studying. And others might just be working to make ends meet anyways. But when you imagine yourself being again in the situation where you earn or get only what you really needed and it was socially accepted. No one would say a child is poor because it only gets what it needs through his parents. Children are perfectly capable of being happy without ever considering their financial situation. Similarly it is socially accepted to be a student, who barely gets by, lives in a shared apartment and eats mostly pasta or rice.

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The picture changes when we are earning an income which allows us to buy more than we need. In todays world it is oftentimes difficult to find a job which offers just the amount of work and salary that would be needed to cover ones needs. Therefore most people are stuck working in a full time job earning more than what they needed at others times when they had less money at their disposal. So if you are mostly unconscious about your financial goals, than it is likely that you will be influenced by culture and advertisements. Ultimately this leads to a slow but noticeable increase in spending, called lifestyle inflation. You end up buying bigger apartments, bigger cars, bigger TVs, more exotic vacations, gourmet foods,…
And in doing so most people do not notice that they are not any more happy than at times when they had less money to spend. On the contrary, anxiety about losing the job or the money and depressive moods become more frequent.
Therefore the greatest obstacle to early retirement does not lie in our own capabilities or in the financial market. It is purely driven by unconscious decisions that are influenced and reinforced by the actions of other people around us. Stepping out of this cycle of lifestyle inflation requires conscious thought and action against what is cultural and social norm.

This one mental thought (how you think others will think of you) might actually be the reason you have a hard time quitting your job when you could from a financial point of view. Spending the money you earn will become more appealing, because it justifies your decision to stay at work for longer. But I argue that one should not fall into that trap and actually quit full-time work.

You can only become a well-rounded and mentally developed human being by quitting the dependency on work to hold up your image of self-worth. Giving meaning to your life outside of work and being fully confident in doing so will develop your personality in ways conventional employment never can. Employment keeps you comfortably enslaved and acts as an easy escape from confronting necessary personal and spiritual growth. Being told by others what to do with you most precious resource (your life-time) will hold you back from searching and discovering your own purpose. Realizing your highest personal potential is possible with the free time after quitting full time work. When financial independence is realized one can actually pursue personal development or enlightenment to a degree necessary to reach high states of consciousness.  This is possible because the security needed to pursue such a non-financial goal is already achieved.

Coming back to the reasons why this path is so uncommon and hard to step on in the beginning, let us dive into the aspects of personal connections. Spending years and most of your active waking hours in a social construct called companies, held together by projects, salaries and social connections, it is hard to imagine a better alternative. From personal experience I can say that this situation is likely to lead to a neglected social life outside of work. Even though people are socializing(mostly on the weekends) outside of work, social connections do not develop to the level as they would when human beings spend a lot of time together working on the same projects, having the same goals and ideals. The profound difference to the work environment here is, to choose those people yourself, according to your personal preferences and character. If you are able to develop deep and meaningful friendships with the people at work, you can call yourself lucky and is likely to be an exception rather than the rule.

But many people stay at their jobs because they have largely lost or never had such meaningful relationships to other people. And staying connected to anyone through the means of a job is better than being totally isolated. Because we do not have much to fall back on when we are outside of work, we cannot see a better alternative to work. 
To prepare for quitting your job, it is good advice to start building a reliable community of people, which you value, like to be with for extended periods, can trust and ask for advice.  To make this possible, a shared goal, which serves as a basis for common actions, is highly helpful.
(As a side note: That is exactly the reason, why I think that freely chosen living-communities can be a good place to look for such kind of human connection. They are becoming increasingly popular in alternative circles. Their intend is to replace the big circle of families of the past, where at least three generations where living together in one place, sharing their work and common goals.)

Next obstacle to early retirement and a work free life is that we lack sufficient social structures outside of work. Or to be more precise, deliberate social structures need to be consciously established to replace work related relationships. 

My advice is to prepare oneself with the following points leading up to the planned retirement date:

  1. If you are not sure that you will have enough social relationships after quitting work, start to look into alternative ways of living. WWOOFing or volunteering in communities or shared living projects can be a great way to look into such lifestyles without additional cost. You can already plan this during your regular holidays. If you are open minded to meet people who are living an alternative lifestyle and are prepared to have your beliefs challenged this can be a great opportunity to test a life not centered around consumption and the distraction of the city.
  2. Have a clear idea about the sum of money you need and calculate the date of retirement based on current income and savings rate. Stick to this goal and do not come up with excuses why you might need additional money in retirement, or any just in case ideas. It is more likely that you will end up earning money after retirement. You might find it interesting after a while to look into several part time jobs and earn money on the side. And earning a small sum of money per year is ultimately more efficient than building up the capital to earn that extra income. This is different from building up the foundation of financial independence through savings. Only with that safety are you really free to choose your own time.
  3. Avoid lifestyle inflation. Really evaluate every purchase. Will it increase your long-term happiness or is just a short term fix. Try to put every item on a wish-list for 30 days before buying. During that time, recognize how often you need or miss it. The habits, skills and character traits you build through this action are more important than the money you save along the way. You need to live the lifestyle and on the budget you later intend to spend. Otherwise you will struggle to stick it.
  4. Do not tell anyone around work about your goals. Not many will understand why you choose not to live the typical earning-spending lifestyle. Therefore think about with whom you share your goals. This will make it much easier.
  5. Increase your range of basic life skills. You do not want to stop working and still be completely reliant on money to cover your needs. The more skills you learn and the more you can provide for yourself, the less money you will need. As basic skills I count gardening and growing your own food. Start with the most expensive ingredients like herbs and then vegetables. Do not start with potatoes. Manually they are a lot more work compared to what they cost at the store. But squashes and berries are easy to grow. Then learn how to repair the items you use and how to maintain your home. With the free time you have there is no excuse not to do most of the work yourself. Learn a skill once and then you can even help out in your community and might even get paid for it. Transportation can also be covered by your own means. Stay in shape and ride your bicycle almost everywhere, adventure into hitch-hiking, etc.
  6. Gather a list of things which you would like to do after you stop working. This will keep you motivated and also serve as a replacement for the time formerly spend working. It will take some time to mentally adjust to the lower pace of life. When you have all the time of the day to yourself, you will probably not always have something to do. Plan for more idle time and prepare your mind with a regular meditation habit. There is nothing more intimidating than being confronted with the task to find a life purpose totally unprepared. This might even lead to depression because you have been thinking, quitting work will make you happier.
  7. Accustom yourself with the thought that you can never plan for all insecurities. As you cannot plan and erase all threads during your working life, likewise you cannot for retirement. The market might develop differently than in the past and this could turn out negatively. You can find comfort in the thought that, if something really big happens, you will not be the only one who is affected. And with the basic and broad range of skills, which you will have acquired until then, you will be much better prepared than the average office worker. Finding work again should be easy and come naturally if you are living amongst and in exchange with other people.
  8. Start developing a greater goal for your life outside of work. The easier task is to keep busy, but it is a greater challenge to find an overall life-goal which is meaningful. A goal that puts the all other activities in context. This is what makes for a successful life. Following a proper life goal will make you grow personally as well.


  1. Working after retirement should be more than finding a job greeting people in Walmart or handing out samples of cheese in your local market. Zoomers Finding Money

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