Be Your Own Boss – And Be Someone You Want to Work For


In recent years, there has been a tremendous boom in entrepreneurship and self-employment. Some workers have had to make this shift out of necessity – more and more businesses are outsourcing or subcontracting jobs such as customer service, marketing, accounting, etc.

And for many workers, this shift isn’t as much out of necessity as it stems from a long-held dream of independence – working for yourself, setting your own schedule, choosing the projects that appeal to you and passing on those that don’t.

While being self-employed does have many advantages, it does beg one major question – what do you do when you’re self-employed and you don’t like the boss you’re working for?

In this short article, we’ll take a look at some of the pitfalls of self-employment and how to avoid them or how to climb out of them once you’ve fallen in.

Satisfying Your Boss vs Satisfying Yourself

When you are self-employed – freelancing, permalancing, or you’ve started your own company – you are now both the employee and the employer. Now, you have 2 roles that you need to be comfortable in. There are 2 facets of your identity that you need to satisfy.

Hopefully, you won’t be faced with the unenviable task of dealing with an incompetent boss, but you may very well have to deal with a demanding one. In either situation, the best thing you could do is ask for help. 

No one makes it on their own. And that fact is also true when it comes to the self-employed.

In order to satisfy the boss role that you’ve taken on, you will need to do the following:

  • Be a dependable worker
  • Setting your own schedule may sound nice, but the reality is that your workload and your ambition will set your work schedule. This is often the most difficult aspect of self-employment that people struggle with. Set a standard – one that you will be able to sustain – and keep to it. Being dependable is the first step in satisfying “your boss”.
  • Be a productive worker
  • The goals you set for yourself are not up for negotiation. 
  • You may think that because you are self-employed that you won’t have someone looking over your shoulder, stressing about deadlines and your productivity. The harsh truth is that this is not the case. You will have someone constantly looking over your shoulder – you. 
  • The best way to keep those prying eyes from becoming unbearable is by producing results. Be a productive employer and the “boss you” will likely cut you some slack.

In order to satisfy the employee role that you’ve taken on, you will need to do the following:

  • Be a dependable boss
  • The boss sets the expectations along with the rewards for meeting those expectations and the consequences for failing to do so.
  • When those expectations are not well understood, or when those expectations change without warning, this is when feelings of frustration and resentment can set in.
  • Being a dependable boss means being consistent. It’s fair to review and reassess the expectations as the circumstances evolve. But this needs to be done in concert with the employee in you. 
  • Just because the boss is you, that doesn’t mean that you should be expected to sacrifice your work-life balance or any hope of sanity or comfort just to satisfy the “you boss”.
  • Be a productive boss
  • Beyond setting expectations, the role of the boss is to make sure that the employees have the tools and the help they need to meet those expectations.
  • When the “employee you” needs help with a task – better tools, training, etc. – this is when the “boss you” needs to come through.
  • Get the “employee you” all the help they need to perform at the level that is expected.

Set Boundaries and Respect Them

As the boss of a very special employee – you – the temptation would be to let the boss-worker relationship develop to such an extent that it is difficult to see where one role ends and the other begins.

Overstepping boundaries, encroaching upon an employee’s personal space is one of the top signs you work for a narcissistic boss

It is important that you set boundaries. Remember that these boundaries are agreed upon by both parties – the “boss you” and the “employee you”. And these boundaries must be respected by both parties. Any change to these boundaries needs to be agreed upon by both parties and without any duress.

  • Define the days and hours when the “employee you” is not available and should not be contacted.
  • Keep any criticism professional. Any shortcomings at work should not be addressed with personal attacks or criticisms.

Avoid Isolation

When you are self-employed, you are either working for you or having you work for you. In either case, that’s a lot of you in the equation. It’s understandable, then, just how easy it can be after a few months working like that to wake up and find yourself completely isolated.

Here are a few practical tips on how you can avoid getting too isolated, getting smothered by the “2 yous” that are dominating your time and attention.

  • Join a peer group
  • It is easy to find an online group dedicated to people of your profession. Being a member of one such group, interacting with other members, or simply listening to their stories will go a long way toward fighting feelings of isolation.
  • Don’t neglect continual training 
  • Taking a pause on training can often equate to taking a pause on growth. This is synonymous with stagnation. Stagnation has the added effect of boosting negative feelings such as isolation.
  • Share your experiences
  • There is an old adage that says: “It is through giving that we receive our greatest rewards”. Whether it’s by providing online courses or tutorials or simply blogging or sharing your insights on social media, it is important that you share.
  • It is very difficult for someone who shares consistently to suffer from feelings of isolation.

The Long and The Short of It

Being self-employed doesn’t mean you have no boss. It means you are your own boss.

Being a good boss is a skill that you have to work on. It is a skill that you can improve upon as long as you are willing to be honest with yourself, make a fair evaluation of your skills, and be ready to implement any necessary changes.

You may not be the best boss to yourself at first, but the situation can improve by paying attention, identifying areas of weakness, shifting your perspective (empathizing with the “employee” you, and applying the necessary changes to make the “boss you” “employee you” relationship work as best it can.