How to Become Self Employed

How to Become Self Employed

How to Become Self Employed

Dr. Lisa Marie Bobby is the founder and clinical director of Growing Self Counseling and Coaching. She's the author of “Exaholics: Breaking Your Addiction to Your Ex Love,” and the host of The Love, Happiness & Success Podcast.

Doing Your Own Thing


Have you been daydreaming about quitting your day job and becoming self-employed? Many people share the fantasy of starting a business or doing their own thing, but can hit a wall when they think about how to actualize their goal of supporting themselves without a job.

How to Become Self-Employed

Starting a business or becoming a freelancer can be very satisfying, and sometimes even lucrative. However, as with anything worth having, these things don't come into existence without intention and a thoughtful plan of action.

It takes time, effort and hard work to build a business or transition into a freelancing lifestyle. It also takes a lot of courage. Many people start businesses only to discover how much work is actually involved. (For example, doing your own thing generally requires many more hours and a great deal more personal inconvenience than a regular nine to five).

However, for some people, the satisfaction that they're working for themselves is worth it. The desire to be independent fuels the fire of successful entrepreneurs, stoking courage, grit, and the willingness to go forward into an uncertain future.

The Emotional Realities of Self-Employment

We often think of cutting the cord and becoming self-employed as a matter of making a decision, putting together a business plan, and then doing it. However, what many freelancers, small business owners and self employed people quickly discover is that the emotional experience of doing your own thing is often the larger, harder obstacle to overcome than the day to day of running a business.

Dealing with the Anxiety of Uncertainty

For example, many self-employed people struggle with anxiety. Not knowing where the next paycheck, or job, or customer is going to come from can be scary. If you're going to do your own thing, you've got to get comfortable with the unknown and out-of-control aspects of being without a regular paycheck. [Tips for managing anxiety, right here].

Overcoming the Overwhelm of Self-Employment

When you work for yourself, feeling overwhelmed is often part of the job description. Everything from designing a marketing strategy to answering the phones to changing lightbulbs to, oh yeah, actually doing the work that you get paid for is now all on you. Developing excellent personal productivity skills are a must if you're going to do everything that really does need to get done.

Coping With Criticism

Many self-employed people who are leaving “safe” careers also often need to deal with the implied or overt criticism of family and friends who want them to take an easier, more predictable path. Even though you believe in yourself, you have to convince others. Entrepreneurs feel like they need to prove themselves; that doing their own thing is not just going to be successful, but way better than other options. This leads to an inner sense of pressure to be successful.

Managing Feelings of Isolation

The pressure to succeed can also lead self-employed people to downplay set-backs, and avoid opening up when they DO feel scared and lost. This need to keep up a strong front may protect them from criticism and needing to reassure worried friends and family (especially parents). But shielding people you care about from the hardships of self-employment can also lead to feelings of lonliness and isolation among freelancers and entrepreneurs who are still in the process of building a business.

For people who are running an established business or are now living their dream as a freelancer, it can still feel lonely. It can be hard to relate to people who have a regular job with paid time off, benefits, and the luxury of clocking out. [Learn more about the importance of vulnerability.]

Cultivating Grit

People sometimes ask me for business advice. I tell them the only thing that I know for sure about starting and running a business, which is, “Throw a bunch of stuff at the wall and see what sticks. Expect that most of it won't. Then do it again.” What I am attempting to communicate is that there is no path to success. We're all making our own way. And, something that every self-employed person has to learn how to cope with is when (not if, friends, but when) things don't work out the way you wanted them to. You have to pick yourself up, figure out what there was to learn from the experience, and then jump back into the fray to try again (with no certainty of success). This type of grit something that every freelancer or entrepreneur needs to have inside of themselves. [More on how to cultivate grit.]

Freelancing Can Pay Off, Emotionally and Financially

However, for many entrepreneurs, small business owners and freelancers, the trade-offs are worth it. Even though the early years are hard, building a sturdy little (or big) business can be very satisfying. Being able to say, “I built this,” can feel more meaningful than working for someone else. For many entrepreneurs and freelancers, even feeling that their success or failure is theirs alone to create is enormously meaningful.

Learn How to Become Self Employed From Someone Who's Done It.

Even though doing your own thing can feel lonely, you're not actually alone. Many people have done it, and you can too. Even better is learning from others about what works, and the things they've done to manage both the planning and execution…. And also the emotional challenges of self employment.

If you want the real deal on what it takes to become successfully self-employed, you're in for a treat. I asked an experienced freelancer, NY-based journalist Michael Stahl, how he cut the cord and started doing what he loved for a living.

Michael shares how he left the security of a great career as a teacher to become self-employed doing something he loved: writing. He's now regularly published in Rolling Stone, Vice, City Lab, Naratively and more, plus he has a book coming out this year.

He shares his advice for how to make the transition from employee to “free” (as well as how to deal with the ensuing anxiety) on this episode of the Love, Happiness and Success Podcast. Listen to his inspiring story and get insight on how to generate a plan, manage the anxiety, and cultivate the grit that will sustain you as you make your own way.

All the best,

Dr. Lisa Marie Bobby

Ps: Here are links to some Michael's work, in case you're curious:


Thoughts on Therapy:

Follow Michael on Twitter (@michaelrstahl) for updates about his forthcoming book, an autobiography about pro baseball player Bartolo Colón

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How to Become Self Employed

by Dr. Lisa Marie Bobby | Love, Happiness & Success

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