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Chapter Eleven

Career Psychology is copyright © Dan Joseph Cavicchio. All rights reserved. No part of this book may be republished, reproduced, or transmitted in any form without the prior written permission of the author. The material in this book is provided solely for informational and educational purposes. It does not substitute for professional counseling or therapy. Information in this book does not represent clinical advice for treatment of psychological disorders.


Chapter Eleven
Self-Employment: A Deeper Look

In the last chapter, we covered the importance of identifying needs and creating products and services to meet those needs. We also explored various ways to market and advertise (or simply communicate about) your offerings.

Let me now share some questions that I've received about self-employment.


Q: I like the idea of being a "digital nomad" and traveling the world with my laptop, doing jobs over the internet. Do you have any thoughts about getting started with that type of business?

A: I know several people who successfully built a roaming freelance practice like you described. It's becoming a very viable form of self-employment.

All the principles that I described earlier are applicable to your situation. You will likely benefit by researching needs and desires of your potential client base, and then creating solutions to meet those needs. Outreach to potential clients and referral sources can be helpful. Even though you're probably considering service-oriented freelancing, you may be able to offer some products that can be delivered digitally as well.

Beyond those basics, I often recommend that my freelance clients become established on platforms like Upwork and Fiverr. These sites match freelancers with companies on a per-project basis. You will need to create a profile, and either "bid" on available projects, or wait for "buyers" to approach you. Feel free to experiment with different pitches, descriptions, and rates.

Once you have established yourself with a few happy clients, you can ask them for referrals. You can also ask if they would serve as references. In time, you might find that you have more work than you can handle.

If you're exploring what types of services to offer, I've included a list of some "careers that can be done remotely" in the last chapter of this book. However, as I mentioned, there is no substitute for having conversations with people about actual needs.

Feel free to ask any business owners you know what they could use help with. Then see if there's a way to help those people while living a digital nomad lifestyle.


Q: I'm a quiet person, and I just don't feel comfortable promoting my business. I'd rather people find their way to me. But I struggle to pay my bills, even though I do have a few happy customers and clients. Is there a way for us quiet people to run a business?

A: Quiet people can certainly run successful businesses. Let me return to the concept of "flipping the script" that I introduced earlier. You might find that this approach is more comfortable than conventional promotion.

As you may remember, when we flip the script, we shift from getting something (in this case, clients and customers) to giving enjoyably.

If you would like to develop a larger customer base, one approach is to increase your giving. Give out helpful information. Give away product samples. Give referrals. Help other business owners. Give and help, rather than push and promote, and see what occurs.

Let's return to Sven the massage therapist as an example. He has a lot of time on his hands. He enjoys giving massages. Here are some ways that he can increase his giving:

  1. He can hand out coupons for free massages.
  2. He can offer a free massage as an auction prize for non- profit fundraisers.
  3. He can put together a website that shares information on various types of massage therapy modalities.
  4. He can create videos demonstrating massage techniques.
  5. He can offer to mentor new graduates of massage therapy programs.
  6. He can give free massages to residents of assisted living homes.

And so on. There are limitless ways for Sven to give. As he fills his days giving, it is extremely likely that the ripple-effects of his generosity will help to grow his business.

He's not looking for quid pro quo arrangements, of course. He's giving freely, without expectation. But it's very likely that the people he gives to will "reflexively empathize" with his generous mindset. These people may very likely feel inspired to help him spread the word about his business.

I find that this giving approach works very well for people who are sensitive, quieter, or otherwise averse to "hype it up" approaches.

You will, of course, need to give in a way that feels comfortable to you. The goal is to find win-win arrangements, and not engage in self-sacrifice. But even a little giving goes a long way.

I encourage you to make a list like I did above, and begin to experiment with different types of giving. As you do that, you might find that your customer base naturally grows.


Q: I'm really not great with accounting and computers and other technical aspects of running a business. Is it even worth trying if you're not technical?

A: I know a large number of non-technical people who are successfully self-employed. Hardly any entrepreneurs I know are accounting gurus. Very few are skilled at IT issues or complex computer systems. So yes, there are certainly ways to run a business without being technically-inclined.

To begin, you will probably want to find an accountant to help you with both finances and various forms of paperwork—licenses and so forth. There are many solo practitioner accountants who are quite affordable.

You also might want to track down a computer person who can help you with websites, email, and other IT-related issues.

After that, you may be all set. Even though there are many technology-related entrepreneurs, the majority of entrepreneurs are not computer-oriented. Musicians, restaurateurs, writers, psychologists, gardeners, interior designers, store owners—few of these entrepreneurs are highly technical.

There is room for all types in the world of self-employment. If you explore some of the needs around you, you may find that many of those needs can be filled by someone who is skilled at creative and artistic solution-finding.


Q: I have a friend who made it big with his business. He always tells me that you have to give 100% if you go into business for yourself. But you're encouraging us to try out self-employment gradually. Who is right?

A: There are endless ways to engage in self-employment. It's up to you to decide what approach feels right for you.

I recommend enjoyable approaches to self-employment because as a therapist, my primary goal is to help people find happiness and a sense of peace. The path of self-employment can serve those goals. Other people have different priorities, and different levels of comfort with investment and risk.

If you do dip your toe in the self-employment waters gradually, you're in good company. It's very common for people to start a self-employment venture as a side job. In the old days, this was called "moonlighting"—working at a second job while the moon was up.

I know many consultants who have conventional full-time employment during the day, and then consult for other companies at night. I know freelancers who hold a part-time or full-time job in addition to their freelance work. Many people have "side gigs" that they run on the weekends. All these are perfectly valid ways to pursue self-employment.

As long as it doesn't threaten your current job (or violate a non-compete agreement), you too can begin to offer a product or service while continuing a normal job. If you start a side business, and it begins to take off, you'll need to decide how much of your time to devote to each of your activities.

Now, I do agree with your friend that larger businesses with multiple employees usually require a deep commitment of time, energy, and attention. You may indeed need to give 100% of your time if you're starting a business like a restaurant or a manufacturing company.

However, there is no rule that you need to aim for a large business. You can walk the self-employment path in whatever way appeals to you. There are countless "solopreneurs" with zero additional employees who have developed extremely robust businesses.


Q: I would actually love to have consultants and employees help me with my business. But I don't have much money to pay them. Do you have any suggestions?

A: There are many win-win arrangements that you can explore if money is tight.

For example, you can offer to pay sales people on contingency or commission. You can offer a partial ownership position in your business. You can offer your service as a "trade," in exchange for a reduced rate for someone else's service. (Though check with an accountant about tax implications on that.)

If you are ready to hire actual employees, you can consider part-time or as-needed work. You are not required to hire people on a full-time basis. If you're comfortable having people work at unusual hours, or on a per-project basis, you might be able to find plenty of people who would like to pick up some extra work.

If you're starting out on a minimal budget, you might want to hire consultants rather than employees—for example, marketing consultants or lead generators who can help you to increase your customer base. Feel free to check out Upwork and Fiverr, which I referenced earlier, to find an abundance of freelancers and consultants.

Seeking creative solutions is key. As I mentioned earlier, this creative problem-solving can be one of the most enjoyable parts of self-employment.


Q: Even though you recommend responding to needs, I'm not sure where to even begin asking people and companies about needs. Do you have some ideas for business ideas to get the ball rolling?

A: Sure. I've created a list of a few dozen business ideas in the last chapter of this book. Note that these types of lists are simply designed to open your mind to possibilities. I believe that your own inner compass will guide you toward options to explore.

Feel free to read through that list, and note if you feel a pull. Then begin to research whether there are needs for that type of business.

The actual conversations you have with people will the best source for business ideas.

Let me conclude the discussion of self-employment by summarizing the major themes that I covered.

Self-employment can be a wonderful journey of learning and growth. There is no real "failure" in self-employment; a business that doesn't make a lot of money can still be a stepping-stone to another part of your career path.

I recommend approaching self-employment with patience. Your first, second, or third business ideas might not "take." It's important to make peace with this in advance, and treat the process as a learning experience. I know several entrepreneurs who tried many business ideas before they found one that hit.

When you're considering business ideas, it's wise to start by assessing the needs of the people and companies around you. What are they needing help with? Where are they stuck? If you can create a business offering to help them, you will likely find a very ready customer base.

You can use the three-dimensional model to expand your vision of what to offer. If you have an idea for a service, is there a product that you can create as well? If you have a concrete offering, is there an ideas-based one you can add to the mix? Might it be helpful to involve consultants, contractors, partners, or employees to help you?

Once you have an offering, you can get the word out both through advertising and through direct outreach to customers and referral sources. Referrers can be extremely powerful. It may be helpful to come up with a list of potential referral sources, and create a custom message for each of them.

Specializations can be extremely valuable. If you specialize in certain areas or niches, it will help people to remember your offerings. It will also give referral sources a pitch to recommend you. You can have many specialties, and expand beyond them. But focusing at first on a handful of unique areas can give your business a boost.

Finding win-win solutions each day is an enjoyable part of self-employment. When you're running your own business, you can continually make "deals" that benefit both you and your customers, clients, employees, suppliers, and anyone else who is touched by your work. Seeking and finding these arrangements can be a fun game.

Let me now move on to the last chapter in this book: a discussion of how to improve your day-to-day work life, whether you're conventionally or self-employed.

click for Chapter Twelve:
Increasing Your Happiness at Work