How To Start a Portfolio Career: 5 Important Steps to Success

portfolio career

A portfolio career is not a new concept, but it has been gaining popularity as technology and the Internet have created many more opportunities to earn income.

What is a Portfolio Career?

A portfolio career is a concept that has been around since the early days of work.

Leonardo Da Vinci is a great example of someone with a portfolio career; by today’s standards, he may even be referred to as a “Polymath” due to having so many different skills and interests that may provide income earning potential.

In a nutshell, a portfolio career is working multiple jobs to create multiple income streams.

The breakdown of these jobs within a portfolio career can be a few different iterations such as:

  • One full-time job plus one or more part-time jobs
  • Multiple part-time jobs
  • A small business in combination with other full-time or part-time jobs

There’s no rule as to what really constitutes a portfolio career.

For example, someone who works multiple low-level part-time jobs because he or she is not skilled to work in a higher-earning full-time position might technically be considered a portfolio career.

But for the sake of this article, I will share with you how to start a portfolio career with the assumption that someday you want to run your own business full-time.

Many businesses are started by entrepreneurs on a part-time basis first while they learn the ins and outs of running a successful business.

If you have a dream, an idea, and the passion to turn it into long-term revenue stream, then starting your business as part of a portfolio career is an effective way to do it.

What are the Pluses and Minuses of a Portfolio Career?

Don’t get it twisted. The life of someone making ends with a portfolio career can be very hectic and stressful, especially when paychecks may not be deposited on a regular basis, unlike having a full-time wage-earning job with a company.

However, the potential for making a seemingly unlimited income while living a life of financial freedom without having a boss breathing down your neck is a chance many people are just crazy enough to take, at least once, in their careers.

For others, a portfolio career is something one falls into after a series of career misfires and failed experiments. I would put myself in this category.

If you’re considering a transition into having a portfolio career, here are the pluses and minuses I’ve come up with from my own experience as a portfolio careerist for the past 7 years of my working career.

Benefits of Having a Portfolio Career

There’s no such thing as “job security” in today’s volatile economy.

I’ve been laid off from multiple jobs in my career. It’s not a great experience, but it’s a reality we all must face.

BENEFIT: No job is ever secure, even if you think you have the gig for life.

Situations change, new competitors pop up overnight, and personnel turns over.

Stop thinking you can’t get a pink slip just because you’ve worked at a place for 10+ years.

In fact, for some companies that might actually help them save money and possibly get far greater value from hiring someone half your age and at half the salary and benefits.

Did I get your attention, now?

Well, that’s just ONE reason why having a portfolio career may be your best option for creating a long-term stream of income to support you and your loved ones.

BENEFIT: Create multiple sources of income and my favorite “passive income”.

I probably don’t need to go in-depth with this one. We all know that living can get expensive as you get older.

But unfortunately, as you get older, you may not be in a position to earn all the income you need from just one job.

And that’s why starting your portfolio career now, while you’re thinking about it, is a GREAT time to begin planning for your future.

Do you want a future of financial freedom and being debt-free while enjoying life playing golf or volunteering at the local animal shelter?

I do!

Granted, there are a few other part-time income-earning sources I’d still do, such as:

BENEFIT: More “freedom”; although if you work a part-time job, you’ll still have a boss.

And if you own your own business, you most likely won’t have anybody above you telling you what to do (unless you have investors) but you will have customers who will dictate what you will do in your business.

Negatives of Portfolio Career

NEGATIVE: Your healthcare/benefits/401(k) and all the other stuff you usually get for “free” from your employer are now all YOUR responsibility. 

Does this scare you away from starting a portfolio career?


Because that means you know it’s a serious issue that you must deal with if you truly think you have what it takes to start your own business.

The unfortunate reality of entrepreneurship

If you can handle the potentially tremendous financial stress you may face having to bear those costs on your own dime, then you have overcome a huge hurdle that trips up a lot of other people and stops dreams dead in their tracks.

Them’s the breaks, kid.

You either play with the hand you’re dealt, or you fold and look for the next best thing.

The choice is yours.

NEGATIVE: You must have self-discipline and motivation to wake up, kick a$$, and repeat every day.

It’s OK. The life of a portfolio career worker is definitely NOT for everyone.

If it was, well…then we’d all be working multiple hustles in hopes of creating a reliable income stream for life.

And that’s exactly what I’ll teach you in this article that draws upon many of my failures, successes, and lessons learned as someone making his living with a portfolio career.

Take my advice or ignore and it do what you want. When you are a portfolio careerist, you make your OWN rules.

But at least give these a quick skim then adjust and apply to your own hustle on the grind.

5 Steps to Starting a Portfolio Career

1. Figure out what type of portfolio career you can start right now.

I’ve held a variety of different jobs in my career, including:

Admittedly, these are all seemingly random jobs upon first glance.

However, upon further inspection…there is a method to my madness.

You see, I’m someone who is easily bored, especially when I feel a job is not getting me closer to achieving my dreams of living a life of financial freedom and time freedom so I can do things like, visit the beautiful city of Boulder, Colorado, which I did recently.

Here’s a video of some awe-inspiring Latin American street fire dancing performed on the Pearl Street Mall, one of the main attractions in the city of Boulder, which is about 30 miles northwest of Denver:

If you have never been to Boulder, Colorado, then I highly recommend you visit at least once. And here’s a handy website that will help you find more fun things to do in Boulder, CO.

2. Find a specialty skill that others are willing to pay for. This may take a long time depending on what you are good at.

Working at so many different types of jobs helped me not only to learn what I love to do (and what I don’t love to do).

I love to teach others useful skills and knowledge that helps them remove the obstacles blocking their path to success.

I think it was working in many different types of job situations that has taught me what makes a good teacher, mentor, and leader.

I’ve had countless bosses and colleagues throughout my career. I remember a few good ones…but mostly I remember the bad ones. They taught me a lot. Mostly what NOT to do.

3. Create your long-term vision and figure out how to achieve it

Do you want to start your own business? Most people do. However, only a small percentage ever try, and an even smaller percentage succeed.

Do you want to be one of the select few who achieve success as a business owner?

By first learning how to run your own business as part of a portfolio career, you will dramatically increase your likelihood for success .

By starting your own business, you are setting your own foundation to creating a successful and thriving company that will provide you and your loved ones with many years of financial security, well-being, and peace of mind.

And that’s what you really want in life, isn’t it?

4. Seek a mentor or someone who will hold you accountable for your plans

Many people are good at starting a new idea, but quickly grow frustrated when the results are not an instant success. Count me among this group of people.

But over the years, I’ve learned that in order to achieve a significant level of success, it’s a requirement that you first fail at least once trying to get there.

That’s because a failure is only a failure if you let it halt your actions from ever progressing further toward your goal.

As long as you are still moving toward your goal, you are not failing.

If you want someone to help you when you feel like a failure and want to quit, then I would like to do a shameless plug and offer my services as a sales and marketing success coach.

Each week, I help a handful of entrepreneurs and rookie small business owners on achieving their goals that will unlock their dream lives.

And if that sounds a bit too good to be true, well…you will just have to try it for yourself to see.

In fact, if you are reading this far, and you are open to the idea of having a person who cares about your future success to hold you accountable for taking actions to achieve it, then send an email to jim (at) and let me know your availability for a free, no-obligation 30-minute phone consultation.

You can help me learn more about your background and where you would like your career and life to be headed, and I will share with you my almost 20 years of knowledge and experience working in corporate America, both as an employee and as an entrepreneur.

Does that sound like a good deal or what?

Well, don’t go running off just yet. I still have one more key to starting a portfolio career, and then I’ll let you hop to it.

Afterall, time is your most valuable asset, and you will never get more of it.

5. Learn how to market yourself

You can create dramatically more opportunities for yourself by getting your name/brand out in front of people who will pay you money in exchange for whatever it is you do.

Sharing your expertise and expressing your unique personality (in a professional sense) via social media, blogs, YouTube videos, or a combination of any and all of these are enough to help you stand head and shoulders over your competition.

And if you run a small business, this is not even a suggestion, it’s a requirement.

Social Media Marketing for Business: Do You Really Need It?

All business owners, regardless of their company size or type, must learn how to use social media marketing to promote your business.

Afterall, isn’t your business your means of financially supporting yourself and your loved ones?

And have you noticed how it seems everyone is looking down at their phones these days, surfing the Web and looking at social media?

Would you agree that it makes sense for your business to be where people are looking the most when they need to make purchasing decisions?

If you feel yourself getting overwhelmed at the prospect of having to learn social media marketing to help promote your business and make more sales…well, you’re right to feel that way.

It’s a monumental task and an extraordinary responsibility that if done right, can lead to a lifetime of income and an endless cascade of excited and jubilant customers and repeat business.

And if your business social media is done badly, well…let’s not even go there. Because I like to think of mainly positive thoughts to create positive outcomes.

Here are two very useful social media marketing resources for business owners:

A Beginner’s Social Media Guide for Small Businesses

How to Master Social Media Marketing for Your Small Business

The Sum Up

Is a portfolio career right for you?

It can be depending on your situation and your vision for long-term happiness.

If you can handle initial hardships such as paying for your own benefits, then you will overcome the major hurdle that stop most people from trying a portfolio career.

The 5 Keys to Starting a Successful Portfolio Career

1. Figure out what type of portfolio career you can start right now.

2. Find a specialty skill that others are willing to pay for. This may take a long time depending on what you are good at.

3. Create your long-term vision and figure out how to achieve it.

4. Seek a mentor or someone who will hold you accountable for your plans.

5. Learn how to market yourself and your business.

Other Helpful Portfolio Career Planning Resources:

Would a Portfolio Career Work for You?

Portrait Of A Portfolio Career: Answer To The “Perfect Job”?

And What Do You Do? 10 Steps to Creating a Portfolio Career

Image: Demi Brooke (CC) 

James K. Kim About James K. Kim
James K. Kim (Jim) is a commercial real estate advisor with Pyramid Brokerage Company of Albany, Inc. in the Capital Region of New York, specializing in helping business owners expand into new locations or sell/lease a commercial retail, office, industrial, or investment property.

3 thoughts on “How To Start a Portfolio Career: 5 Important Steps to Success

  1. Greetings. Saw your discussion on Portfolio Careers. Looks great. I have published a book on the matter called, An Uncommon Way Forward. I have conducted several workshops on the topic in Chicago over the years. As such, I actively structure my employment as a Portfolio Careerist. I am always looking to collaborate with others with same passions for it. Please see my Blog for more on me and my work:

    Would you be interested in chatting sometime about how we might profess its merits together? Best. Peter Willert. 773-230-8817.

    1. Hey Peter,

      Absolutely! I’ll give you a ring shortly and we’ll pencil in a chat on the calendar.

      Thanks for reading and I will check out An Uncommon Way Forward as well, sounds super interesting and helpful for so many people looking for work in today’s tough job marketplace.

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