Going From Freelancer to Solopreneur in Your Second Act: Upgrade Your Mindset


A freelancer is someone who gets paid to do what other people need to get done. A solopreneur is a visionary building their own business. Your willingness and ability to define yourself as a solopreneur will be key to creating the kind of autonomy and sustainability you seek in your second-act career.

A freelancer sells their services in a commoditized market, competing on skill, reputation, effectiveness, and price. A solopreneur sells their ability to deliver a transformation, leading their client or customer through challenges to a sought-after state or solution.

The Pros and Cons of Freelancing

On the plus side, being a freelancer allows you to enjoy the freedom of being your own boss, control your workload, choose the clients you want to work with, and have a flexible schedule. No more managers hovering behind your shoulder to pressure you about the deadlines or the KPIs you need to meet. Your success now is measured based directly on the value you deliver and its actual ROI.

In terms of clients, most of them are familiar with freelancing. They know what they want because they’ve seen it before. In fact, many business owners opt for freelancers because they are cheaper to work with (no need to pay health insurance, benefits, etc.).

As a freelancer, you already have a specialty addressing what’s already in the market. Statistics report that around 1.57 billion of the global workforce are freelancers. This means that you compete with thousands, if not millions of people who deliver the same freelance services as you do. Many of your competitors will work for a fraction of what you charge. As such, you’ll need to constantly promote and differentiate yourself to convince potential customers that you fit their requirements – and deserve what you want to get paid. 

The Pros and Cons of Being a Solopreneur

Similar to freelancing, being a solopreneur means starting a business independently. This is an open door to escape the 9 to 5 rat race. The similarities end there.

Solopreneurship gives you the chance to do what you love while delivering a service that brings transformation and makes people’s life easier. 

Freelancers have a systematic way to measure success: they approach customers, embark on a project, complete it in a specific time frame or budget and move on to the next. Solopreneurs take a more strategic approach. They deliver long-term value and measure their success based on the transformation or paradigm shift delivered to their client or customer. 

The challenge of solopreneurship is figuring out an unmet need. You need to address (or maybe even create) your own industry niche and deliver a solution the client doesn’t know how to do. They may not even understand that they need your service until you present them with your value proposition. This requires ample business experience, knowledge, and market research.  It may also require that the client take a leap of faith —  a willingness to accept your potentially new offering – that is not necessarily based on the client’s prior experience. So it might be more difficult to sell. 

Why Being a Freelancer is a Dead End

Freelancing could be a great source of extra income or a temporary solution after losing or leaving a job, but in the long run, it’s not sustainable for professionals who come from a more dynamic background, or who have greater vision or ambition – no matter how old they are! 

First, there is downward pressure on pricing because of too many freelancers giving the same services at a lower rate. In this “race to the bottom,”  companies are allocating lower budgets to outsourcing services. Freelancing has the potential to be a steady source of income but more often than not, your income won’t reflect your experience and knowledge level. 

Second, ageism makes it more difficult to compete. There is a tendency to favor younger people in freelancing, especially if the perception is that new skills, tech platforms, modern approaches, and new paradigms are required (even if this is unfounded in general or in your case!)

The Solopreneur Secret: Adopt a Growth Mindset

The growth mindset concept originates from Carol Dweck’s research at Stanford University. After noticing that some of her students had a positive attitude about failures and continued to learn to improve, others seemed devastated by the smallest setbacks. Dweck began to study these behaviors and beliefs and their effect on individual achievements and life success.

According to Dweck’s research, individuals have two ways of viewing themselves and their capabilities. 

Someone with a growth mindset sees their intellect, skills, and talents as something that can be learned and developed through hard work. Whereas, a person with a fixed mindset believes that the same capabilities are inherent in our minds and cannot be improved over time, as they are something people are born with. The principle can be successfully viewed through the lens of solopreneurship and freelancing. 

A solopreneur, by necessity and disposition, gravitates towards a growth mindset. Their beliefs center around changing and improving the world with intentional action and continuous search for additional value. Whereas a freelancer will gravitate more towards a fixed mindset that relies on setting and maintaining a status quo around selling one or more particular skills or end products. 

A growth mindset is a prerequisite to any creative endeavor, which goes to the heart of solopreneurship. It fosters a desire to learn and strive toward success by displaying resilience in the face of setbacks, embracing challenges, learning from feedback, and driving inspiration from other people’s success stories.

6 Steps to Becoming a Solopreneur 

While each solopreneur will find their own pathway to success, these steps might help you frame the opportunity ahead of you, and get you started on your journey.

1. Choosing Your Business Idea

Good (even great) ideas are a dime a dozen. The challenge is to make the commitment to really vetting them and evaluating their real-world viability as business ventures with upside potential. Think critically at every step in this process. After all, you are trying to set up a business here that is designed to sustain you for years to come.  As you evaluate your business idea, ask yourself: Does it solve a problem? Will people be willing to pay for it? Is it viable? Analyze but don’t overthink! Trust your gut. And trust the gut of people whom you respect to help you arrive at your decision.


 Write down as many solopreneur business ideas as possible in a specific time frame to give a sense of urgency to the task. These could and should include as many of the ideas you’ve collected over time (and more could occur to you as you put your mind to this task). This dedicated kickoff brainstorming session helps you to avoid dwelling too much on any single idea. This will help you take a big-picture look at what you could be doing and hopefully prevent you from committing to what could end up being a dead-end.

Another good way to do this is to use the mind mapping technique. Take your journal or a simple sheet, draw a circle in the middle and write a general idea. Then draw lines and write sub-ideas connected to the first one. Mind mapping is particularly effective for people who think visually.


Establish a set of correlated criteria for narrowing down your ideas. 

Use the Japanese “Ikigai” concept to find the purpose of your new business. This would be the “sweet spot” between what you love doing, what you do well, what you can get paid for, and what the world needs. 


Make sure that what you offer stands on its own. Use the Seth Godin “rule of 10” process to get feedback and help narrow down your idea. This involves finding 10 people who need or want what you could be offering. If after they’ve considered and evaluated your product or service and loved it, you can safely say that you’re on the right track. Conversely, if they don’t like your idea, or even if they kinda/sorta like it (but are not decisively positive), it’s probably best to go back to the drawing board. 

2. Be Authentic, Not Unique

There’s nothing new under the sun. And that’s good for you. When it comes to your solopreneur business, being unique is not the goal — being authentic is. Being unique is a high bar that some businesses attain. But when you think about it, most successful businesses are delivering a version of something that is generally available in the marketplace. The difference is that they offer a particular combination of features that appeal to their particular market.

In the case of your business, look for ways to synthesize all of the special qualities that you bring to the work that you do, from the particular blend of skills and talents that you use, to the influences of your background, identity, and experience, to the personal vision that you have developed about the marketplace, your product or service, and the best ways to serve your clients or customers.

Together these factors make up your “secret sauce.” This is what separates you from your competition, and defines the advantages that make your venture a viable alternative in your marketplace.

3. How Do You Deliver?

Once you settle on a business idea, it’s time to turn your attention to the experience you are providing to your clients or customers. 

While your business itself may not be “unique,” the ways in which you provide and deliver the experience of your product or service will further differentiate you and separate you from your competition.

In a commoditized world, our experience of a product is, in a very real sense, the product we’re buying.

This means that you want to clearly map out your client’s or customer’s journey – from learning about you and your business, to successfully marketing and delivering your product or service, to measuring the success and satisfaction of what you have delivered.

This is another way in which a solopreneur is markedly different from a freelancer. You are responsible not only for what you deliver now but for how that delivery impacts future demand for your product or service.

It might seem counterintuitive, but delivering your product or service is actually the beginning of your solopreneur business journey, not the end.

4. Make it as Close to Turnkey as Possible

A successful solopreneur business needs a roadmap for every key process. As such, you’ll need to document everything beforehand to ensure your business will start to grow from day one.  

Being a solopreneur doesn’t mean you do everything yourself. Ideally, you want to outsource anything that is not within your “zone of genius.” This is the area of focus that represents your vision and long-term goals for growing the business. 

Make your business a repeatable process. Document your SOPs (Standard Operating Procedures). Like a pilot’s pre-flight checklist, have all of your processes and workflows laid out in step-by-step documents that you can hand off to others to execute.

Delegate the repetitive work so that you can do the visionary work. This is another example of what separates the solopreneur from the freelancer. Successful delegation and systematization leverage and amplify your effectiveness as a solopreneur. Operating in this way allows you to stay in front of your business and remain consistently strategic.

5. Dream Big

By continuing to work “on” your business and not “in” your business, you create momentum. You are free to focus on the upside of where your vision is taking you. Many solopreneurs get sidetracked by the day-to-day minutiae of running their businesses. This is particularly true if you are working largely by yourself and have no one to help you maintain your perspective.

This is where your personal Board of Directors could be useful. Even though it’s your solo business, you will be well-served by assembling a small group of advisors to support you. Choose your advisors carefully so that they complement your expertise in areas where you are not as strong. Set regular check-ins and maintain agendas with well-defined goals or Key Performance Indicators (KPIs).

Resist the urge to micromanage. If you find yourself getting bogged down in tasks or follow-ups that are not yet systematized, that’s a sure sign that you need to delegate or re-think your process. Your goal is to always get back to creating the future.

Look for growth opportunities, and trust your outsourced team with increasingly significant tasks while you continue to be the problem finder and the visionary you need to be.

6. Set a Launch Date

Dare to be a solopreneur – even if it’s simply a side gig for now. Think of your “minimum viable product”. Does it have the necessary characteristics to grow over time? If your answer is “yes”, take the leap of faith. 

Resist the temptation to make it perfect or to wait for “the right time” – because there might never be a “right time.”. Don’t let external factors seduce you into procrastinating or overthinking your venture. Action is better than inaction!

You may fail, but you will also learn. And learning is the first step in getting back up and making it work the next time. Motivational speaker Denis Waitley puts it succinctly: “Failure should be our teacher, not our undertaker. Failure is a delay, not defeat. It is a temporary detour, not a dead end.”

Become a Solopreneur (or Entrepreneur), but not a ‘Wantrepreneur’

Depending on your vision, your goals, your personality, and the business you choose, your stint as a solopreneur could evolve into being an entrepreneur. Your business could take off and blossom into a more conventional business that adds full-time staff and grows into a full-blown enterprise.

But no matter how your business grows and evolves, don’t let yourself flounder as a “wantrepreneur.” Don’t let yourself get forever stuck in planning-talking-dreaming mode and never stepping up.

Blow past “analysis paralysis.” If you find yourself stuck at the starting line, do something to get yourself up and running. Hire a coach, join a mastermind group, or find another way to stay accountable for your ideas and ambition. You don’t have time to waste!

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John Tarnoff is an executive and career transition coach, speaker, and author who supports mid and late-career professionals in defining, planning, and achieving more meaningful and sustainable careers.

Fired 39% during his 35 years as a film producer, studio executive and tech entrepreneur, he learned how to turn setbacks into successes in a volatile business. He reinvented his own career at 50, earning a master’s degree in counseling psychology to share his career lessons with others going through similar challenges.

Since leaving entertainment in 2010, John has coached individuals, groups, and led career workshops for university alumni, including for UCLA’s Anderson School of Management. Corporate coaching clients have included Bank of America, Bridgewater Assoc., Levi-Strauss, Softbank, TD Ameritrade, and Thrive Global.

He is the author of the best-selling Boomer Reinvention: How to Create your Dream Career Over 50 and has been named a Top Influencer in Aging by PBS/NextAvenue.


  • Right John on target although you are from a high tax expensive state like California I like your attitude about following the path of a solopreneur over that that I have followed as a freelancer. Why do I mention California because California is not a state that is receptive or encouraging of solopreneurs. Seems like you have to live in a state like Arizona, Texas or Florida to follow that solopreneur path. Then we have the federal government that just signed into law 87,000 IRS agents who willow snooping at your side gig.
    I appreciate the gist of your point about taking the solopreneur path because that will allow you to achieve your highest human potential.

    • Thanks, Phil –
      It’s a bit of a parallel conversation. My main point is about mindset. As I’m describing it, a freelancer is looking to fit their skills into an existing marketplace and compete with others providing the same service. A solopreneur is providing a unique service or package that creates new or enhanced value for the client.

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