Going Freelance – 7 Steps to Career Independence


Going freelance was not the plan. You were supposed to stay in that job you loved for as long as you were performing well. Instead, you got laid off in your 50s, a notoriously difficult age to find a new job.

Many of us over 50 have worked in steady and stable jobs and companies for a decade or more. Losing the regularity and the security of steady employment is particularly tough in an ageist economy. But going freelance seems even stranger and riskier because it’s truly unknown territory for someone who’s been employed for so long. Why not just tough it out and wait and hope to find a new job?

Unfortunately, the odds are against you. It’s a hard truth but so many people our age are experiencing it. Wages are down all across this economy, and when you factor ageism into the mix, you’re unlikely to be offered a desirable job that will pay close to what you used to make.

In an earlier post about the mindset around your job search I proposed that you think of yourself as a consultant providing value to a client vs an employee taking directions from a supervisor. For this post, I’m going to suggest you consider seven areas of focus that will help you consider andor develop a potential freelance business. These mindset shifts will serve you well whether you forge your way into your own freelance career, or go back and find a new job that serves your agenda and meets your needs.

Nothing to Lose/Everything to Gain

Before you push back and declare that freelancing isn’t for you, stop for a minute and consider the pros and cons. You can spend just so many hours a day looking for a new job. What are you going to do after you’ve sent out all the resumes, called or emailed all of your connections, and scanned the web for new job postings? Instead of staring at your empty email inbox for the rest of the day (or distracting yourself on social media), you could be starting a business.

Exploring what’s possible will expand your mind and help you think of yourself in new ways. Even if you’ve never thought of yourself as a freelancer, use this opportunity to “act as-if” and imagine what your day and your life would be like if you made this shift.

There’s no downside to this experiment, and if it does indeed lead somewhere, you will have sown the seeds of a perhaps unexpected success.

If you decide that you’re not ready to completely change direction, think about starting a side business (aka a “side gig”) to dip your toe in the water and build some traction without feeling like you’re making a total leap into the unknown.

Going Freelance has Pros & Cons

Being your own boss, setting your own schedule, and designing the business the way you want certainly sounds appealing, but of course, it’s not all a bed of roses. Among other things,

  • You’ll have to cover your own health insurance (could be a big deal),
  • It can feel lonely and isolated if you’re used to a big bustling office, and
  • It’s going to take you some time to build that business up to where you’re making at least the same money as in your old job.

Now is a great time in your life to be doing something like this. I know that sounds strange to many of you because you many be feeing discouraged.  But here’s the truth of it. You know more than you’ve ever known about your field. Arguably, you’re an expert and a wizard at doing at least one important piece of business extremely well. In fact, if you could work in a job that just let you do what you do best, you’d be in heaven. So maybe that’s why you should consider freelancing. As the Kauffman Foundation reports, older business owners and entrepreneurs have many advantages over younger business-starters, and are more successfull in the businesses they launch.

1. Your Priorities: Deciding What You Want Out Of Life

Like any professional project, you have to start with research and due diligence. You need to figure out what you want out of your life. Your work is only part of it. Look at the treadmill of obligations and interconnected commitments to job and family that have kept you in one place for so long.

Disentangling yourself from those commitments can be a big deal and you should approach any big life transition like this with caution. If you decide that there is freelancing scenario that could make sense, look at pivoting gradually by doing the necessary research, seeking out advice from people in that field, and talking to professional business advisors (the U.S. Small Business Association offers business coaching services…). Creating a sound financial plan is crucial so you budget your money wisely.

While any transition is full of uncertainty, the more planning and contingencies you build into the process, the less stress you’ll put yourself through (while making it easier on your family and friends).


Source: Unsplash

2. Your Role: It’s Time to Be Creative

One common experience I hear about from many of my clients over 50 is that they’re tired of just following directions and taking orders. The team or company direction may have changed significantly since you’ve been there, which can be discouraging and disillusioning. Perhaps more importantly, you’ve gotten enough experience under your belt where you have your own ideas about how things should be run.

You’ve likely graduated to what I like to think of as a more creative role. I don’t mean creative strictly in an artistic sense. To me, creative also means innovative, risk-taking, experimental, and just generally open to new ways of getting things done.

It’s time to think of yourself as someone who defines the problems that need to be solved, drills down to the broken aspects of a business that need fixing, and understands how to take responsibility for all of it.  After decades on the job, you are finally that person you always saw yourself becoming.

Your creativity draws on the skills that you have, but it goes beyond your skills. You understand how to cut through obstacles and get right to the heart of the matter. It is an expression of everything you’ve learned in your career and in your life, i.e. it’s the wisdom of your age.

3. Your Business: The Magic is in the Niche

Every client I have ever worked with has struggled with this dilemma (full disclosure: I struggle with it, too).

Product and marketing gurus are always talking about focusing on a single solution, a niche market, even if your tendency is to want to address a problem that is common to millions of people. It seems counter-intuitive to commit to a niche business.

“How can that be successful? Shouldn’t I go broad to capture as many people as possible? Surely, if I offer a range of products and/or services? I’ll be casting a wider net and will surely capture more prospects.”

It sounds smart, but the reality works in reverse. Customers are not generalists. They know what their problem is, and they’re looking for an answer and a solution to that problem. If you come across a customer who can’t decide what their problem is, or what their most pressing problem is, it’s not your job to clarify it for them. You will fail because until they figure it out for themselves, they won’t ever believe that they need you.

You want to go as narrow and as deep as you possibly can. You want to be the most complete and comprehensive answer and solution to the one biggest problem that your market will have. Figuring that out and holding up a sign that says “Buy Here” is the key to launching a successful business. This is more true than ever in a digital economy where you have immediate access to scale your product or service to the entire planet.

4. Your Infrastructure: Overcoming the Tech

In the digital economy, going freelance opens up myriad opportunities to connect with customers, but it also presents gargantuan-seeming infrastructure and startup challenges. If your most intimate brush with technology has been calling the IT guy at work, you are in for a bit of a learning curve. But if millions of people of all ages and backgrounds can figure it out, so can you. There are limitless resources available to you – starting with free instructional videos on YouTube to more comprehensive paid courses on LinkedIn Learning about anything you want to learn more about.

And yes, you need a website. There’s just no way around this. Your social media presence is not enough. Anyone on LinkedIn with a real business (more on LI below) also has their own website. It truly is your storefront. It doesn’t have to be complicated. And the site creation tools make it remarkably cheap, quick and easy to launch (for you if you’re a DIYer, or for your web designer)

Take it in steps and in stages. The more you do, the more you’ll learn, and the more you’ll know. One way to get the support you’ll need in the tech area is to join groups, including on Facebook, or subscribing to people’s Channels on YouTube. Search Google for relevant information sites and sign up for newsletters. There are amazing resources available to you!

5. Your Lead Generation: Update Your LinkedIn Profile

If you get an offer or a lead because a recruiter discovers you on LinkedIn, it’s going to be because you have a clear, compelling, engaging, and specific definition of what you offer, and why it’s valuable.

LinkedIn is more than an online resume.  If you limit your profile to talking about what you’ve done, you’re missing a huge opportunity. LinkedIn is valuable because it gives you an opportunity to also talk about who you are and what you want to do. Sell a little. Be aspirational. Be visionary. Don’t be dry or corporate or too salesy. Connect with people on a personal level. Appropriate transparency is part of being professional in the digital era.

6. Your Prospects: Use Networking to Meet Your Tribe

Once you’ve got your LinkedIn profile in good shape, you’ll want to leverage that with online and in-person networking. Most people (me included!) find networking events anxiety-producing. It’s the same feeling as going to a dance in junior high school. But it can really help you to promote your business, and to meet new people.

Your success will come in direct proportion to the number of people you connect with, and the number of people you can incorporate into your tribe. Your tribe are the people who naturally understand you, who have similar goals in mind, and share similar values, mindsets, and strategies. They’re the people who will help promote you and your business or your value proposition.

Whether you’re actually trying to launch a business or a consultancy – or trying to land a job based on a well-defined value proposition and service offering – your tribe is how you’ll accomplish that goal. More and more, niche event businesses are popping up around making networking and tribe-building an easier, friendlier idea. Check out this one as an example: https://corp.designstudio.com. You’ll find similar groups in your area. Everyone realizes that local in-person connections are important to initiating and building real business relationships.

7. Your Methodology: Build New Success Habits

Sustaining the momentum around a freelance business or a new value proposition or professional identity can be exhausting. It is truly pulling yourself out of your comfort zone and you could wind up feeling vulnerable and unsure as time passes without measurable results. Don’t give up! This will take time.

Instead, look at building new habits around your new business practices to support you in what will be your eventual success. Persistence is key! You’ve probably browsed the virtual stacks on Amazon overwhelmed by the proliferation of self-help and business productivity quick fixes. A few authors stand out. Check Charless Duhigg, the writer of the now-classic The Power of Habit, as well as James Clear, whose Atomic Habits is a worthy alternative approach. The most impressive book on productivity that I’ve read in recent years is Cal Newport’s Deep Work. It makes a great case for the value of sharp focus, and the reduction and abolition of the digital distractions that can keep us from executing on our plans and our dreams – like starting a freelance business!

Enjoy It!

While your tendency may be to look back at the job you lost or the corporate family that you’re missing, you’ll fare a lot better if you look to the future as a new adventure and a new life stage. Meeting life’s challenges with optimism and confidence has been shown to increase life expectancy and improve your overall health. It may take some time to wake up each day fully invested in that new understanding and appreciation, but you’ve never been in a better place to make that into your next reality.

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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.


  • John, I appreciate your words of wisdom. How would you recommend doing the LinkedIn profile for side hustle Freelance work that will replace the 25 year chapter 1 work life. I want to drive this career into chapter 2 and plan to change before it happens to me. I hope this makes sense.

    • Thanks, Michael –

      I’ve got a few ideas – it’s a really great question. And it’s one that I think a lot of people are curious about. Let me ponder and put something together as an email blast to the list. You’ll see it there!

  • your words are gospel, never let people bully you with there timelines for success. networking colloberation and moxie will give you the competitive edge. I am not just making a post, chanting from experience. i went from success to rock bottom, losing everything but gain the best gift honesty and authenticity. sholom.sandford

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