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To Be Or Not To Be ... Your Own Boss

Updated: Oct 1, 2020

You've been feeling stuck and restless. And no, it's got nothing to do with COVID. Truth is, your work has become dull, the bigger purpose lost, and your future uncertain. For months, you’ve woken up wondering what else you could be doing.

In fact, you already know the answer! You want to be your own boss -- a solopreneur consultant to be precise! But is it foolhardy to quit a stable job in this economy?

No Better Time Than Now

You've had more than a good run as an international business executive. With over 10 to 20 years of company life, growing teams, driving strategic projects, managing change, etc, you could do most of the same with your eyes closed.

Feeling stuck in a rut.

And that's just the problem. It's become humdrum and meaningless. What you want is to feel your adrenalin going again.

Striking out on your own to build and live your professional life the way you want is looking more appealing by the day. Heck, you even went back to school to sharpen your skills with this vague intent to widen your horizons.

The question is: is it the right time?

COVID is hanging over us, you're thinking. Where things are headed in the next few months and years is completely unknown. People with jobs are hanging on tight to them as millions lose theirs. Why would you want to join a mired pit of instability, uncertainty and insecurity?

Well, maybe for that very reason!

Jobs are already precarious but it will become more so as the global economy yo-yos between open and shut. A job today does not guarantee one in six months, a year or two years for that matter.

The point is the world and the job market along with it has become a mired pit whatever happens. Going solo as a professional, if that’s what you really want, is not going to change that. Instead, it might just be the wisest decision you could make for a more secure future for yourself!

The way I see it, 5 good reasons make this as good a time as any to LEAPP – Latitude, Emancipation, Acceleration, Professionalization, Preparation.

1. LATITUDE to jump on new, unimagined opportunities

As economic growth contracts by 3-10%, the jobless numbers are going to climb some more as spend and markets shrink. France reported a historical drop of almost half a million jobs in March. The US has registered over 40 million recently jobless. Downsize, furlough or paycuts, 10-30% of employees are impacted, across startups as well as industry giants like IBM, Uber, Boeing, Sephora or TripAdvisor.

However, no job does not necessarily mean no work! On the contrary. Since companies are culling back, they will actually need skilled or expert talent more than ever – only differently!

Downsizing or hiring freezes won’t mean work completely dries up, not if we want to re-build the economy to some semblance of normal. It just means that companies, big and small, are going to be extremely prudent about paying fixed overheads in the short to medium term.

Where possible, they are going to adopt more agile strategies and approaches i.e. hire when needed, for very specific growth initiatives or expertise, and from anywhere. They’ll want to work with professionals who get this and who see the bigger picture.

Being able to engage, contract and de-contract at reasonably short notice; fulfill a work requisition intermittently as a team, on site, via remote work or all three; know when to step up, step back or step away. A contracted solopreneur who knows how to do all this well, gives companies they work with, the freedom to continue operating and surviving as they find back their footing to re-build for growth.

Sure, you’ll be replacing your boss with clients, but this way, you gain the latitude of broadening your options. Rather than climbing a narrow career ladder defined by others, you’ll be building bridges to shape your own professional opportunities.

2. EMANCIPATION from “contracted workplace stress”

It might seem like COVID’s jobless are being pushed into freelancing or gig work without choice. The truth is for many people, workplaces have turned into disenchanted career land long before COVID.

In a 2017 Gallup study, only 15% of global full-time employees were reported to be engaged, involved and enthusiastic about their job and company. This figure is even more dismal for Western Europeans at 10% and for East Asians at 6%, as compared to their North American counterparts at 33%.

Compare that to 75% of self-employed professionals who profess to be very satisfied with their decision, and about 90% who remain independent by choice. Over 60% say they are less stressed and two-thirds say their quality of life has improved.

For developed economies, the number one cause of absenteeism at work is often stress-related or caused by mental ill health such as depression, anxiety and burnout. Imagine what the workplace ambience is like right now.

Workplace disenchantment

We know for a fact that mental health cases have spiked since social isolation went into effect. Workplace stress probably mirrors similar levels if not more, and there's a high likelihood it will get worse before it gets better -- for as long as markets don't regain some confidence.

People are realizing they have no guarantees of coming out of COVID unscathed. Still, in the bigger scheme of things, independent professionals may actually be better off. Although they’ve seen a huge dip in earnings and client work, they feel more able to cope, having developed entrepreneurial resilience and tenacious creativity.

A solopreneur consultant myself, I also coach others. So believe me when I say I can relate to the sentiment cited in this article. There are many reasons professional solopreneurs don't have the same level of workplace stress. They spread their risks if they work for diverse clients, and they are also free to pick up a gig or diversify their service portfolio as needed.

Salaried executives on the other hand, are tied to their employer, company rules and to management decisions they don’t always agree with or are powerless to change. This inevitably drives up insecurity, feelings of powerlessness, unreasonable stress and fear for the future in an uncertain economy.

3. ACCELERATION to being a mainstay of the economy

The so-called gig economy, combining everything from task-work, part-time jobs, interim contractors to platform freelancers and independent professionals, is almost a US$ 5 trillion market today.

Over 90% of 10 million jobs created between 2005 and 2015 were gigs. In France the rise of freelancers jumped 120% in the same period. Over 30-40% of eligible working age adults in developed economies today are contributors. The market grew by almost 30% in one year at the end of 2017.

Before COVID, market projections placed independent workers at 40% of the global workforce by 2020. With COVID, a UK-based freelance platform registered for April alone, more than a 300% hike in their local market and in Spain. Their Japanese registrations rose more than 500%.

In all this mishmash of data, one thing is clear. Non-regulated white-collar workers now make up more than half the share of generated independent income – many in management, finance, computer engineering, marketing, analytics, design, training or education. Contrary to belief, task workers account for only 10% of independent work in the US.

Gigs are no longer really gigs - at least not in white collar occupations! Almost 40% of companies say their portion of hired freelancers have increased, and will continue to increase (see chart). In an Online Labour Index by Oxford Internet Institute and Oxford University, the fastest growing job segment in the “gig economy” at a rate of 43%, belonged to professional services (e.g. business consulting, accounting, legal).

I'm willing to bet that this market will continue to steadily grow in spite of, and perhaps because of COVID.

4. PROFESSIONALIZATION on several fronts give more credence

For the first time in 2017, solopreneurs or micro-business owners were recognized formally in France as a valid workforce. They were awarded similar health coverage as salaried workers and now enjoy loss-of-job payouts under certain conditions.

Although still far from ideal, this trend will continue to gather momentum in many countries, starting in the EU, as more educated and white-collar professionals strike out on their own. A critical mass will bring about tectonic shifts on three levels.

The first is better understanding. Distinctions will be made between task workers, part-time “giggers”, platform freelancers and professional solopreneurs. With that, we’ll start to see new policies, regulations and protection of worker rights to ensure economic inclusion. There will be an attempt to mitigate the instability of an essential workforce that could easily slide into an informal, marginalized or shadow economy.

COVID has plainly shown how vulnerable or exposed independent workers can be regardless of their status or occupation. More important, it's going to inform and educate policy-makers like no other time to trigger needed change.

The second is the emergence of an industry that will only grow in force to offer solutions targeted at independent workers. In the initial wave, we saw marketplace and matchmaking platforms such as Upwork, Malt, Toptal, etc.

In the early years, these services put clients’ interests first before those of gig workers. Although, this is slowly changing, many solopreneurs are conscious of this downside and are choosing to set up and directly own their client dealings and relationships.

The big shift here is this population that is globally more savvy from a digital and business standpoint. Having honed a reputation for quality and excellence, they will increasingly be looking for the same in services and support to help them mitigate risks and lighten some of their workload in being productive . This is a group who will be looking to professionalize from day one.

As their numbers grow, so will their collective wallet share for innovative, micro services, and their demands as "business buyers". Price points and reliability of such solutions will need to meet professional industry standards in small portions at the same time they delight with agile adoptability and easy usability that are comparable to consumer apps.

The third will be the rise of professional development programs, continuing education and communities of practice designed for this group. Not only will solopreneurs want support to transition and ramp up in practice, but companies will also need to learn how to adapt hiring and collaborating with a contingent workforce on different levels.

Skills at turning knowledge into "products", value-based selling, methodical proposals, cashflow management, marketing, evidence-based analysis, writing and speaking are all going to be critical for solopreneur consultants to survive. Soft skills and qualities such as remote collaboration, negotiation, resilience, boldness, high adaptability, agile multitasking and interpersonal communications will help them thrive. And the more experienced among us will help in showing the way.


As people get more comfortable with different and new ways of contracting, experienced self-employed professionals are likely to see lengthier or more frequent contracting with trusted clients they've built over time. Happier engagements on both sides just make for better partnerships that endure.

Prepare your leap

Although experience takes time to build, there are ways to ramp up intelligently within a dense period of time. The trick is to start now when things are slow or when employers could do with some big picture vision and creative leadership initiative.

You don't even have to put in your resignation as yet. While you are earning a salary, ask yourself two questions.

Firstly, would it be in the interest of your employer to "let you go" right now and "re-hire" you as a consultant or solopreneur after a reasonable lapse in time for what you can offer? If yes, it might give you an advantage for negotiating your departure and payout, as well as securing your first client, all in one go.

The company gets to reduce work charges and still work with a talent they value for a strategic scope of work you choose. In turn, you gain a solid credential and reference for your niche area, and you buy time to develop other prospects.

Secondly, what work can you identify in your immediate ecosystem that you can intervene as a consultant or project manager - internally at your company, or externally with a partner or customer? If it's internal, could you offer to do a short-term stretch project in which you use it as a test ground for your consulting niche, approach or delivery, treating your internal stakeholder as your "client"?

For your company or internal client, you'd be doing something in this difficult times to create value. For your solopreneurship ambition, it would be a chance to learn and to develop your first case reference.

If the opportunity is external, who can you talk with to gather insights and a better understanding to shape a realistic offer? Your creative and entrepreneurial idea may be an added value for your company if you find a way to show what's in it for each party. It could even start off as an intrapreneurship if you play your cards rights.

This new form of contracting is not better or worse. It’s simply different. It frees up both parties from getting in each other’s way to do what’s best for their respective selves, and still engage in a rewarding win-win relationship.

In fact, making it win-win and transparent is the guiding principle here to solid preparedness. Whatever you do, you must ensure it is all above board. Don't infringe ethical practices and create unnecessary confusion with customers or partners. Be smart about respecting boundaries and not undermining your employer.

Building up your independent practice and business will take time, and you are going to need every social capital you've earned to build on, lift off and ramp up. Connections and relationships are your biggest assets for this.

You don't want to burn bridges just when you need goodwill and allies the most. On the other hand, if you are able to turn your current situation fairly to your advantage, you can take back control of your own professional destiny and come out winning – COVID or no COVID.

So, as counter-intuitive as it might seem, this COVID period may actually be the best time to give in to your solopreneur instincts without needing to hand in your resignation just yet. All this may sound like a lot of hard work and strategic think-through, but you knew that already.

After all you were not counting on going solo to escape hard work. You're gunning for something bigger -- a rewarding professional life you can shape and proudly own. Well, it's within reach if you want it bad enough!

Want to know where to kickstart your prep? Take this short quiz to find out and get my practical checklist as someone who's been there. Working directly with me means you'll bypass first-timer mistakes, learn to professionalize your solopreneur consulting and gain unique leverage from Day One!

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