COVID Career Advice

The pandemic has thrown a lot of people’s roles into uncertainty if not eliminated them entirely. While not everyone will have a choice because of financial or right-to-remain circumstances, it’s a good time to remind yourself that taking charge of your career is still an important aspect of life design. Choices here have effects that reverberate through your current and future quality of life. Play the long game.

There’re 3 things you should be keeping in mind if you’re thinking about a next role:

  1. Take a job for what you will learn
  2. Build a cohesive story around your career arc(s)
  3. Aim for financial independence

1. Learning

I have never taken a role in my adult life for the money.

In fact, in one case, I took a 50% pay cut to move to one of the world’s most expensive cities. Am I unhinged? Do I lack financial literacy? Am I afraid of success? (as an exec I turned down for a well-compensated role once asked me). No. I take jobs to learn.

Optimize for learning. Realize jobs are a portfolio of benefits with pay not always being the most important one. Besides pay and other hard benefits, such as medical, leave, and equity, I advocate that even late-career you should be prioritizing roles tht are going to provide the greatest opportunity for learning. Focus on what you will explicitly learn in your next role. Also, understand how much you’d be willing to trade off financially against certain types of opportunities. A horizontal move optimized for learning at no bump may leave you better off down the road.

I am in awe of a friend of mine who I feel is even better at lifestyle design than I am. She went back after an MBA and stint at Google to get another Masters in an area she’s passionate about and which now is her career. More to the point, she takes her next job based on the job she wants after that one. She is playing chess while I’m playing checkers.

Be wary of firms hiring you for precisely what you did at your last company. Talk about your learning aspirations explicitly with a prospective new employer to link learning and compensation. If they cannot articulate how they intend to train or progress you, you are unlikely to learn much. Firms that can point to skills matrices, progression frameworks, functional mentoring, and explicit training programmes are good. Don’t get distracted by firms offering guaranteed annual increases, bonusing, or unstructured 20% time. If they cannot articulate how this is a larger opportunity or a path for you, you are unlikely to learn much. Be open to the fact that greater scale, geography, reports or similar expansions on your previous role are learning opportunities even if they may make a role just seem larger.

Good companies are willing to invest in their staff and their careers even beyond the company.

Think of your career as a basket of skills. You can go deep and do something better than anyone else in a specialist area, you can have a broad, shallower generalist skillset, or you can do one or two things well and combine them in ways that make you truly unique. Most advice and research on how to really stand out and be valuable point to the latter. If you can, combine two or three skills uncommonly combined that make you a magnet for employers.

Also, think about what skills you would need to be running the whole show - even if that’s not what you want to do. Great leaders delegate so having valuable captains they can give area to makes you incredibly valuable. You’d be shocked at how few core managerial skills most executives running businesses have all the way up to the CEO level (especially in startups). All-rounders are rare. Getting people with all the skills in needed areas are rare, so educate yourself. Continue to learn. Don’t depend on luck and leaning on previous patterns that brought you up sevens in the past.

Besides job-specific skills, add in a focus on a meta-skill every year. Meta-skills are those skills never taught in school that make a big difference in both your roles and your life: decision making, strategy, communicating, negotiating, managing people, and execution. Also, understand how companies work. Try to get an overview and appreciation of how the parts of a company fit together and their functions. Finance, HR, operations, and as well as whatever delivery for projects is required. Being able to contrast and compare these in your career will make you vastly more valuable and ultimately make you more attractive as an employee. Recognize that even bad employers have something to teach you about how not to do something.

And read… Good books. Avoid the fashion of the moment or celebrity biz bios as these tend to be thinly veiled self-help books. Sure, there are some valuable nuggets in there, but you’d be better off reading books surrounding the meta skills I’ve spoken about that are timeless. I’ve got a few suggestions though YMMV.

2. Tell a Story

Few of us have a CV which goes from prep school, to Ivy League, to top tier management consultancy to MBA, then 20 years at a single firm. Yet in some top tier job situations, profiles like that may be attractive to certain Boards and teams. Why? Because they signal an imagined narrative about a person even if it doesn’t really exist.

An alternative, less subscribed story exists where these people lack flexibility and diversity as well as being hothouse flowers, but there is a reason parents and people pay fortunes to get people into top-rated schools. It provides signalling of quality which mot employers would look at as a proxy measure of success.

If your CV is more “non-linear”, you need a story. Be interesting. Explain moves and roles to create logical links in a career arc if an outside observer would have trouble understanding the warp and weft of your history. For example, in my case, I intentionally move roles every 3-5 years and maximized for:

  1. Diversity of experience and geography (so, different industries and countries)
  2. Learning opportunities to round out senior executive and general management experience (MD, CTO, Dir IT, VP Data)
  3. Aimed for roles different life stages and sectors (ie, enterprise, MVP, growth, Series A, unicorn and commercial, NGO, academic, and government)

All my roles have a common thread of living at the crossroads of business, data, and engineering which is perhaps a next challenge; being accountable for corporate functions beyond the purely technical (eg. Marketing or Finance). I also am interested in fundraising and M&A from the company perspective (which was supposed to be something I learned in my last role.).

Your story will of course be different and it’s ok to share setbacks or changes. My story changed enormously when I took a Managing Director role to round out what I saw as a hole in my attractiveness in being an eventual ED for a large non-profit (which was validated by feedback when I lost a top job to another candidate of less, but different experience). That role completely changed my mind about what I should be aiming at career-wise which is something I share with prospective employers when they ask about my sudden shift from the NGO back to the commercial sector.

The key to any good story is to make it cohesive, interesting, and compelling to the listener. Then tie your story to your prospective employer’s.

3. Aim for Financial Independence

Why is financial independence in a post about career advice and job hunting? It fundamentally affects your ability to choose. If you are financially healthy and have an emergency fund, you can take a bit more time about needing a role. You can even go back to school and upskill or self-fund a learning semi-battical. If your finances are not in order, you’re stressed and scrambling for a role or credit in order to keep yourself liquid. FI gives you options and prevents lack of choice.

Think less about a job as a fixture in your life than as a means to an end. Aiming for financial independence and what these jobs can teach you about acquiring assets to make you financially independent of the need for a job or running your own company/ies. Your goal should be independent of working for others and maximizing your flexibility and independence to take roles (or not).

There’s 3 simple rules:

  1. Live within your means
  2. Use credit wisely
  3. Pay yourself first.

It’s not rocket science but it’s incredible how few people have basic financial literacy. The fact basic financial literacy is not taught in schools is a slight failure in our educational system and (for me) a direct result of the fact most education is still based on an Industrial Revolution model of preparing you for a job in the workplace.

So, having a broad understanding of personal finance, budgeting, credit, and investing affects career options.

Live within Your Means

Spend less than you make. Track your finances.

Reduce expenses to make it so that you are living off 80% of your income (including tax liabilities if they are deferred). Aim for reducing your big costs (housing, food, transport) to get there. See my third point on what happens to that other 20%.

Engage in smarter consumerism. Smaller economization can help but ultimately I find they end up making people miserable (eg. cutting coffee). Recognize that we are currently in a time when most people are (effectively) cash-rich but time-poor, so you end up paying a premium (entire businesses, in fact) for convenience. A little planning (and a bit of routine) can prevent you needing to pay these gouges.

For example, cooking at home impressively reduces your food expenditures (if you are time-pressed invest in an InstaPot) and doing something as simple as making your own coffee in the morning and porting it to work in a thermal cup reduced my monthly coffee expenditure 75% (and upgraded my coffee experience significantly since I had great beans delivered home.)

Use credit wisely

The flipside of an advertising industry driving conspicuous consumption and immediate gratification is a credit industry allowing you to move future consumption to the present. You pay for this. A lot. In fact, most people I know that have had financial troubles got in trouble because of credit (primarily credit cards.).

Don’t get me wrong, the wise use of credit allows you choices and independence. It’s not evil. But certain forms are toxic and their business models are based not on providing you with liquidity and choices but on near-predatory credit costs. Credit cards are the worst case, but increasingly, other forms of credit are following suit.

Get out of debt. It’s your most important short-term goal to help you to build confidently. Use debit. If you can, delay purchases. Pay down more quickly if you can (if it’s not penalized.).

Next after that, build a 6 month emergency fund, separate from your main savings in case of unexpected events (I think if a lot of people had these, the COVID-19 crisis would be a lot less dire for many people and families.).

Pay Yourself First

Paying yourself 20% first is sort of a secret royal road to financial independence. Basically, take the 20% left over from the 80% you are living off of and move 20% to a dedicated account or funds (if you are not good at keeping financial tracking separately) for longer term uses.

If you are still dealing with short term debt, Take 10% of that money and use it for accelerated payment for getting out of debt. Once you’ve done that, use the other 10% for a 6 month emergency fund. Sure, your savings will be getting less of a return than debt is costing you, but it’s important to have a liquid buffer of some sort in order to make sure you don’t have to take on more debt.

The goal of the 20% is to use it to build assets. Assets are items that build their own revenue income stream either through direct revenue (in the case of businesses), dividends (equities), real estate (rental income), or appreciation (equities etc). Your short-term goal here is to have your asset returns cover your 80% expenses so that your salary income is all profit, but the most important thing here is to simply start having your money work for you.

What you end up investing in after you pay yourself is up to yourself, your risk profile, and aspirations. Do think about diversification of asset classes to minimize your risk even at larger rates of return. Modern portfolio theory basically shows that there is a rate of return proportional to your risk profile which you can optimize for.

If you want some easy, get-started-now advice without already having a lot of financial knowledge (and I highly recommend educating yourself), I advise opening a no-commission, discount broker account and buying low-cost, non-managed, groups of index funds with your money every month. Most actively managed funds with stock pickers have not outperformed index funds over the long haul.


As people are re-examining their relationship to jobs in the wake of the pandemic, take some time to shut out the noise and focus on the basics of your career beyond a paycheque. Too many people fail to focus on their larger objectives while job hunting particularly if they’re insecure panicked (and a prime source of panic is financial security.).

I genuinely hope this post helped you think if you are being affected job-wise during the pandemic. I’ve given this advice now to a number of people who COVID-19 has not treated well as well as a trio of folks in roles who have been so disappointed by the way their employers have acted during this time, they want to move on. Even people in successful companies

Let me know what you think about the post @awws or