How to Fail and Still Win Big

Like anyone else before starting a commission-only job in sales, I questioned whether it was the right decision to try it. I’d had a few months experience of a lead generation job, but I’d never made a sale in anything in my whole working career to date.

So I played through a few outcomes in my head. What if I didn’t do very well? What if I made no sales? What if I came out with less earnings than if I just stayed in my current job working at the front desk of a hotel?

I came to the conclusion that it was reasonable that I would find the job very difficult, and there was a chance that some of those outcomes could indeed come true.

But even if I did “fail”, and earn less than what I would have had I stayed in my job at the time, in what areas would I still win? I would probably at least make a few friends, I would have travelled to new parts of the country, I would have learned at least a few transferable skills, and I would surely have practiced overcoming objection. Even if I made the slightly less money than before but still achieved the other things, I would still have counted that as a big win. At the very worst, I would potentially learn to never do a sales job again.

In the end, I did find it even harder than I thought it would be. There were whole workweeks where I didn’t get paid a single cent for my time and effort. At one point in the year, I went 20 working days without making a single sale – not a single commission. But overall, I had some better periods and I ended up making about 1.5x what I would have if I stayed in my hotel job.

What’s even better, as is the nature of commission-sales, I ended up getting better and better over time, meaning in my second year doing the job I ended up earning just over double of what I would have in the hotel. In my third year, I ended up earning about 5x what I would have in the hotel – I doubt the hotel would have given me a 4% increase in my pay within that time, let alone 400%!

The idea of putting yourself out there to potentially “fail” in order to still win big is sort of related to Robert Kiyosaki’s rule of “working to learn, not to earn”, but also can be applied outside of decisions at work too. Failing to hit a 45 minute goal for a 10 km run still means that you completed the race faster than the average runner, and you still get to reap the rewards of the fitness built up through weeks or months of training. Failing in a relationship, but coming out of it learning more about who you are or what kind of partner would suit you the best is still winning big in the long-term.

Which life situations have you flirted with failure and still won big?

The Defining Decade: What People In Their Thirties Regret About Their Twenties

Contemporary culture tells us that our twenties aren’t that important. They’re for experimenting, travelling and generally fucking around. But Meg Jay, author of The Defining Decade disagrees. As a clinical psychologist that mainly sees clients in their twenties and thirties, Jay wrote The Defining Decade to give readers an insight into how important the twenties can be.

The world is changing. Most people in their twenties are graduating from university to find that getting a graduate job in their field isn’t easy. Competition is higher than ever, and it seems more like it’s who you know rather that what you know that determines whether your applications will be seriously considered. As a result, many people in their twenties end up doing jobs that they’re overqualified for – jobs in bars, coffee shops or retail. Jay’s clients who end up in these positions often feel unhappy and disappointed. Too many of these types of jobs for too long can impact our future finances and career. Wages usually peak in our forties so we could be wasting valuable time to increase our earning power.

Jay recommends that people in their twenties focus on increasing their identity capital – the collection of skills, relationships, and professional resources that we build over our lives. This may be through taking a pay cut to work in a lowly job in a lucrative industry, in order to get your foot in the door and work our way up. A simple way summarizing it as Robert Kiyosaki, the author of Rich Dad Poor Dad says, is: “Don’t work to earn, work to learn.”

A common problem Jay encounters while speaking to her clients is that they are anxious because they are comparing their situations to other people on social media. They’ll say “All of my friends are getting married and having babies,” when that is statistically very unlikely. The ones that are doing so might even be people they never talk to anyway, but just happen to be friends on Facebook. It’s important to remember that social media is usually a highlight reel, and even so, comparison is not necessary – what’s important is that you are working towards your own goals, not trying to imitate another’s.

There is a huge discrepancy to how people regard dating in their twenties compared to their thirties. People in their twenties tend to partake in the hook-up culture that has become more normalized over the last few decades. They often go into relationships with people that they know for sure that they won’t end up marrying, but they’re okay with it anyway. When people turn thirty, it can switch like a game of musical chairs when the music stops – everyone ends up pairing up with others, even if they may not be entirely compatible. Jay recommends that people in their twenties be more intentional with their dating so that they don’t have to rush or panic when they start to get a little older.

Jay also warns about the dangers of cohabitation with partners. People in their twenties often move in with their partners because of convenience, or to share financial costs. Before too long, they feel like the next stage is marriage, but they might not really be totally compatible for each other. This is what Jay terms “sliding, not deciding”. Jay recommends if partners are to move in together, to have a conversation about how committed they are to each other and where they see their relationship going in the future.

Another gripe that Jay’s clients often talk about is how their relationships with their family aren’t what they hoped or wished for. Maybe they felt neglected, unloved or unsupported. The good news is though, as an adult they can choose a second family through their partner – getting along with your partner’s family can be a large source of well-being and a sense of belonging.

In a study of people in their twenties, they rated that their most important goal in their life was to be a good parent, followed by having a good marriage, and then a good career. So if people know for sure that they want to have children at some point in their lives, they need to know this: Females become half as fertile from their peak in their twenties at age 30, they are only 25% as fertile at age 35, and 12.5% as fertile at age 40. That’s not to say that people in their thirties and forties cannot have children, but the chances of fertility issues or miscarriages are much more common, and it can be devastating. For men, quality of sperm decreases with age too, although it is not quite as drastic.

The biggest takeaway from Jay in The Defining Decade is that we must do the math on our lives. If we are planning on going to law school and becoming a lawyer, and then want to get married and have three kids after, then what age do you have to start law school? The answer most probably is right now!

For a lot of people reading in their late-twenties or early-thirties, the outlook can seem bleak. But it’s much better to know all this now before it really is too late.