Who Do You Want to Be? The Most Important Question!

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“Who do you want to be?” sounds like an awfully deep and existential question for a website to ask.

It sounds more like the kind of question you’d be asked in a philosophy lecture, or as part of a therapy session.

However, it’s a question I increasingly feel like asking many people who get in touch with me, asking for help with their work and business plans.

That’s why I decided to put this article together to explain why “who do you want to be?” is such an important question.

Why do so many people ask the wrong questions?

I was inspired to write this article by some of the queries I receive in my inbox on a daily basis.

It surprises me how many people simply ask something like this:

“I’d really like to work from home. What do you suggest I do?”

This is an impossible question to answer because so many details are missing. The email doesn’t tell me what experience somebody has, what they can do, nor what they actually want to do.

Sometimes the question is more defined; Something like:

“I’d really like to work for myself. I have experience in writing, event coordination, project management and IT support. What do you suggest?”

This at least gives me something to go on! But it’s still very difficult to guide someone based on this. It all raises so many other questions: Did you like doing IT support? Were you good at it? Were you better at coordinating events? Which jobs do you prefer?

Again, this still leaves out the most important questions:

  • What do you actually WANT to do?
  • Who do you want to BE?
Signs showing choices in both directions

“Reverse Engineering” your Desires

Let me give you an example of a question where I’d have a lot more to work with:

“I’ve been a corporate PA for 20 years. I want to spend more time at home near to my children and be my own boss doing the same kind of work. I also love social media and wouldn’t mind getting into that too. What do you suggest?”

This question is completely the other way around.

I could suggest a really clear set of steps for someone in that position, for example:

My whole point here is it always makes most sense to consider “who do you want to be?” and “what do you want to do?” and then work out a plan to get to that point. 

Thinking about what you want is actually quite easy

Written out as above, it all seems so simple and straightforward.

Why would anyone ask “what work can I do?” rather than say “I want to do xxx, how do I go about it?”

In the latter case, there’s almost always an actionable answer.

Want to be a professional photographer? Cool! Take a course, get some practice in, send some photos into some stock photo sites and see how long it takes to sell your first print.

Want to be a blogger? Great! Choose a niche you’re passionate about, read about how to get a blog off the ground, think about a part-time job or some side gigs to tide you over until money starts coming in, and start creating your content.

There’s generally a path to take, whatever you want the end result to be. We live in a world where you can learn new skills for next to nothing. There are online frameworks that let you set up overnight as anything from a craft manufacturer to a taxi driver.

Surely we can’t all just do exactly what we want?

While it’s easy to come up with a path to any career, it is – of course – important to be realistic.

There’d be little point in me deciding to be a professional footballer, for example, even if I really wanted to. I’m overweight, have no coordination and zero tactical skill.

Similarly, and a little closer to home, I’ve often had a dream of being a professional DJ. I’ve dabbled in it here and there and had a few paid gigs, but there are a series of reasons why it would be a bad move for me. First off, I’d get far too involved in the party vibes and end up in rehab in a matter of months! I’d also hate to be away from my small children and kept up late at night other than through choice.

However, there’s still room for manoeuvre in both of those scenarios. The wannabe-footballer could still perhaps find happiness and job satisfaction in being a coach or referee, or in running a football blog or a store selling merchandise; The wannabe-DJ could perhaps look at posting mixes online, curating playlists for hotels, writing for a music website, or collecting and selling limited edition vinyl.

My original point still remains: The best way to make career decisions like these is to work backwards from what you really want and work out a way to get there. For each of us, there’s a point where what we’d do in an ideal world merges with what we can realistically do to earn money in the real world.

And in every case, it starts with that key question: Who do you want to be?

Driver vs. Passenger

Asking for guidance on getting to a goal you’ve decided on for yourself is being a driver.

Asking “what work can I do?” without expressing what you’d actually like to do is being a passenger.

So why are so many of us so conditioned to act like passengers?

This is definitely something I’ve found myself thinking about a lot since starting HomeWorkingClub. Every time I get another “what can I do?” email, I feel more determined to find the answer.

Why don’t people push for what they want?

Having reflected on this a lot, I wonder whether many of us are just victims of our conditioning. Perhaps there’s a part of us that hasn’t quite caught up with the modern, connected world, with its many opportunities. And I say that as someone who’s worked in technology for over 20 years!

Looking back, I remember the act of “looking for a job,” before I went self-employed in 2004. It involved buying a certain newspaper on a certain day to obtain the big “Situations Vacant” supplement. Obviously, this kind of thing has moved online nowadays, but the language alone – “looking for a job” – reveals the approach many take to the activity. It often involves little beyond hoping something comes up where you actually have the skills and experience to apply.

In some geographical areas, I suspect people feel there’s not even as much choice as that; In some provincial communities, it can seem predestined that you and your peers will largely end up working for a small selection of companies in the local area, usually with a clear but unspoken “hierarchy” between them.

It doesn’t have to be that way.

The world has changed a vast amount in just the last 5-10 years.

Nowadays, you can take courses from major global universities from anywhere with an internet connection; You can start selling T-shirts, bags and other merchandise, all over the world, simply by uploading your designs; You can write a bestselling book without needing a publisher.

Is it really as easy as “who do you want to be?”

The short answer is that nothing worthwhile is easy. But I can imagine people reading what I’ve written so far and trying to reconcile it with having commitments, bills to pay and children to feed.

It’s a fair comment, but I do live in that real world too!

Before starting HomeWorkingClub, I was dedicating most of my working time to doing a well-paid consultancy job that was making me increasingly unhappy. It had all started out as a simple freelance writing gig, then evolved into something I never expected. I enjoyed it at certain points, but the rot had well and truly set in by the end.

I had never – at any point – asked myself “who do you want to be?” and replied “an increasingly grumpy and stressed content manager, travelling all the time, dealing with company politics, working in cybersecurity, and selling out most of what I believe in for nothing more than knowing the bills are paid and my son is well-fed.”

Throughout any working life, that fine line between “who do you want to be?” and what you simply have to do to keep your life moving will inevitably shift at times. Sometimes the answer involves having a portfolio career of different activities that all add up to the living you need.

My main point is that those who ask the wrong questions are resigning themselves to always being in the passenger seat. It’s essential to “keep your eyes on the prize,” even during the times you’re making compromises. How can you do that if you’ve not even given yourself the chance to work out what “the prize” is?

When I decided to leave that role, fall back into more diversified freelance work and get HomeWorkingClub up and running, I was WAY more strict with myself:

  • After spending years helping clients build businesses up to eye-watering valuations, I wanted a project that was “all mine.”
  • I wasn’t prepared to do anything involving company politics.
  • I didn’t want to travel too much knowing how much my son missed me.
  • I wanted to spend my evenings cooking and relaxing, not glued to emails and Slack messages.
  • I wanted a blog that could genuinely help people and make a difference.

I’m delighted to now be able to say that I can tick all of those boxes.

I didn’t get everything I wanted; I spent two years training to be a counsellor and found out that completing the training simply wasn’t feasible in terms of time or money with two small children to support; I shelved the idea of a male mental health blog because, on balance, home working was a broader niche where I could see more chance of success. (I still find a way to touch on that interest, however, with articles like this).

So, no, it’s not as simple as just deciding “who do you want to be?” and going for it. But the alternative means not giving yourself any say at all.

Image showing lots of doors to choose from


I’m going to wrap up there because I feel I’m in danger of spoiling a good point by labouring it too much.

I shall end on a quick anecdote:

I had a chat with one of my nephews last week. He’s already sitting on a law degree and is currently studying for his Master’s. He’s someone who truly has the world at his feet – bags of intelligence and so many options of what to do next. Despite that, when I suggested working backwards from a dream of what he’d love to do, rather than doing things the other way around, even he seemed to see it as an outlandish suggestion!

That at least explains why so many people contact me asking “what they can do,” without giving themselves nearly enough of a say.

But it doesn’t need to be like that.