When Is It Time To Start Investing In Yourself?

Is there something you’re avoiding doing for yourself at the moment? Is it saving and growing your money, spending time researching for your next project, or finally seeking out resources to help you take the next step forward in your life, career, or art? Is there something that’s been on the back burner for you — perhaps a seemingly innocuous thing, like waiting to introduce yourself on that networking thread or putting off enrolling in an investment course for another cycle?

In case you’re wondering, no, these aren’t random examples. Each one represents a situation I’ve found myself in just this year with little idea of how to shift things. I’ve found that the closer one of these steps comes to my personal benefit, something that no one needs or has asked me to do, the harder it is to find a way to move toward it.

“Is there something you’re avoiding doing for yourself at the moment?”

At first, the barrier might appear to be time. A scheduling conflict, say. And then money. Is it worth it? Shouldn’t I save it or spend it on something more…essential? And, of course, there’s the question of energy.

All of these resources are in too short supply — but consider what it would take for circumstances to change. Sure, some deus ex machina might come roaring in and change the course of your life. More likely, it’s a mindset shift that is necessary to reallocate resources from the current configuration that keeps everything holding together to something new that expands your reality and welcomes in change and growth.

While it may seem like only a small shift is needed, the reasons why we avoid investing in ourselves can be thoroughgoing.  (If Just sign up for the class! worked, we’d all be experts.) So let’s work through what exactly the blocks are to help loosen things up a bit, before considering when and how to make the leap and start investing in yourself. ✨

Why women hesitate to invest in themselves:

For many of us, investing in ourselves can feel like an indulgence or a step too far. Everyone’s subject to self-doubt — but for women, the reasons to avoid investing in themselves are amplified by cultural expectations. Some of the reasons that come up frequently include guilt, doubt, avoidance of attention, a tendency to seek permission, and fear of success. Am I missing others? Let me know if the comments.

“Some of the reasons that come up frequently include guilt, doubt, avoidance of attention, a tendency to seek permission, and fear of success.”

Each of these could take up the space of a novella, but for me, I’ve found I experience a dastardly combination of them all. Most clearly, I fear that striking out on my own and going after my wants precipitates a fear that I’ll be left high and dry, without the support of others who would prefer that I either work for them or, at least, don’t outstrip them. This is, of course, a fantasy — but it’s no less real for that. It is very real in the sense that it prevents me from moving forward in areas that are meaningful to me. The important thing here is to interrogate your own particular reasons for not investing in yourself and take the time to articulate how they show up for you in your life.

What do you imagine would happen if you spent minutes, hours, money, etc. on your private pursuits? It might be helpful to talk it over with a therapist, a friend, or journal about what comes to mind. The more conscious you are of your hang-ups, the less power they’ll have over you.

Why should you invest in yourself?

Well, there’s no good reason not to! And counter to what you might fear, a whole slew of benefits can come along with building towards your passions, skills, and security — from enjoying a sense of purpose to having better relationships, a stronger mentality in the face of adversity, and overall wellbeing. Devoting yourself to your pursuits will transform your present and your future — and even the way the world works. Seriously. This isn’t just about feeling better, it is about making space for your contribution to the world. No matter the scale — whether you change the dynamic in a local organization or make waves around the world — it is important that you cultivate your gifts.

No one is going to do it for you — because no one can.

“No one is going to do it for you — because no one can.”

So, when should you invest in yourself?

If you’ve made it this far, then you know this isn’t an easy question to answer. Deciding when to invest in yourself is about walking a fine line between recognizing when you’re ready but not waiting for everything to perfectly line up. Investing in yourself before you do the work to understand your hesitations might plant you right back where you started in the land of qualifying statements and false starts. On the other hand, there’s no universally perfect time to start. It’s a question only you can answer. My best advice? Once you feel that desire for change or growth, that’s your sign.

How to start investing in yourself:

If the idea of prioritizing yourself still feels daunting — or even a little rebellious — that’s okay. Here’s a list of practical tips for centering your desire, and I encourage you to return to it as you’re navigating your way towards finding more conviction and resolve around your own direction.

1. Begin by holding empty time with yourself

Set aside time, even 5 minutes a day, for yourself with nothing planned. When you arrive at this time, take stock of what is calling out to you. Treat this time with the same respect you would any other appointment. Take note of your success in keeping the appointment, and how others around you react. This will start as a kind of test drive before you gradually build to longer durations and plan to fill it with longer-term projects.

2. Start a “me fund”

Even if it’s $5 or $10 a week, begin saving towards a dedicated fund to support your own growth or joy. This could cover a new class, coaching, a retreat, or simply things that bring you happiness that you wouldn’t normally buy for yourself. Do you love food? Interior design? Vintage clothing? Browse, buy, and dive deep on something that sparks your creativity.

3. Say yes to curiosity

Is there a class you want to take, a new skill you want to try, or even an old movie you’ve always wanted to watch? Give yourself permission to say “yes” to exploration, even if you aren’t sure where it will lead. Don’t ask for permission (or try not to!) and don’t worry if it ends up not working out. Embracing your natural curiosity is nothing to be ashamed of — and feeling less precious around your ideas and impulses is a great path to growth.

4. Find your people

Surround yourself with those who cheer you on. This could be a mentorship circle, a book club, or simply a friend who also wants to put herself first. Don’t feel pressure to share your new pursuits with anyone who drags you down, and focus on building community with others who get it. 

5. Return to your “why”

Instead of seeing self-investment as a selfish act, remember that it is a radical act of love and care for yourself. The positive impact extends to your family, friends, and your wider community too — but let’s not worry too much about that for now. When you focus on your growth, you’ll realize that you’re able to open doors for others in your life too.


Do you make time to invest in yourself? Have you had to “do the work” to get there? Let us know in the comments where you’ve found value in the process — or what you’re hoping to achieve. This can be the place where you begin.


Ashley D’Arcy is the Senior Editor at The Good Trade. She holds an MA in Philosophy from The New School for Social Research and has contributed to esteemed outlets such as The Nation, 032c, and Yale School of Management’s Insights where she’s leveraged her expertise in making complex ideas accessible to a broad audience. In addition to her editorial work, she is training as a psychoanalytic mental health professional and provides care to patients in New York City. Ashley also explores sustainable fashion, clean beauty, and wellness trends, combining thoughtful cultural critiques with a commitment to mindful living.


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