Living With Intention/March Makeover/Self Love/The 6-Week Cleanse

6 Benefits Of Ditching A ‘Milestone Mentality’ Once And For All

By | Tuesday, February 23, 2021


It took me a long time to stop measuring my success in relation to time and age.

Since I was in high school, I had everything mapped out: when I would go to college, when I would get my first job, when I would get married, when I would become a mom, when I should be successful enough to own a house, when I can consider myself successful enough to stop worrying about whether or not I’m successful. 

But — surprise! — my self-imposed, rigid “life plan” was making me deeply unhappy. Some goals I met early, maybe too early. I was promoted to a director role at a women’s website when I was 26 only to take a much junior job four years later. I bought a house with savings and acquisition money from said women’s website when I was 29. I married young, but we still haven’t decided on becoming parents or not. My life felt (and still feels) all over the place, as though there’s a glitch in the algorithm I coded for myself.

By the end of 2020, I decided to accept the unknown and that there were some goals that would need to go back to the drawing board, put on pause, or discarded altogether. My personal KPIs were fixed when life was not. And life is fluid — you gain, you lose, you start all over again, you hope your hard work pays off and that you’re in the right place at the right time (sometimes you are, sometimes you’re not). I’ve been slowly allowing myself to become a lot more flexible with my expectations because I realized that my original goals didn’t allow for errors, delays (or pandemics, for that matter). And that was unrealistic because most of us are going to run into roadblocks, mistakes, miscalculations, and impromptu decisions.

To avoid feeling the stress of not meeting set-in-place milestones, here’s why you should replace them with a more flexible path to success and happiness.

1. You’ll have a healthier relationship with age

I was depressed when I turned 30. It was the beginning of summer in the middle of a pandemic, and I was unemployed. Not only was I spending the first day of my 30th year in my pajamas and eating whatever takeout was available that I could afford, but I was spending the first day of my 30th year feeling like a disaster. I was supposed to feel good about turning 30! This was going to be my year! I was supposed to have a lucrative career and start thinking about getting pregnant! I was 30, and my life didn’t look like what I had projected for myself, and it took a while for me to accept that, and understand that age isn’t a correlation to success, nor is it an indicator of future success. There are ups and downs, and this was a down. And that’s normal.

When you stop tying goals to age, you feel less animosity toward getting older. I’ve stopped worrying about how “successful” I’m supposed to be by X age and I’ve swapped that with evaluating whether or not I’m happy and handling stress and anxiety in healthier ways. Age isn’t even factored in.

2. You give yourself more potential for happiness

When you don’t give your goals and personal deadlines any wiggle room, there’s the tendency to feel shitty about yourself. And you shouldn’t feel that way, especially if you’re working hard, giving your career, hobbies, and relationships everything you can so they bloom and become as fulfilling as possible and trying to take care of yourself. If it’s taking longer than you’d hope to save up for a down payment on a house or car, or if that investment didn’t pan out like you’d hoped, or if you and your partner decided to call it quits, it’s okay to be kind to yourself. 

3. You can stop putting so much unnecessary pressure on yourself

Many of us grew up with demanding parents who expected a lot from us. I did; my parents pressured me my entire life, telling me that if I didn’t become a doctor, I’d have to accept defeat and lose out on success, comfort, and prestige. They pushed and pushed and pushed, but I went another direction. Not that this stopped the pressure — after I graduated college with an English degree, I just put it on myself. I still expect a lot from myself on a daily basis, but I also have learned to cut myself some slack. I ask for extensions. I take breaks. And by doing this, I don’t feel like I’m about to break at any given second.

4. You get more freedom

When you give yourself tight goals with deadlines that are connected to age or time, you might lose out on opportunities. For instance, maybe your dream career path doesn’t allow you to take a risk and start your own consulting business (even if you think you’d actually be great at it). Or your idea of a perfect family is stopping you from ending a toxic relationship. When you subscribe to a milestone mentality, you can’t take as many risks or have as much freedom to try different things. But when you do take a chance (or several), you’re missing out on finding success and happiness in other ways you hadn’t explored yet.

5. You can stop comparing yourself to other people, already

If you want to meet certain milestones by a certain age, it’s likely that you’re looking around and observing how others have done. Lately, I’ve seen a lot of coverage around CEOs in their early 20s and their success stories. It’s awesome to achieve a lot when you’re young, but it’s totally okay if that doesn’t happen, either. Focus on your life and your own pace, and worry less about others. You have no idea what help they received, connections they have, or luck they stumbled upon. I’m not saying that all 22-year-old unicorn startup geniuses who become billionaires overnight had a leg up, but there’s a lot of background that’s untold when we’re spoon-fed these glamorous and aspiring stories. We also don’t know if these individuals are truly happy or healthy. We have no idea.

And regardless, you should construct your own definition of success — not someone else’s. You’re no less amazing if you didn’t create the next billion-dollar tech company in your basement, promise.

6. And you can definitely stop feeling bad about all those 30 under 30 and 40 under 40 lists

I think we can all collectively agree that we can go ahead and unsubscribe to X under X lists. It’s awesome to celebrate people for their achievements, but it’s not awesome to put an age deadline on those achievements. 

Ditching a milestone mentality doesn’t mean you can’t set goals for yourself — you totally can and should! But instead of posing a goal as something you need to meet before you turn X age or in X years, allow yourself some space, time, and room for changes.

Gina Vaynshteyn is an editor and writer who lives in LA. You can find more of her words on Refinery29, Apartment Therapy, HelloGiggles, Distractify, and others. If you wanna, you can follow her on Instagram or Twitter.

Images via Unsplash

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