Starting Over Isn’t Easy, Even When You’re Fully Committed

When I wrote the book on starting over it was because I had done it a few times myself and I felt I had conquered the difficult parts, so I wanted to share what I learned. My goal was to make it easy, but even with the best advice there are some parts of the journey that are hard.

Starting over can arrive in very different ways. Sometimes it’s a choice you make with excitement and intention. Other times, starting over is forced on you. It comes through loss, change, disruption, or circumstances you didn’t choose. In those moments, it can feel frightening, disorienting, and overwhelming. 

Even when starting over is something you wanted, once you are actually in it, living it day by day, you begin to realize that it is also hard. The vision may still be clear, but the process can feel heavy. That’s when doubt, loneliness, and fear can creep in, making you question whether you are strong enough to keep going.

I’ve noticed that most of my clients experience one or all of these shifts along the way.

1. Feeling Alone

For many people, the first challenge shows up as loneliness. Change almost always requires separation. You leave behind familiar routines, familiar faces, and familiar spaces. Even when the decision is right, the distance it creates can feel painful. You may find yourself missing conversations, shared history, and the comfort of being known. And when you are building something new, that absence can make you feel like something is missing.

Often, when you start over, you have to leave people, places, and routines behind.

A new job means new coworkers and leaving old coworkers. Retirement means creating a new schedule when you’re no longer getting up and going to work every day. Divorce or death brings loneliness and mourning. Whether you are mourning the actual person, the relationship, or the future you thought you would have, it is still grief.

Research shows that major life transitions such as job changes, retirement, relocation, and loss are among the top causes of emotional stress in everyday life. According to the U.S. Surgeon General, 46% of adults report feeling lonely at some point in their lives, especially during major transitions.

Getting to know new people, learning new places, and buying new things can be exciting. But when all of it happens at once, it can feel isolating. You have to remember, you are not alone. We are starting over together. 

2. You Get Confused

When you are on the path to a new life you designed, confusion can creep in for many different reasons.

You start wondering:

Why does everyone else seem to be going the other way?
Am I doing something wrong?
Did I make the right decision?

Studies on life transitions show that uncertainty is one of the biggest contributors to anxiety and self-doubt. When routines disappear, the brain looks for familiar patterns. When it can’t find them, it assumes something is wrong. You begin to question your choices. You second-guess yourself.

Deep in your heart, you still know what you want. But fear can take over when progress takes time. Keep your ultimate vision top of mind. 

You can use a vision board or a vision video or a single picture, but find something that helps you remember, to remember your dream.

3. Things Feel Too Slow

Another challenge is speed, or what feels like a lack of it.

You expected progress by now.
You expected results.
You expected signs that you were “on track.”

Instead, things feel slow.

According to behavioral research, most people overestimate how quickly change should happen and underestimate how long real transformation takes. Sustainable change often takes months or years, not days or weeks.

When progress feels slow, doubt shows up. What you need in this stage is patience, not panic.

4. You Feel Embarrassed

This one doesn’t get talked about enough. Sometimes starting over feels embarrassing, especially the kind of starting over that’s forced on you. 

People are curious and confused by what’s happening and don’t know how to ask you so they talk behind your back. While others do come right up to you and get in your business. 

You don’t want to explain what you’re doing.
You don’t want the questions.
You don’t want the looks.

Being misunderstood creates resistance.
Resistance creates distance.

So you pull back from people.
You avoid conversations.
You keep things to yourself.

Research shows that fear of judgment is one of the main reasons people isolate during transitions. When people feel uncertain, they often withdraw rather than ask for support. And that makes the journey harder than it needs to be.

Support Makes Starting Over Easier

Starting over does not have to be lonely.

You don’t need a crowd.
You don’t need everyone to understand you.

Even one supportive person can make a difference. In my research I’ve found that people with at least one strong emotional connection are significantly more resilient during major life changes.

That is why community matters.

That is also why I created my private club, Society Rich Girl. It gave me the connection I needed during my own starting over journey. It’s a small group because not many people believe that they can have wealth in all of its forms, but we do. 

So find a group or create one yourself. You don’t have to talk to everyone. But find one person you can talk to. Keep one or two people from your past who support you and share your values. If you don’t have anyone like that, it’s ok. The new people are on their way.

Focus on Milestones

When patience is hard, focus on progress. Ask yourself what’s going well? It doesn’t have to be big. Baby steps count too.

If You Feel Embarrassed, Be Gentle With Yourself

If you feel embarrassed, that’s okay. It happens to the best humans.

It’s an emotion.
It’s temporary.
You will get through it.

The good news is you are aware of it.

Another exercise you can do to get through the hard times is ask yourself:

What is the opposite of embarrassed for me?
Confident?
Proud?
Peaceful?

What would it take to feel that way? 

It may take time to get there but if you continue to keep the connections going, let go of the judgement of others, and pay attention to what’s going well you’ll feel better. You may not enjoy the journey, but you can better understand it. 

If you’re still standing, still trying, still learning, you’re doing better than you think.

Keep going.