10 Questions to Ask Before Losing Weight

Reviewed By Danielle Glesne, RDN, LD, CDCES

As the New Year approaches, many people naturally start thinking about weight loss.

While the desire to feel better in your body is understandable—and often healthy—how you approach weight loss matters just as much as the goal itself.

Before jumping into another diet, challenge, “detox” or “reset,” pause and ask yourself these 10 important questions. They’re designed to help you reflect on past experiences, avoid common pitfalls, and pursue weight loss in a way that’s sustainable, realistic, and life-giving.

Let’s go…

1. Why Do I Want to Lose Weight?

This is the most important question of all.

Weight loss itself is rarely the true goal. More often, it’s a pathway to something deeper—more energy, better health, greater confidence, improved stamina, or being a better example for your family.

If your “why” is strong enough, it will carry you through the hard parts. Weight loss is rarely linear or easy, so staying tethered to meaningful reasons—faith, family, health, or quality of life—makes all the difference.

2. What Made My Previous Attempts Unsustainable?

If you’re trying to lose weight again, that’s a strong signal that past methods weren’t sustainable.

Ask yourself:

  • Was the plan overly restrictive?

  • Did it eliminate entire food groups?

  • Did it demonize certain nutrients?

  • Did it rely on willpower alone?

Extreme calorie limits, rigid food rules, and “never eat this again” approaches often work short-term but fail long-term. Understanding why previous attempts didn’t stick helps you avoid repeating the same cycle.

3. What Am I Going to Do Differently This Time?

Doing the same thing and expecting different results rarely works.

If you lost weight before but regained it, ask:

  • What didn’t actually change long-term?

  • Did I have guidance or accountability?

  • Did I learn long-term skills—or just follow short-term rules?

Many people have tried countless diets but never worked with a coach or learned how to build flexible, personalized habits. Real change usually requires a new approach, not just a renewed burst of motivation.

4. Can I Commit to a Reasonable Timeline?

Sustainable fat loss is not fast—it’s steady.

For most people, healthy weight loss looks like 0.5—1.5 pounds per week. While slower than crash diets, this pace dramatically increases your chances of keeping the weight off.

If you’ve been trying to lose the same 20 pounds year after year after year, committing at least 20–40 weeks to do it right may actually save you time in the long run.

5. What Will I Do When I “Mess Up”?

The idea of being “on” or “off” a diet is exhausting—and unnecessary.

Weight loss isn’t about perfection. There is no falling off, only learning and moving forward. One high-calorie meal, weekend, or holiday doesn’t undo your progress unless you let it spiral into guilt and quitting.

Ask yourself:

  • Will I punish myself—or get curious and adjust?

  • Can I see setbacks as data, not failure?

6. What Will I Do If My Progress Stalls?

Weight loss is never a straight line.

Daily and weekly fluctuations are normal and healthy. Plateaus happen for many reasons—water retention, stress, hormones, sleep, digestion—not just calories.

If the scale stalls, will you:

  • Assume your body is broken?

  • Slash calories further?

  • Give up?

  • Or adjust thoughtfully and patiently?

Having a plan for stalls prevents frustration from turning into quitting.

7. Do I Have a Truly Sustainable Plan?

Many people eat one way to lose weight and another way to live—and that gap is where weight regain happens.

If your plan feels miserable, rigid, or temporary, it’s not sustainable.

A better approach is using the weight loss phase to learn how you want to eat long-term, based on your preferences, lifestyle, and values—not someone else’s meal plan.

8. Do I Have an Exit Plan?

Weight loss should be a season, not a permanent state.

Ask yourself:

  • What happens when I reach my goal?

  • How will I transition into maintenance?

Without an exit plan, most people revert to old habits because the diet itself was never meant to last. A clear transition from fat loss to maintenance is essential for long-term success.

9. Do I Know How to Maintain My Weight?

Most people know how to lose weight.

Very few know how to maintain it.

If you find yourself losing the same weight year after year—decade after decade—the missing piece isn’t more discipline, it’s maintenance skills.

Maintenance should feel similar to how you ate while losing weight, not like abandoning everything that worked. Learning this skill is often the difference between temporary success and lasting change.

10. Do I Have the Right Support in Place?

Weight loss doesn’t happen in a vacuum.

Support matters:

  • A supportive spouse or family

  • Friends who respect your goals

  • Environments that don’t sabotage you

  • Or a coach who guides, challenges, and encourages you

For many people, having a knowledgeable, empathetic coach is the single biggest difference between repeated failure and lasting success.

Final Thoughts

Before starting another weight loss attempt, take time to reflect. These questions aren’t meant to discourage you—they’re meant to encourage you to approach weight loss with clarity, intention, and wisdom.

Sustainable weight loss isn’t about fad diets, challenges, fake detoxes, or quick fixes. It’s about learning how your body works, building flexible and sustainable habits, and having the right support along the way.

If you’re ready to approach weight loss differently this year—one rooted in evidence, personalization, and long-term freedom—you don’t have to do it alone.

We’re here to help.

Mark Glesne

Mark Glesne is certified in Nutrition Science from the Stanford Center for Health Education, and the Founder of Imago Nutrition.

Mark has a passion for helping people pursue their health and body composition goals, and has been helping people reach their goals without restrictive dieting since 2008.

He and his wife Corissa have been married since 2006 and have three children: Ethan, Asher, and Maisie.

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